Bras + Body Confidence
with kimmay Caldwell
Is getting dressed a hassle? Do you want to rip your bra off at the end of the day?
Do you struggle finding bras that feel comfortable?
If you’re ready to move from Ugggh to inspired when you get dressed, you’re in in luck because today I’m talking with my amazing friend Kimmay Caldwell, an Undergarment Educator and Self-Love coach that helps people feel comfortable (and confident!) in their bras without wasting their money on bras they dread wearing.
Learn how to find a comfortable bra for your unique, beautiful body without feeling like you have to wear one. Yep! Let the old stories about why you “should” wear a bra melt away and be the decision maker of your body (and what you wear right over your heart), including no bra at all. Hurray!
Listen in to discover...
How your relationship to your undergarments can be so much more supportive.
Rituals to weave in self love and compassion into your daily routine.
What to know so you don't create shame for your kids first bra shopping experience.
How to release body shame and invite in body confidence and love.
And how to transform your everyday ritual of putting on a bra into a powerful way to uncover your confidence, stand in your power, and learn to love yourself.
Complete transcript below.
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Kimmay Caldwell is an Undergarment Educator who supports people to say hurray inside, outside, and underneath™.
She is an expert bra fitter with over a decade of experience of getting intimate with people from cup sizes A to N since 2005. Formerly based in NYC, she spent three wild years in rural Oklahoma and is currently based in Philadelphia, but she loves to travel around the world to spread her empowering message of self-love, teaching people how to use the everyday ritual of putting on a bra to uncover your confidence, stand in your power, and learn to love yourself. Her newest offering, Bra Confidence & Comfort, supports people to find a comfortable bra fit without wasting money on bras they dread wearing so they can start each day saying HURRAY!
You may have seen her in one of over 100 press outlets, including The Martha Stewart Show, The Today Show, 10 times on The Rachael Ray Show, 13 on The Marilyn Denis Show in Canada, and many magazines and podcasts. Wherever she is, you can connect with Kimmay @Hurraykimmay, and always find her at www.HurrayKimmay.comv
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EPISODE 262: Kimmay Caldwell
[Fun, Empowering Music]
Amanda Testa: Hello, and welcome to the Find Your Feminine Fire podcast. I am your host, Amanda Testa. I am a sex, love, and relationship coach, and in this podcast, my guests and I talk sex, love, and relationships, and everything that lights you up from the inside out. Welcome!
Hey, what’s up? It’s Amanda! If you're enjoying this pod, and you know you are ready to say yes to more pleasure, and you are just wanting to know, “How the hell do I do it,” well, you’re in luck because as of now, we have spots available in The Pleasure Foundation, which is my pleasure membership where twice a month you get an amazing practice that teaches you how to drop into your body, to become more connected to yourself, and to learn the art of sacred self-care. So, if this is something you're interested in, go to www.amandatesta.com/tpf (as in The Pleasure Foundation) and we will see you there!
Hello, and welcome to the podcast today! I have a question for you: is getting dressed a hassle? At the end of the day, do you feel like you want to rip your bra off and throw it away? If you struggle to find undergarments that feel comfortable, then you're gonna love today’s episode because I’m so thrilled to be talking with my friend and amazing undergarment educator, Kimmay Caldwell. She is also a self-love coach, and she really helps people feel comfortable and confident in their bras without wasting money on bras they dread wearing and also how connected, really, this experience can be, right? So often we go through our days just slammin’ and bammin’, all the things, but really taking a minute to make everything you do intentional, and I really love that about Kimmay. So, thank you for being here, and welcome!
Kimmay Caldwell: Hurray! I’m so excited to be here. I wish y’all could see what Amanda is wearing and her beautiful decor, because she is just walking the walk with what she talks over there. Her feminine fire is on fire today!
Amanda Testa: Well, thank you very much.
Kimmay Caldwell: You're welcome!
Amanda Testa: I actually have to just share one little side note is Kimmay always has great social media where she’s sharing all kinds of beautiful lingerie all the time, which, if you listen to the podcast, you know I love lingerie, and also, you don't have to have fancy lingerie to be sexy, but it feels fun when you find the things that feel good, which we’ll talk about.
Kimmay Caldwell: One hundred percent.
Amanda Testa: But you introduced me to, what is it, Empress Mimi?
Kimmay Caldwell: Ah, yes! Oh, my gosh! What a fun brand.
Amanda Testa: It’s super fun. So, now I’m on their subscription, and I just got a new one yesterday. So basically it’s so exciting, and they have beautiful packaging, but it’s got butterflies and is so springy and it’s purple. It’s perfect for the spring because it’s finally warm here. So, side note.
Kimmay Caldwell: Oh, my gosh.
Amanda Testa: It’s all fun news!
Kimmay Caldwell: Okay, well, hello, brand testimonial. I worked with them on a really great project called “Dopamine (Under)dressing,” which is an editorial that I did for Revealed Magazine, and their stuff is a dopamine hit. It’s fun colors. It’s vibrant stuff. It’s not necessarily your everyday, supportive, workhorse bra, right?
This is like fun, cutesy stuff, but their social media, by the way, is so much fun and so empowering, and that is really -- I think people purchase from them not just because they have the fun, beautiful stuff to wear, but because they know they have this brand kind of behind them. And so, oh, my gosh, I’m gonna tell them! They're gonna be thrilled. They're so great.
Amanda Testa: [Laughs] And, of course, my daughter’s name is Mimi, so, you know…
Kimmay Caldwell: Oh, adorable!
