Let's Talk About Bras - Cupcakes & Cashmere

Let's Talk About Bras

An unedited and candid talk on all things bras (and our thoughts on lingerie!).
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The other day in the office, our editorial team lunchtime discussion veered to bras—our favorite styles, how often we purchase them, and why it's so hard to find a perfect strapless option (a conversation that isn't entirely rare in a mostly all-women office, sorry G). After Leslie revealed to us that she hasn't purchased a bra since high school—at which point, we all just about lost it, but she stood firm—we decided we needed to hit record and get our conversation on tape. Read on for an unedited transcript of our discussion, and add your own thoughts in the comments below, or on our Facebook group:

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Emily (DD-cup): So I think bras fall under the category of things that we all obviously need and wear, so it's kind of weird that they're something that we actually rarely talk about as women. And Leslie—you just revealed some of the bras you have are literally from high school... 

Leslie (VP of Content, C-cup): By 'some' I should probably clarify I mean 'all.' Which makes me sound disgusting, but honestly I'm surprised to hear that nobody else does this because it's just one of those things—I don't like shopping for them, I have a really good nude basic bra and a really good black basic bra. They fit, they work, they're not gross, and I wash them every week.

Kelly (Marketing Manager, B-cup): How are your bras not stretched-out? Is there underwire poking through? My bras pill... I don't know exactly how many years it's been since high school...

Emily: I mean we're looking at twelve years?

Leslie: Yeah. Well... yeah, I'd ballpark twelve. Oh my god okay, yeah, that's a long time, but they're in good shape! 

Emily: Also, getting a little bit more personal here, it's also not a thing just based on breast size because Hannah and I both have larger busts, so I think we both assumed that this is because you have a smaller bust, but Kelly you're—

Kelly: I'm on the small bust train and I don't think I've had a bra longer than 3 years, and that's the longest, except for maybe one or two that I don't wear often. At that point, they're stretched out and need to be thrown away.

Leslie: See, mine have not stretched out. And it's not like I have some really fancy bras—I'm talking Victoria's Secret basic bras. It's not even a fancy expensive bra necessarily...

Kelly: Do you not, like, want a new one...?

*laughing*

Hannah (Graphic Designer, D-cup): I constantly wear the same bra, and when I've worn it like a thousand times, I'm just like, ugh!

Emily: You're over it!

Hannah: And it's not even like it's dingy or actually gross, I'm just like, I've worn it so many times....

Emily: You want to be inspired by what you're wearing—I think the same argument can be made for workout clothes. I had an intervention with my mom a couple years ago because she was wearing the same ratty, dingy workout wear that she had worn to the gym when I was a child—we're looking at like twenty, thirty years...and she just didn't consider it!

Leslie: I'm totally on Faye's side here! I've had the same Lululemon leggings since my mom and I went to Canada in maybe my sophomore year of high school. We came across a Lululemon store in Halifax, which didn't exist in the States yet, and were like, this is the best thing we've ever seen!

Emily: I don't understand that! Those pill for me after a year.

Kelly: Agreed.

Emily: But again, maybe this conversation should be more about, what kind of detergent are you using, Leslie? [laughs]

Leslie: I am an excessively sweaty person when I work out, but I just wash my clothes and then they're clean! 

Emily: To be fair, we can also lump Caroline into this camp so it's not just everyone jumping down Leslie's throat, because Caroline also admits, though you're younger, you also have bras that you've worn since, ahem, middle school.

Caroline (Editorial Intern, A-Cup): And Lululemon as well—I also went to the same store in Victoria, Canada with my sisters and my mom and I have a pair of leggings that are probably twelve years old now, and I still wear them to this day, and they still fit. Though they're a little shorter, since I've grown taller...

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Hannah: But here's my question—have your boobs just not grown since high school?

Caroline: My bras were a little roomy when I bought them... 

Leslie: See, my boobs got smaller since high school because I think I was like fifteen pounds heavier.

Emily: I was actually, too. 

Kelly: How many bras are you rotating through? 

Emily: It sounds like Leslie has two...

Leslie: [laughs] Confirmed.

Caroline: I have three.

Leslie: So, okay, here are the bras that I own: I have my two basic bras—one in black, and one that matches my skin tone, which are my go-to's, then I have a strapless Natori bra.

Emily: Do you have one sexy-time bra?!

Leslie: I have a sexy-time bra, but I never wear it. 

Emily: Poor Jonah...

Leslie: [Laughs] I actually think lingerie is an interesting topic because I have a couple of sexy black bras that my mom got me from La Perla—two beautiful ones—and they're gorgeous and look great, but they just don't work that well under clothes and they're hard to wear. If I go out on a date with Jonah and I'm wearing a strappy black tank top where you can kind of see the lace underneath, and it looks cute, great, I'll wear it. But most of the time if I wear a black lacy bra under a regular top, it looks lumpy... 