Amanda Testa: That always helps. So, I’d love to get back to the meat of what we’re talking about and how important it is to kind of find more pleasure in getting dressed, and I’d love if you would share a little bit more about why this is such a passion for you.
Kimmay Caldwell: Oh, my gosh. Love this question so much. So, first of all, there are probably some people listening who are more on the free side of life, right? They like to be free and loose and have a more fluid day, and for them that might mean they are not wearing bras. They're just like, “Nope! Just not for me. I want to feel free,” and bras may feel restrictive for them. There are also people who maybe are actually looking for support and are like, “I want to feel held in. I want to feel supported. I want to look lifted,” and yet they're probably also like, “I cannot find one that doesn't feel like I want to rip it off by the end of the day,” right?
We have so many people that are like that. And so, I want to encourage us to think about bras like we think of shoes, and I use metaphors all the time to teach. I am an undergarment educator, and so, when I talk about bras, I use many different metaphors.
So, one is they are shoes, right? So, when we think of shoes, it is possible that we could be wearing the wrong-sized shoe and that it’s not gonna feel good. So, so many people have been wearing bras that are just the wrong size or style for their body. So, imagine if you’ve been wearing a size seven shoe for years, and you could or should be wearing a nine. Of course, at the end of the day, you're gonna get home and be like, “I want to kick these dang shoes off. They feel so horrible. I don't know why I even bother wearing shoes,” right? The same thing is true when your friend is like, “Well, I really love this pair of shoes. They're super comfortable.” It doesn't matter if it’s the most comfortable, well-made, gorgeous shoes in the world that are made of actual marshmallows, when you go to put those shoes on in the wrong size, they’re still gonna feel horrible, and you're gonna feel so much better wearing slippers or going barefoot.
I hope you're following the metaphor here that if you're wearing the wrong bra size, then of course it’s gonna feel better to wear a little stretchy bralette (which would be slippers) or go barefoot (which would be wearing no bra at all). It’s not to say that it doesn't feel great to be barefoot some days or it doesn't feel great to be in slippers some days, but they're not actually super supportive, and when you're out and about in the world or you're at the gym or hiking or on a professional interview, you probably don't want to be barefoot or wearing slippers.
So, that’s how I sort of look at bras in one way, right? We have to educate people on the fit and the size before we can talk about their comfort and their confidence, and when I mean confidence, I also mean the kind of confidence that comes from high self-esteem, so liking yourself, and that takes practice. So, bras are my favorite tool to do this for a couple reasons.
One is because they can be just for you, right? They’re under the clothes, so unless you're me and you're on your social media in your underwear all the time, [Laughs] most people probably aren't gonna see your undergarments. So, it is just for you. Now, y’all can't see this, but Amanda, I’m gonna prove it to you. Today I’m wearing a gorgeous blue bra. Look at this. Stunning.
Amanda Testa: Oh, that’s gorgeous.
Kimmay Caldwell: Thank you! And listen, no one has to know. My husband might not even see this today, right? This is just for me so that I feel -- you know, I admitted to Amanda offline that I’ve overbooked myself recently, and I’ve just said yes to too much, and I was feeling a little down. So today, I put on a cute dress and a cuter bra, and I am just carrying that energy around with me.
The second reason I think they’re such a rich tool for getting dressed in the day and saying hurray is because we wear them right over our hearts.
So, if you know anything about chakras or just energy in general, even if you don't, just practice with me here. This is such a sacred part of the body, and the three things that I see limiting people the most in the bra fitting room is shame: either they're too much or not enough, right? “They're too big or they're too small. They're too sexualized, they're not perky enough,” whatever. So, some kind of shame, some kind of misunderstanding we’ve had about our worth attached to this part of our body. Confusion: “What size do I even wear? What the heck is a double D versus an E?” And then discomfort: “It’s digging in, it’s falling off. I don't feel good in this bra.”
Those three things are what I call heart restrictors. They just completely block the heart, and our shoulders round and our heart goes back and we can no longer stand tall and make those heart-led decisions. So, I mean, yes, I want people to feel good in their bra everyday, but really, I want you to put your shoulders back and make heart-led decisions, okay? That’s number two.
Then finally, number three -- there are more. These are the top three.
The number three one, I should say, is that most people I work with are wearing undergarments on a daily basis. And so, I believe in the power of the one percent. If you ever read Atomic Habits, he talks about habits being that one percent change that you make and how over the course of time it can completely redirect your life.
So, for most people, they put on their bra and take their bra off every single day. It’s a daily habit that you already have. If you could turn that habit into a ritual or habit stack on top of it and maybe say one kind thing to yourself or take just 30 seconds of putting on your bra to set an intention or to say an affirmation or to lovingly forgive yourself for an unkind thought that you had, something, anything, something small, really small. If you do that every single day when you put on your bra or even every day when you take it off as well, right (one or the other or both), imagine in one year, five years, ten years, how that practice of saying something kind to yourself or releasing a shame or affirming something about yourself will change your day and your days and your life.
That’s the power of putting on something that you love every day, and you have to start with something that actually feels good, right? It helps if what you're putting on actually feels really good and is who you want to be that day, you know?
Amanda Testa: Yes!
Kimmay Caldwell: “I want to be a bright blue bra today,” instead of, “I want to be something that I kind of am settling for.” So, all right. That’s why I’m so passionate about this.
Amanda Testa: Oh, my gosh. I love it so much. It makes so much sense because I think these little things are actually huge things, right? They're not little because, like you say, it’s the little things you do repeatedly over time that make the difference, not the big, huge things, right? It’s the little things you do, and I talk about this a lot around relationships, too. It’s like the ways you build connection or not, right?
Kimmay Caldwell: Yes. Yes.
Amanda Testa: The way you're kind to yourself or not. The way you make something intentional or not. It’s so big, and I love it so much because I think for so many women-identifying humans, people that have breasts or that want to wear undergarments that make them feel good, like you say, you've got to kind of go with what you're feeling, right? Sometimes you want to be barefoot. Sometimes you want to wear the stilettos.
Kimmay Caldwell: Yeah!
Amanda Testa: Sometimes you want to do whatever, and that’s what’s fun about it, but I think the key is I love how you say kind of going back to how you first learned to buy undergarments, because I think a lot of this is tied with so many things, but oftentimes, when we think back to puberty or what we learned about our developing bodies, what we thought about that, what people around us thought about that, how they helped us maybe shop for our first bras or whatever and how that experience was makes a big difference in how you feel today.
Kimmay Caldwell: Totally.
Amanda Testa: So, I’m wondering if you might speak to that a little bit.
Kimmay Caldwell: Absolutely, and I want to backtrack too because, you know, that point about putting something on every day, the whole point here too is that when you open up your bra drawer or wherever you throw your bras -- hopefully they're not just on the floor. No shame, but I know someone out there listening is like, “They are definitely in a pile on the ground right now.”
Whenever you open up that bra drawer, I want that person to have choice, right? That’s the autonomy of what we put on and in our bodies is so powerful. So, opening up that bra drawer and being like, “Okay, who do I want to be today? How do I want to support myself today? How do I want to adorn my body today?” That’s really a powerful moment.
So again, even just that ritual alone of asking yourself and then making a choice for yourself is really, really, really powerful, and again, if your bra drawer is filled with things that you're like, “Ugh,” about, that’s not gonna be a really powerful decision. But if you can open it and be like, “Okay, who do I want to be,” and you have all these wonderful, well-fitting, beautiful garments -- and by the way, beautiful is so subjective. It could just be a basic, skin-tone, neutral bra or it could be a beautiful blue lace bra. It doesn't really matter. It’s just like I want to make sure I’m addressing myself and dressing myself in a way that makes me feel awesome today. So, hurray! That’s that.
Okay, so then going back to how we’re taught and how this gets brought up. So, I have a really popular TikTok account, and however you feel about TikTok, it’s reaching a certain demographic that I wasn't necessarily reaching before. So, the people that I was helping a lot in the bra fitting rooms which, mind you, I’ve been fitting bras since 2005, y’all. That’s 18 years of fitting folks. In the bra fitting rooms, I helped people of every age and size and shape and need that you can think of, especially because I was in New York City. So it was with every single kind of human. And the number one demographic that I was supporting was women in their fifties (like 55 years old), and usually that was because they were desperate. They had gone through menopause or they were about to go through menopause, which is like a second puberty for the body, okay? Your body’s changing, and they're just like, “Oh, my gosh, I cannot deal.”
Then finally, that generation right before me, currently the way that most families are, their kids are out of the house. They finally have the time, the financial resources, and then the desperate need to come in and get a fitting.
So, that was my jam. Then when I started blogging and doing more television and stuff like that, I was getting actually my peers (people in their late thirties and then early forties, maybe late twenties, but really that kind of around-my-age-group people). Now on the TikTok, I’m getting girls and guys and folks who are 13, 14, 15, and I’m like, “Fascinating!”
So, I put out a couple times asking people, maybe my age, older, whatever, “What was that time like for you when you got your first bra? What emotions did come up for you,” and then I’m getting the folks who are like, “I’m going shopping for my first bra, and I’m nervous. How do I bring this up to my mom?” It’s so wild to see all these different ages discuss this, and obviously generational things and cultural shifts affect this, but I have seen in the fitting room so many parent and child duos come in, and I have seen this affect that person immediately, and then I’m assuming long term about how we address this part of the body.
If you're a parent and you remember this for yourself, great. But I want you to think about your kid because no shame here and no judgment if you didn't address it in this way and you're feeling guilty or something, right? I want to just lift that here and just bear with me here as we think about new ways to address our kids and discuss this because we may not have been given the best example. I love my mom. I wasn't given the best example on this. And I don't think she had the language to help me understand how to honor this part of the body. I grew up in 90s diet culture, so I just actually had a lot of shame around my body. I lived in purity culture, so when I first went shopping for a bra, I didn't even let her in the room. I was so embarrassed. I was so ashamed of this part of the body. Clearly, it needed to be hid or fixed or shaped in a way that was more appropriate. So that was the story I had.
Other parents, when they bring in their kids will say something to me like -- they’ll bring somebody to a bra-fitter because they just are like, “I don't know what to do with her,” and they will say that! Amanda, they will be like, “I don't even know what to do with her. They’ve gotten so big. I just can't handle it. I’ve always had small breasts. I don't even know what to do with these big boobs,” and I’m like, “Whoa, hold on a minute. Let’s calm this language down.” Or they’ll say something like, “Just don't give her a push-up bra. We don't need her attracting attention.” I’m like, “Hold on a minute.” We’re teaching that young person how to think about this part of their body as either a source of shame, a source of not being safe -- what’s the word for this, unsafety? Danger is the opposite of safety -- a source of danger, right? This might attract a dangerous person towards them, or that it might mean something about them and their sexuality, that suddenly she’s gonna be a slut because her boobs are big. There are all these stories that we’re teaching somebody about this.