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Emily: I get it, I mean for me too on a day-to-day basis, I'm wearing my Natori Feathers bra which I have bought and rebought probably a dozen times. But again, I think this brings up two things: Number one, I have a big bust so there's only so much these straps can hold up because, um, boobs are heavy. And, number two: I'm not as good as you claim to be about washing mine so I'll definitely push it.

Kelly: Yeah, I wash mine maybe monthly.

Caroline: I wash mine more like weekly. 

Hannah: I think right now I probably have eight to ten bras in my current rotation and don't wear one more than once a week, so I don't necessarily need to wash them weekly. 

Emily: So how many times do you wear a bra before washing it?

Kelly: I think it really depends...

Emily: Give me a ballpark.

Leslie: Four.

Caroline: Three to four. 

Emily: I'm getting embarrassed here... mine's like four weeks! [laughs] But I smell it every time I put it on, I'm like, 'we're good!' 

Leslie: Do you hand wash your bras?

Emily: I don't even know if hand-washing is the right word... 

Leslie: I don't...

Emily: Oh these are going into the wash?!?!

Leslie: Mmhm but I hang them to dry.

Emily: Doesn't matter, I'm still... how have those lasted as long as they have?

Caroline: The number of times I have washed my black Calvin Klein bra from seventh grade... probably over 300, 400 times now, and it holds up great! It's the best bra ever.

Leslie: I think I've owned six bras my entire life.

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Emily: So at different stages of my life, I dedicated a good portion of my salary to lingerie. In high school, that was like a big thing for me. The girls all went to the Macy's intimates section and it was really expensive. And then, you know, anytime you're dating a new guy, you want to feel good, anytime you break up with someone, you're like 'I want to still feel good.' For me, lingerie has always played a really important role in my self confidence!

Kelly: I totally agree with that because I was either single or in short-lived relationships for basically my entire twenties, and the idea of wearing the same bras throughout all those different people I dated would just be strange to me! It felt like I always just needed to 'refresh' on relationships but also on clothes, and that extends to bras for sure. 

Emily: And I'm also not someone who typically will buy one thing in multiple colors and so for me, it was even a change of pace once I found my go-to bra, the Natori Feathers—again, this is not an ad, I've been consistently obsessed with this one bra for years and years—I have purchased the same dark nude that you can't see under white clothes and I'll sometimes get a black one in there too. But I have repurchased the same thing over and over, and I used to take issue with that, thinking it took all the fun and spark and any of those other feelings that I used to associate with buying lingerie, but, at the same time, I knew it worked really well and so it's kind of like why change it. 

Hannah: On the other side, I am the kind of person who buys things in multiple colors when I find something I like, which is a habit I need to get out of because I will buy the thing in multiple colors upon the first purchase, and then I get home and don't actually like it as much as I thought. So I have done that with bras where I find one that I like, and then I'll go back the next week and buy it in a couple other patterns, and then I don't really like it after a couple months because it's not comfortable enough or because the underwire is poking through or whatever, so I think that's part of why I've owned so many bras in my lifetime. 

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Emily: So in terms of what you guys all look for when buying a bra... here are the things that are most important to me: lift, pushing together, and being able to be worn with white because I wear a lot of white. Those are the most important to me... Leslie I would assume yours is all about comfort? 

Leslie: Basically comfort--

Emily: And nostalgia— [laughs]

Leslie: [laughs] Basically comfort and nostalgia [jokingly]; if I didn't wear it in my teen bedroom, it's out! But also, I was thinking when you were talking about lingerie, I also really always wanted to like lingerie and I used to when I was younger. In high school and college I would buy a lot of lingerie but I've never felt sexy in lingerie, and I think I realized with time that if I don't feel good in lingerie, it's not going to translate.

Emily: Totally, and I think that's an important thing to recognize. It also could mean that you just haven't found your thing. For some girls, it's the really sexy push-up lace this and that, but maybe yours is a little more demure and sweet. 

Caroline: I also tend to like bralettes as lingerie instead of underwire bras and since I don't really need that much support, I can wear a lacy bralette and that feels better to me than a push-up bra. 

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Emily: Well the other thing that cracks me up about all of this is just how much my taste has changed since high school. I mean looking back at some of the panties that I wore, it was just gross stuff that would say 'follow me' bedazzled on the butt and that's just not who I am anymore, so I think it's also interesting to see how you've progressed over the years. 

Kelly: Yeah, my bra taste has totally changed. In college, I'd wear the super push-up bras and maybe that was just the product of being in college, but then over time, I'd wear less padding and less and less until it was basically no padding at all, and like you were saying, Caroline about the bralettes... I'm a small-chested person, I'm a 32B so I can totally pull off a bralette.