So, I highly, highly encourage you to use neutral language to just really support that person to go in and say, “Listen, let’s find something that feels really comfortable in your body. Let’s learn about this together. Let’s go try some things on.”
I’ve had to rush moms out of the room and do damage control because I can see that person just shutting down and those three things lock in that person’s heart right away.
So yeah, it’s so fascinating how we learn about this part of the body from others around us - from our parents, from our culture, from television, from our peers. A lot of my job is helping people to erase and unravel those stories and literally get stuff off your chest. Just let it go. Let it go. Undo it.
Amanda Testa: That is so amazing, and I am so glad that these people had you in the dressing room with them. If only all fitters were this knowledgeable and helpful.
Kimmay Caldwell: I know. [Laughs]
Amanda Testa: Because I will tell you, though, I recall I have a specific memory of when I was in high school, and same. I grew up in the 90s, too, with that heroin chic, the very --
Kimmay Caldwell: Yep. Totally.
Amanda Testa: That was what was in, and I’m a curvy person. That was not my body at all, and I remember I was trying on bathing suits with my friend’s mom. [Laughs]
She had a lot of opinions, and so, I remember I tried on this bathing suit, and she was like, “Hell no! That’s like two boobs walking forward!”
Kimmay Caldwell: Oh, boy.
Amanda Testa: She was like, “You cannot have that one.” I always had a lot of shame about my boobs being big, you know? I just share this because I think people listening that have that -- you know, we do hold so much here because then we maybe even kind of hold our posture differently.
Kimmay Caldwell: Yes. One hundred percent.
Amanda Testa: We curve in and don't stand up straight or feel straight. Again, our bodies are our bodies, and people’s responses to that are not our responsibility, which is the other thing that we’re taught as kids, right, especially when saying, “That’s not appropriate,” or the most conservative, hideous bra that I could have had were the ones that my mom bought me. [Laughs] And I didn't know different.
Kimmay Caldwell: Yeah.
Amanda Testa: I was like, “Oh, just whatever.”
Kimmay Caldwell: And it’s always for somebody else’s comfort, right?
Amanda Testa: Mm-hmm.
Kimmay Caldwell: Right? And if I’m being really honest, it’s always for the men. We don't want to make men feel uncomfortable. We don't want them to get aroused. We don't want them to be distracted. Like, what?
Amanda Testa: Yeah, that is the purity messaging right there, right?
Kimmay Caldwell: Exactly.
Amanda Testa: It’s our responsibility.
Kimmay Caldwell: And so, we have to cover our nipples. God forbid we had a natural breast shape in a T-shirt and walked out into the world. We would be seen as absolutely inciting flare-ups of attention, and yet I think about when I’m around my girlfriends, we don't care if we see each other’s natural breast shape. People will say, “Well, that’s because you all have boobs.” Not really, and also, you know, again, it becomes this safety issue of I don't want to make that person uncomfortable, but also I don't want them to start to think of me in a way that makes me feel unsafe.
So, I have feelings about how I wish we could free the nipple and I wish we could have that natural shape and that we didn't need bras at all (like, how feminist of me), and yet, I also agree and disagree. I know I actually love wearing undergarments. I love adorning my body with that sometimes, right? I love going free sometimes. And then also I know that’s not the current culture we live in. So, there are certain standards and there are certain safety measures that I take in order for me to function in this world and feel like I am a safe and secure person. So, it’s tricky. It’s really tricky, and I told my husband the other day I actually wish I lived in a time, like prehistoric times, and I said, “I wish we could just go back to when we were all just naked and no one cared and it just didn't matter,” but we can't, you know? We can't do that.
I also want to add one thing -- oh, go ahead.
Amanda Testa: No, you go ahead.
Kimmay Caldwell: I wanted to add one thing about how you wish everybody could have a bra-fitter like me, and listen, I don't think I’m the best bra-fitter in the entire world. I’m pretty darn good, and I definitely have a great sense of compassion, and I bring that into the fitting room. I also bring in things like crystals and I bring in things like oils because I think we can make bra shopping a sacred experience, right? So, you're gonna get something different with me than you would maybe with someone else. That said, everybody I would fit at 55 would be like, “Oh, my gosh,” like I’ve totally blown their mind. I’ve educated them on what bra sizing even is, on how their bra should even fit, and they're like, “How in the world did I go 40 years wearing bras and had no idea about this? Gosh, I wish I met you when I was 20,” and I go, “Me too. Do you know a 20-year-old? Please bring them to me!”
Because at 20, most people -- and this is a gross generalization, but a lot of people are kind of perky enough that they can kind of fake it in a bra, and they’ve got so many other things going on in their life that they're just like, “Who cares,” that they're not coming in for that level of support.
And so, I actually, when I was living in rural Oklahoma -- so, y’all, just for context, I lived in New York City where there are lots of bra shops and wonderful locations I could send people. Then I moved to rural Oklahoma, which is like a whole other podcast, okay? It was like Schitt’s Creek happening. It was very crazy. It was a very strange time in my life. Three years I spent there, and one of the best things I think I did, besides hosting a full-moon circle, which, gosh, I thought they were gonna run me out of town on my broomstick because I’m always a little too Jesus-y for my woo friends and a little too woo for my Jesus friends.
Either way, that was one thing, but the second thing was I hosted a bra and periods talk at one of the local high schools, and these were a bunch of young people from, I think we ended up doing grades 6 to 12, which was a big group, a vast difference in bodies. And I remember so clearly that these young people did not even have any basic information about their own body (their reproductive organs, their breasts, their bust, nothing), and a lot of them had no one to ask, no one to talk to.
In addition, this isn’t kind of important to say for this particular group, but this is in general, this applies in general, but for this particular group also, a lot of them were from a particular religious sect that also didn't believe in going to doctors. And so, they did not take medicine. One girl, actually, she played basketball. She was very seriously injured, and she did not go to the doctor to get that looked at or taken care of.
They can't even take Ibuprofen for cramps, so this is kind of an extreme example, but my point is they didn't have a doctor or a health professional to ask questions about their body, including their bust. So, I was sort of it for the day, and it felt so good to talk to these young people from the start about how to address this part of the body, not just how to find a bra that fits, but how to love yourself a little bit, how to be easy on yourself.
They asked the best questions. One question was like, “If the boobs are bigger, are the nipples bigger, too?” I think she literally was curious, like, “Are my nipples an okay size,” and that was a great question! They were just so engaged and had so many questions, and there were lots of questions about binders and queer folks that you could tell that person either asked to challenge me and didn't know who I was or wanted to make sure they weren't forgotten or left out. I was like, “Great question!” And I said, “By the way, does everyone know what a binder is?” And people were like, “No,” and clearly felt a little uncomfortable. Then I said, “Would you like to tell them or should I,” and this person got nervous and was like, “No, you can.” It’s like, “Great!”
We just addressed it like it’s another undergarment: “That’s it. Great! This is an option for folks who want a flatter front. Awesome.” We addressed it a little bit, and then we moved on. So, just normalizing things that I think feel very uncomfortable for young folks is so, so, so important, and letting them know that a trusted person who’s kind of cool -- like I’m not your mom, right? I’m not even your aunt. I’m a cool person who you can talk to but also look up to and respect a little bit.
So, okay, anyway, I’m saying all of this because I want to do more of that, so if anyone’s listening and you work at a school program, please let me know. I’m gonna train other people to do that, to go in and empower young folks, and this year I’m actually starting a bra fit training. So, I already have a great course (which we can talk about later) for people who wear bras, but people always come to me every time I’m on television, they're like, “Where can I get a fitting in my town?” When I was in New York City, it was so easy for me to send you to someplace. Then I moved to rural Oklahoma. People were driving two-and-a-half hours, Amanda, to go to get a bra, and it was at a Victoria’s Secret, and I was like, “Oh, God, no! We’ve got to change this. We need to get you to a real fitter. We need to get you to a place where this person understands bras.”
So, that’s my goal this year is to make more compassionate fitters, people who can not only fit you for a bra but also create a safe and welcoming environment where you can ask questions, where it’s okay if you're like, “Is it normal if one of my breasts is bigger than the other?” Like, “Yes! Totally normal. Let’s talk about it.” So yeah, that’s on my heart big, big, big time. So, I just wanted to go back to that.
Amanda Testa: I love that because I wanted to loop back, too, and I’m like, yes, I know a lot of people that are listening to the podcast are of the age where their kids maybe are past that or not, but I know my daughter is ten, so we’re about to ride these waters, and I would love for --
Kimmay Caldwell: Okay!
Amanda Testa: -- those listening, like, what would be maybe two tips that you would give them when they take their kiddos undergarment shopping? What would you offer?
Kimmay Caldwell: Yeah.
Amanda Testa: What can they do to make it a safe and nurturing experience versus -- yeah.
Kimmay Caldwell: Great, I’ll make this -- yeah, no. Absolutely. I mean, number one: your intention means everything, right?
So, what is your intention throughout this process? Is it just, “Get them a dang bra that fits,” because that’s what you’re gonna get, or is it, “Let’s practice honoring your body and being open and creating an open relationship together so that I can support you”? Also ten, by the way, is the number one age when people get their first bra. So, you're in it, babe! It’s bound to happen one of these days! But it goes all the way down to 5, believe it or not, and all the way up to 15, but 10 is sort of that median age of when most people get their first bra or at least are introduced to the idea of wearing it.
You can also really just pay attention and see are their peers wearing bras? Is this something that you want to bring up where you think they could be ready but they're not talking to you about it, or do you want to wait for them to bring it up to you? There’s no wrong answer here, but just letting them know it’s safe for them to talk to you about it and be like, “Hey, I don't know if any of your friends are wearing bras yet, but if you ever want to talk to me about that, I’d love to talk to you about that.”
Just really letting them know, and they might be awkward and weird like, “Mom! Ew! Bras!” or they might surprise you and be like, “Yeah, I think Tracy wears bras, but I don't know, she has bigger boobs than me,” and then, “I don't think I really need one.” You can be like, “Great, let’s talk about that,” right? You never know what that situation’s gonna bring. Okay, so that’s one.
Two is to educate yourself. Please, oh, my gosh, please. Again, I told you everybody I fitted was in their fifties and had no idea how a bra was supposed to fit or how bra sizing really works. We have just been on this loop of misinformation playing the worst game of telephone in our entire lives of parent to child, usually, of just passing down misinformation about bra sizing, bra fit, all of this stuff, and mostly it is, again, very shame-based that a triple D’s the biggest thing you're gonna find. Y’all, the most popular bra sizes that I fit on a regular basis are 32F and 34G, every day. So, if you're like, “What? That size even exists,” I fit up to N cup.