Emily: And embrace that instead of trying to go against it. And it's funny, I'm just getting to the point where I'm wearing slightly more fitted things, slightly more revealing, not even over-the-top or anything, but because I'm a larger chested woman, if I wear a simple tank top that happens to be tight, it looks quite out there. I mean, I'm 35 and have gotten to a place where instead of just trying to drown constantly in over-the-top billowy pieces, I'm embracing even that, as well. 

Leslie: I generally don't like it when any cleavage shows on me. I just don't think it looks good...

Kelly: I just don't have any... I think for a long time I was trying to create cleavage, but now I'm 29, I don't care anymore. So pretty much the last thing I look for in a bra is sexiness. 

Caroline: I think times have changed, too, where people used to get breast implants and that's not as big of a thing now because people are embracing smaller chests and the 'no-bra' look.

Hannah: So I have another question. I feel like so many of the bras I have are for different occasions or specific outfits, is that a factor you all consider? I often don't buy a piece of clothing because I think it will be so annoying to wear a bra with. How do you deal with that with only having three bras, Leslie? I feel like I don't even have enough to accommodate those pieces.

Leslie: I don't have anything that doesn't work with my strapless bra. Or if it goes low, I just don't wear a bra.

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Hannah: How many exercise bras do you have?

Leslie: I have a bunch, like 10, because those I have to wear everyday and wash everyday so I have enough that can get me through at least a week and then extras just to have. Those, I probably need to replace... they're also from high school and are basically for show since they have zero elastic at this point... 

Emily: I haven't done cardio in a long time, but I remember the first time I splurged on a truly incredible workout bra for larger chests, and up until that point, I had to double up. I literally had to put two sports bras on so that I wasn't just horribly uncomfortable when I would go for a run or something, and that was just a game-changer.

Hannah: Yeah, I don't run, it's just not enjoyable for me and it never has been, even with the correct bra. It's as if you have like 8 pound water balloons just attached to your chest. 

Caroline: See, if you told me I had to go for a run without a bra right now I would be okay, I could totally do it. 

Kelly: Right, I could do it too. I would notice, but it really wouldn't be that big of a thing. That's just something where we'll never know what it's like to work out with a big chest. 

Emily: And things have even changed since having a kid, where I used to get away with wearing certain things and going braless, but you just need a lot more support after you've breast-fed for a long time. Regardless of whether there's even a dramatic difference between what my chest looks like now versus what it looked like before Sloan, I just feel more self-conscious about it.

[G walks past]

Emily: Um, really glad he has headphones on right now. [laughs] Do you guys have trouble with strapless bras where they fit initially and then after a few wears they just don't?

Hannah: Yeah, I hate strapless bras so much that I've stopped wearing them and I'll only wear the stick-ons, but it's not the same effect. I just find that strapless bras at the end of the day are so uncomfortable. 

Emily: Not only are they uncomfortable, but literally there are times when I take it off at the end of the day and I realize it was doing nothing–it wasn't holding them up, it was just hanging there! It had fallen too low...

Kelly: I have one and it's probably the bra I've had for the longest–I've definitely had it since college–and I don't know why I haven't bought a different one because this one always falls down. 

Caroline: The one that I'm wearing I've had for about 3 years now and it's great. It's the Fine Lines strapless bra; it's pretty comfortable and it doesn't fall down. 

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Leslie: For a really long time, I didn't want to spend money on a strapless bra and then as soon as I did, it felt like the best decision I've ever made. It's funny because it kind of goes against my spending philosophy, which is that you should splurge on the basic things you use every day, since they make the biggest difference. But I just don't care about bras because nobody outside of myself and Jonah is seeing them....

Kelly: How do you think Jonah feels about it though?

Leslie: I've asked him! I'm like "I'm really sorry about the whole I don't wear lingerie thing" and he literally doesn't care. 

Hannah: Yeah, I was going to say as a side note, I don't think it's really about them—I think it's up to you. 

Leslie: Totally. But I also think it is a little bit about him, because if it really mattered to him, I'd compromise and wear lingerie. He's my boyfriend—I want him to see me as sexy, but I feel my sexiest when I'm happy and comfortable, and so does he! 

Emily: More than anything, if it's not something that's making you feel sexy then it's not worth it. I almost feel like we've all been taught from like Cosmopolitan and all these magazines things like "How to do 'X' for your guy"—

Hannah: Right, and I think it's not quite right to dress just for your partner if you don't feel comfortable. 

Emily: Exactly, and the same goes with anything—at the end of the day, I think we can all agree that being comfortable in your own skin is what's most attractive. 

Leslie: But going back to this idea of spending money on something that pretty much nobody sees...

Emily: For me it's always been about hidden confidence and knowing that I have a really sexy set on underneath. No matter what I have on the outside, if I have a great set on underneath, I feel great regardless of whether I've been with someone or not.