So, educate yourself. Understand how bra sizes work. I have so many free resources on this. I also have a paid course on this, so you can be informed for your own body, and then you can help inform and change the life of this person that you are in care of. [Laughs] So, that’s number two.
And then number three, I always suggest going to a really great bra-fitter, you know? You don't have to guess this. You don't have to bring them into a department store with funky lighting and a sea of bras that you don't know how to get through. Bring them to a professional. Make it a really positive day. Go for mani/pedis or a lemonade or ice cream, too. Just make it a really fun, awesome experience and be like, “Let’s go bra shopping together.” Again, they might surprise you. Your kid might be really awkward and uncomfortable about it or they might be like, “This was the best day ever! How cool!”
Then, finally, is just let go of any shame you have yourself so that you're not passing it on. That’s a daily practice of really letting go of what it means to wear a D cup or what it looks like to wear a 30 band instead of a 38 band or whatever. Let go of the numbers and the shame and just really, really practice that for yourself so you're not passing it down.
Amanda Testa: I love that, and just, if you would because I know this is a project that is also near and dear to your heart that you’ve done before, but I love when you talk about how you’re not your numbers, which is so easy for us to judge ourselves in this culture that we’re in versus kind of -- I feel like things are getting way better in regards to just --
Kimmay Caldwell: Sure.
Amanda Testa: -- encouraging whatever is and just embracing who you are and the way you are, but it’s still challenging out there. And so, I’d love if you would share a little bit about how to do that.
Kimmay Caldwell: Yeah, and I want to point out that, you know, you and I are intentional about lifting those things, and we are moving in those circles, so to us, we’re like, “Look at the changes! How amazing,” and at the same time, you know, there are more filters than ever on Instagram, and there’s a lot of false advertising around what your body’s supposed to look like and the standards that we’re setting.
And unfortunately, I don't have an actual stat to back this up, but I actually know this is true that we have more young women, specifically, (like teen girls) unaliving themselves than ever before, and we believe it’s because of this pressure of what they're seeing on social media. And so, when I talk about being more than your numbers, I’m also talking about really being honest and truthful with yourself and not feeling any shame around it. So, I just want to point that out that that still exists and we have a lot of work to do. So, hurray!
So, the More Than My Numbers Project is something very dear to me, as you mentioned. I started this in 2014/2015, and it was because every time I fit somebody for a bra and I wrapped the measuring tape around them, I could just see them trying their best to be smaller. We wanted to have a low number. We want to be a small size. We want to be dainty and delicate. And then they look at me and be like, “What am I? What am I? Tell me my bra size,” and I would be like, “Well, hold on a minute. First of all, this measuring tape can only just tell me a starting size, and then we’re just gonna try on bras together, and you might be different sizes in different things,” and I kept saying to them, “You're more than the number.”
I also would tell them, not to discount here, “You also aren't a number.” When people say, “I am a 34DD or I am a 36B,” it drives me bananas because I’m like, “That’s not who you are. You are a divinely created human being. You are generous. You are luxurious. You are compassionate. You are whatever. That’s who you are. This number just happens to be this size in this particular bra that fits best on your body today, and it could change in a week,” [Laughs] like truly change.
So, I caution us to claim those numbers as who we are and instead to use numbers as information and not a definition. So, the More Than My Numbers Project sort of started from let’s start with bra sizes and then try something else, too. There were other numbers that we’re really letting define us: our salary, our age, our weight, the number of pregnancies that we’ve had, the number of kids we do or do not have. There’s just so much about numbers that I just felt ready to let go.
So, I started that then. I did two rounds of this with people of all different sizes and ages and abilities, and I used other people because I constantly was using myself as an example, and I tell people I wear a 32DD, and they’d be like, “No way! Double-D?” Because they think Dolly Parton, and I had quite petite breasts. Thirty-two double-D ain’t that big, y’all. Again, we could talk about why (because of sister sizing), but it was such an eye-opening thing for people to then see other humans of other sizes.
So, now this year, 2023, I’m doing another installment of this project with a really cool magazine that I work with a lot, and I’ve grown. My numbers are different. I’m so excited to share other people’s numbers, and again, to really get it out there that numbers are important to know. It’s great to know your starting sizes. It’s great to know your bust and your underbust measurements so then you know where to start in the bra alphabet. But that’s not actually who you are. You are so much more than your numbers.
So, yes, say it loud and proud with me, y’all: I am more than my numbers! Ooh, you’re muted. You’re muted.
Amanda Testa: I love that! I was just saying out loud: I am more than my numbers.
Kimmay Caldwell: [Laughs]
Amanda Testa: It’s funny, too, because I’m 49 now, so I’m in the perimenopause. It’s happening, and my boobs are enormous, and they hurt.
Kimmay Caldwell: Yep. Yep, yep, yep.
Amanda Testa: And I can't not wear a bra because I usually don't like to wear one. It goes off and on, right? Today, I have my, I say Mary Jo, everyday bra just for my everyday bra. But I notice -- I even bought some really sheer jog-bra things, I don't know what the proper terminology is in the bra-fitting world.
Kimmay Caldwell: Yeah, like a wire-free style?
Amanda Testa: Yeah, they were just Amazon, cheapy things, but they're so comfortable. But they just give some support because it hurts.
Kimmay Caldwell: Yeah.
Amanda Testa: It hurts sometimes to not have anything. So I just say that because everything changes, and it will shift, and that’s just part of life, and it’s not a big deal.
Kimmay Caldwell: Oh, my gosh. One hundred percent.
Amanda Testa: And I love, too -- I think, well, probably because you being a bra-fitter, seeing tons of boobs and iterations of chests over your life, and I as well, working with women and doing a lot of the work that I do and holding retreats, the more you see the way different bodies look, the more you're like, “Oh.” That’s the thing. We don't have that exposure, right?
Kimmay Caldwell: Oh, my gosh. Yes. I mean, Amanda, the number one thing that changed my life was to be a bra-fitter at age 20. I’d literally turned 20 in my second day of working, or something like that, in New York City. I think everybody should be a bra-fitter for one week. Just come see what’s in the fitting room, and not only see bodies but also it’s such an intimate space that people will reveal so much to you. It becomes like therapy almost, like where people just shed their clothes, shed their stories, say things into the mirror that I think they would never say to anybody else. It will open your mind. It changed my life, working in a bra fitting room for a year. I mean, I’ve been doing it for 18 years. But that first week, my life changed. So, I totally hear you.
And yes, boobs usually get bigger during perimenopause, and it is a really big surprise to a lot of people because they're like, “They should stop growing by now! I’m an adult woman. What the heck?” It’s because our hormones so highly affect our breast tissue, right? Estrogen is the number one effect (that and fat) on your breast tissue, and that’s all they are! I mean this lovingly that breasts are basically bags of fat attached to your body. [Laughs] So there are no muscles. It’s just tissue-attached ligaments to your chest. So, once they grow or change or droop, it’s really hard to pump them back up, and that’s kind of the job of a bra.
The number one reason -- well, I should say the number one reason most people wear bras, actually in the USA and Canada (because we’re so prudey) is actually for nipple coverage and modesty, right? It’s really because they don't want to offend that other person with the natural shape of their breast, right? That’s number one. Number two is actually comfort. It’s weird because I think a lot of people think, “Oh, my gosh, bras are so uncomfortable.” But that’s actually the number two reason in my unscientific research of many years that people actually wear bras.
I’m in that camp. I wear a 34DDD, which some people in their mind might be thinking, “That’s enormous.”
It’s not actually that full, but it’s full enough that when I’m sitting -- and I have a full enough body with soft rolls and stuff that when I’m sitting, if I’m not sitting straight up or I’m not laying down on my back, I get that skin-on-skin contact, from my breast to my torso that just drives me bananas. It is sweaty. It doesn't feel good. It’s sticky, and also, my bust the week right before my period is so tender, so sore, needs a little hug, needs a little hammock, needs a little something.
So, that’s why even people wear bras at night because -- again, wire-free, stretchy bras at night, by the way. But because they just want that little bit of hug or that little bit of separation of their breasts. So, yeah, totally normal stuff happening over there, and I bless you as you go through this.
Amanda Testa: A little hug. Okay, so, I am curious. I know that I love this conversation, and you have so much goodness to share.
So, I’m curious if there are any last really important things that you want to make sure the listeners really take to heart today?
Kimmay Caldwell: Let me think about this for a second. What do y’all need to hear? I would say I’m gonna lift some guilt someone might be feeling. It’s okay if you don't know what size bra to wear. It’s okay because, number one, we were never taught this stuff. Like I said, the majority of y’all didn't have me in your high school teaching you about bras, and you might have had a really lovely, well-meaning parent who also didn't know about bras and taught you some misinformation, and you’ve probably been guessing your entire life what bra size you should wear, and you might even have a size in your mind that fits your current identity but doesn't actually fit your body.
So, I just want you to take a deep breath and release any shame or guilt that you have that sometimes people come in and they're like, “Well, it’s my body, and I should know better than anybody,” or, “How embarrassing that I’ve been wearing bras for 30 years, and yet I don't even know how bras freakin’ work?”
Let it go. It’s truly okay. Here’s another great metaphor. You are the car owner; I am the mechanic. So, I never ever owned a car in my entire life (I lived in New York City) until I was 34 years old and moved to Oklahoma. And so, I had to buy a car in Queens and then drive it three days through a million states to get to Oklahoma, and now I had this thousands-of-dollars investment and had no clue how to care for it. I was Googling. I was asking people. I literally didn't know what a tire rotation was. That is how not knowledgeable I was about this, and yet, I was driving this car every single day.
Y’all are out there wearing bras every single day owning this beautiful body, and you're like, “I don't actually know what I’m doing here. I’m guessing.” And when I went to the mechanic or the bra shop -- follow my metaphor, here -- I felt intimidated, and I didn't want them to take advantage of me. I remember this poor guy, oh, my god. I was trying -- I had my best New York City attitude on, and he came out to show me the cabin filter and be like, “Do you want to change this?” “No, I don't want to! I’m just here for the oil change! Thank you, sir! I don't need unnecessary things like that.” I was such a jerk about it, but it’s really because I was not knowledgeable.
I didn't even know what a cabin air filter was. I was like, “What did he just show me? Where did that come from in my car?”
So, I decided to educate myself, and I took a course. It’s made by this wonderful queer person who really made it for queer folks and femme folks who might feel intimidated in the mechanic shop, and it was really basic. At first, I felt a little embarrassed that I didn't know this stuff, and then I was like, “Hold on! This is why I’m here,” and it was so empowering for me to just learn the basics. Did she teach me to be a mechanic? No. I didn't need to be the mechanic. She just taught me the basics of owning a car, when to take it to the mechanic, how to talk to that mechanic, how to be a more informed person so I understood how to look at the manual and what to do. It was so awesome.