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Leslie: And I would agree with that for underwear, but I do want my pieces to be practical for everyday. So I'll wear something that I think is a really great lace design, but it's almost always a nude thong.  

Emily: And I've certainly upgraded my underwear situation to make sure that even the pieces that I want to be really sexy are always comfortable.

Kelly: What is everyone's go-to style of bra or underwear?

Emily: At night, I exclusively sleep in a boyshort and I have two varieties from GAP. One kind is black with just a touch of lace (I wouldn't classify them as sexy) and then the others are also from GAP, and they're blue and white striped and grey and white striped. They are not sexy, they're just comfortable but I hope in a more cute and playful way. Like think Carrie Bradshaw versus just womp-womp. And in terms of daytime, I wear thongs pretty much exclusively and swear by my Natori Feathers bra in nude, even if I'm not wearing white.

Kelly: I only wear a thong when forced, like if I'm wearing an outfit that absolutely demands it. It's just one of those things where I'm not willing to sacrifice the comfort. I wear almost exclusively cotton girl shorts with lace from Victoria's Secret. Has anyone else found that it's really hard to find cute, all cotton underwear?

Caroline: No, because now I only buy Calvin Klein and I only wear cotton.

Emily: So why all cotton?

Caroline: It's more breathable, and it's important for women to wear all cotton underwear to prevent yeast infections. 

Emily: See, this is helpful information!

Kelly: Especially if you work out a lot, it's really important to wear cotton for breathability and to prevent bacteria. And cotton wicks the moisture away.

Emily: So, do you all wear underwear with your workout leggings?

Leslie: Yeah! Wait do you not?

Kelly: Yeah...

Caroline: Yes.

Emily: I do not. 

Kelly: It's two camps, and people are totally in one or the other. 

Leslie: And all this time, I had no idea...

Caroline: I just wear my all cotton underwear that I buy from Calvin Klein in packs of three or five and they're great for workout and every day. They're so comfortable and they hold up so well. And sometimes I'll even size-up so they hit the right place and don't create lines.

Emily: Same! Cutting into my side is the worst.

Kelly: I always size up. And I replace them every year or so because the lace gets holes in it.

Caroline: Exactly! And even if someone sees a peek of them or a bralette, it's not like lacy cheetah print, it's just a classic logo. 

Emily: Which was all the rage when I was in high school. 

Kelly: And it was still that way in my high school too!

Leslie: I forgot to mention! I have one cotton bralette underwear set from Brook There, that I love and it's organic [Leslie wrote about it in Our World last year]. The straps are pink silk so it's really cute, so that's what I'll wear on a Sunday or something.

Hannah: I used to wear the Natori Feathers—I hate padding and there's no padding which is great. I love it and this bra is the only bra that I've ever had and don't want to like immediately take off when I get home, which is saying a lot. And it has thicker straps so never digs in...

Emily: That's important! And it's funny even when we're designing pieces for the clothing line, I'm always aware of things that will need a certain type of bra because I think all those little things make a difference.

Caroline: See, I love a top where the straps are super thin and it's even better if I don't need a bra at all... 

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Kelly: Same! I bought these cropped tank tops from Free People that have such thin straps that I can hide them under other tops. And they provide no support, but I don't really need it! They're great. 

Emily: I wore those in high school to my mom's chagrin...

Hannah: I actually had a conversation with my best friend who looks similar to me but she has an A-cup, so we can share clothes but not tops. We've had the conversation multiple times where she can wear pretty much any top and look good, and then I'll put it on and it will just look way too sexy even if I'm not trying to be sexy or anything. It's so frustrating.

Emily: I remember the fights I'd have with my mom in high school when I would say all my friends were wearing something and my mom kept telling me that my body didn't look like theirs, and it felt like I wasn't even trying and couldn't wear it.

Hannah: It's also just so confusing. I remember as a middle schooler having boobs already and trying to wear what my friends were wearing and feeling weirdly sexualized at a young age. I remember just feeling very weird and uncomfortable in my own body because I felt like I was getting attention that I didn't want and it was a confusing time.

Emily: And even to this day, most people who maybe don't read the blog everyday would have no clue that I have double-D breasts, but anytime that I do wear something a little more revealing—when G and I will go on a date, or something—even just by the end of the night I regret it based on the kind of attention that I get. It's not something that I want. 

Kelly: I feel like this just makes you appreciate the crazy amounts of differences in women's bodies. We're all so different and things will make people feel different in different ways. 

Emily: If you are someone that feels really great about a larger chest and there are like six inches of cleavage, go for it!

Hannah: Yeah, I think it's all about what makes you feel the most comfortable.  

Kelly: Whatever makes you feel good is what you should wear. Society will always have opinions, but everyone should just wear whatever they feel the best in.

Emily: And that's the perfect line to end on!