So, that’s how I look at bra-fitters. We are the mechanics. Come to us for help. Buy my course so that you can learn, just like I did with hers, right? It’s not gonna train you to be a bra-fitter. It will just help you understand the basics of bras, bra sizing, bra styles, how to build your basic bra wardrobe, and then also how to turn that into a ritual and how to love yourself and your body through the process, how to deal with your body when it’s changing (that’s one of my favorite bonuses), how to deal with your body and bra sizes as they change. I don't just mean practically but lovingly how do you address your body as it changes. I also have a really great bonus in that course on pregnancy and postpartum because, again, huge time of change in the body in great need of support.
Amanda Testa: Yes, yes, yes.
Kimmay Caldwell: So, yeah. That’s my final thought, I guess, is don't beat yourself up if you don't know this stuff and you’ve been wearing bras for 30 years and you're like, “Why the heck didn't I know this,” and go get yourself educated. Like I said, I have free resources. I have a great course, and there are phenomenal fitters besides me or me who can support you.
Amanda Testa: Yes, thank you so much. It is life changing. I think the first time I went to get a “real bra fitting” I was probably in my thirties (like early thirties).
Kimmay Caldwell: Good for you! That’s early, babe! Good for you.
Amanda Testa: So yeah, it was life changing.
Kimmay Caldwell: Yes! And don't you wish you had gone earlier?
Amanda Testa: Yes! I mean, granted --
Kimmay Caldwell: It’s never too early. It's never too late.
Amanda Testa: I was very much --
Kimmay Caldwell: Yeah, yeah.
Amanda Testa: -- a hippie living in the mountains, so probably didn't really wear bras as much.
Kimmay Caldwell: Okay, fair.
Amanda Testa: But I will say I love -- it’s just fun. I’ve learned to find the ways to make it feel good, and I think also, I like to dress up and have fun and play, and for me, it’s just a fun way to adorn myself. So, it never fails if I’m feeling not good or if I’m feeling bloated, yucky, then I just put on some beautiful red panties and a beautiful red bra -- I have so many different -- and that’s the thing. I have things in different sizes depending on when it is in the month.
Kimmay Caldwell: Uh-huh.
Amanda Testa: I know my body changes.
Kimmay Caldwell: Yes, good for you.
Amanda Testa: That’s the other thing is knowing when you go in your drawer there’s something in there that fits, that makes you feel good. No matter what size you are, that feels good.
Kimmay Caldwell: I was just gonna say if someone’s listening, maybe if they’re listening to your podcast they know about adorning their body and wearing beautiful things and pleasure. But even if that’s not your jam, even if you're like, “I don't like lace. I don't like color,” whatever, literally the baseline of having something that fits and feels good, again, it’s like putting on a glorious shoe that you're like, “Oh, my God, I could run a mile --,” I was gonna say a mile because that’s my threshold. [Laughs]
Amanda Testa: Yes.
Kimmay Caldwell: “I could run miles in this! I could run a marathon,” right? It feels so much better, and then you carry that comfort and that confidence and those shoulders back and that heart out with you for the entire day.
Amanda Testa: Right. It’s so true. Thank you so much. I so appreciate you being here, and yeah, can you just let everyone know where to find you and your course and all the good things that you have to offer?
Kimmay Caldwell: Yes, so all my handles and my website are Hurray Kimmay, www.hurraykimmay.com or @hurraykimmay on Instagram or whatever, and I’m literally one of those people that if you're listening and you want to reach out on Instagram or something, please do! I literally want to hear from you. Let me know what you think about this conversation. Let me know what questions you have, please.
And then if you want to get in touch and check out my course which is called Bra Confidence and Comfort, Amanda and I have a little bonus for you. So, you can go to www.hurraykimmay.com/amandatesta and that will bring you to our main landing page where you can opt-in and get a free Fit Guide, and that free Fit Guide will kind of get you started, and then there’s a class as well. In that class you’ll be guided to see if this course is right for you. It’s totally up to you, and you’ll get a special discount if you go there.
If you're already like, “I’m in! I’m sold! I just want it. Give it to me,” you can go to www.hurraykimmay.com/bcc, and then use code FIRE100, and you’ll get $100 off that course.
If you're just like, “I don't even need the Fit Guide. I’m ready,” go for it. I’m happy to support you in that way. Again, I’ve got lots of free resources and wonderful things for you on my website and on my Instagram and my TikTok and all those wonderful places, too. So, hurray!
Amanda Testa: Hurray! Thank you so much, Kimmay! For those listening, please make sure to follow her. She’s so fun and will inspire you with ways to feel good in finding the undergarments that are right for you! And so, thank you so much for being here, and thank you all for listening!
Kimmay Caldwell: My pleasure. Thank you so much, everybody! Amanda, thank you. This was a wonderful conversation, and I really truly appreciate you.
Amanda Testa: Yes, thank you, and we will look forward to seeing you all next time!
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Thank you for listening to the Find Your Feminine Fire podcast! If you loved this episode, please go ahead and forward it right now to someone who you know would love it, and if you’ve not yet had a chance to leave us a rave review on Apple Podcasts, please make sure you rate and review if you enjoyed the podcast as well as make sure to subscribe so you never miss an episode. Thanks for listening, and we’ll see you next week!
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