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Reader Question: How do I tell someone they might be wearing the wrongsize?

Over the weekend, a reader emailed me with a great question. Take a gander below at what Anonymous asked:

I'm a guy, but my girlfriend is a 34dd (so she says), and I was hoping you might have a suggestion.  I always tell her that her bras just don't fit her - she looks like she is falling out of them in the front, and the back just seems loose.  She did get measured at VS, and they said 34dd like 5 years ago, so she has always gone with that size.  We have only been dating 6 months, so I don't want to insult her by pushing it, but I feel like I should just buy her another size, like a 32 something, but not sure the best way to approach it without insulting her.  Any thoughts?  Thanks in advance.

My first reaction was, "Grrr! Victoria's Secret, you machine of lingerie failure! Curse you, behemoth of full bust despair!". Then, I realized how delicate this topic is and how many of my readers might be struggling with it in their own lives. I'd love to read your reactions in the comments and I'm sure Anonymous would appreciate them too. Here are my ideas:

Sensitivity and respect are essential.

Once, I cut off all my hair for fun. When my boyfriend-at-the-time saw my new pixie locks, he told me it was the worst thing I could've done with my hair and he would have a difficult time being "romantic" with me because now I resembled his middle aged mom. Last spring, I died half my hair platinum blonde and I looked straight-up cray. Mr. Underpinnings told me I'd look beautiful no matter what and that it'd be easy to fix, if I wanted to. In any conversation about a woman's body, sensitivity and respect are key.

Bad hair cuts & ill-fitting bras: Boyfriends, be gentle!

                                        Bad hair cuts & ill fitting bras: Boyfriends, be gentle.

More specifically, a dialogue about bra size can be fraught with implications and insecurities. Remember, her breasts are inherently tied to her self image, sexuality, and physical confidence. When you discuss their size, be aware that you won't simply be talking about a number letter combination. It pays to be as subtle, complimentary, and as gently honest as possible. It's also wise to keep in mind that it's her body. She might not want to wear the "right" size. It sounds crazy to some people, but many women consciously choose to wear an ill fitting bra or prefer to upsize in the band while downsizing in the cup.

Caution: Random Sizing Ahead.

I wouldn't recommend buying her another size. When I first went off the college, my mom actually tried this with me. Bless her heart. She knew my bras looked weird so she ordered a bunch of Title Nine bras in various sizes. Unfortunately, jumping from a 34DD Victoria's Secret bra to a 32E Title Nine didn't do a world of difference. I was still left falling out, sagging, and generally looking like a hot mess. If your girlfriend is really a 28F or a 30H, one band smaller won't improve her fit problems significantly. Your best option is a professionally trained fitter who can give her a world of size options.
Point her in the direction of the experts.

At the store, we have supportive husbands, boyfriends, and family members come in all the time to buy their ladies gift cards. We hear how these women "desperately need new bras" or "will definitely need a fitting". It's not unusual to notice that your female friend is wearing the wrong size or that her old bras are dead. We like to joke that these extreme cases are "bra interventions" and (I can't stress this enough!) they happen all the time.  If you live near a lingerie boutique or fitting department, I'd suggest taking your girlfriend there. It's a cool date idea! She'd probably appreciate the moral support too. If you aren't located within a reasonable driving distance of a consultant, I would recommend either the excellent size calculator on The Sophisticated Pair's website or the Skype fitting sessions with Claire from the Butterfly Collection. There are fantastic resources out there and she might just need a small hint as to where they might be.

What do you think of Anonymous' dilemma? Have you ever told someone that you think they might be wearing the wrong size? How did it go? Has any family member/boyfriend/friend told you that they think your bras didn't fit you?

15 Comments

  1. My first thought was: This is the best boyfriend! :-)

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  2. Try telling your GF you want to buy something special for her and then measure her. If she asks why your measuring just say that it's European, British, or Australian sizing. Then just buy something special online in that size. It might not be exactly the right size, because measurement is just a starting point. But at least she will be able to see where she is going wrong.

    Brastop.com, Bravissimo.com and Figleaves.com offers some great styles for D+

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  3. One time I went bra shopping with a friend. She is about a "34C." We were at everyone's favorite store: Victoria' Secret. She tried on a bra that was really cute for her, but the cups were too small. I told her to try on the D. She said "NO WAY I AM A D CUP THAT'S HUGE."

    She left without getting the really cute bra.

    I am a little worried for her. She is nursing right now and easily a DD at the moment. Maybe more. I think soon she might have to come to terms with being a D. Or more.

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  4. Being blunt has always served me best, but then again most of the people I know aren't oversensitive and over-estrogened(?). If I was the guy, I wouldn't tell the girl about the blogs because if she checks them out, she (I'm assuming she's insecure) may be like, "What are you doing looking at tits all day?!" Haha. Oh and by the way, the US army sports bra options are abysmal. They only come in S, M, L, XL!!! Seriously, funding for one bomb could buy correctly fitted sports bras for all the women that serve our country.

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  5. K-Line, I had the same thought! I wish I'd had such a boyfriend years ago, so I could've been wearing the correct size bra all along.

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  6. What a nice boyfriend!

    I think a lingerie boutique with a good professional fitter is the way to go.

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  7. Gift certificate to a reputable lingerie boutique that specializes in fittings sounds like it'd be ideal. Hope there's one near him!

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  8. Say you want to treat her to some lingerie, if you don't have a good shop locally then from figkleaves ( other sites are available) and lead her to the fitting/size page - tell her the fittings are different from VS and work from there on - Bravissimo might be a bit of shock.!

    What a thoughtful man you are

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  9. Steve (former anonymous)June 13, 2012 at 2:22 PM

    Thanks everyone for all the advice - I'm still debating the best approach, I will let you know how it turns out!

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  10. If you're close with someone, sometimes it's best to just be blunt. No need to be rude, of course. But try something like: "You have a great chest and your bras aren't doing it justice. Have you thought about getting a fitting at [name of a store with good fitters]?"

    When I was wearing the wrong size, I thought my breasts were wrong... as it turns out, it's generally the bra that's "wrong". It might help to show her some blogs of D+ women. I just wrote about how a lot of people think that D+ cups are huge when, in reality, they aren't huge at all. Seeing a) what D+ sizes look like and b) what a well-fitting bra looks like might be enough to convince your girlfriend that she needs a new size!

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  11. I agree! I think awareness and understanding of what these sizes look like is key. A D-cup isn't huge, but for whatever reason, it's taken on this epic connotation. It's tragic too, how many women blame themselves or their bodies when bras don't fit right.

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  12. Thank you for mentioning us! It's a really tough prospect to tell someone you think they're in the wrong bra size, especially if they aren't sure how bra and cup sizing works. I had a gentlemen call the other day who wanted to know if he and his girlfriend could come up for a fitting and to look at the lingerie. It can be an great date opportunity, as you mentioned, and the woman will leave feeling fantastic about herself.

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  13. Of course, Erica! I love that your fitting calculator takes into account personal preferences about the product. Fittings don't come down to just a numbers game and I love that your online resources take that into account.

    I totally second the date perspective. It deepens intimacy and it's sexy. Win win.

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  14. Taking her to lingerie boutique that sells a full range of sizes and offering to buy her something seems like the easiest solution. But it sure does make it hard when those boutiques are hard to find the US.

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  15. [...] “More specifically, a dialogue about bra size can be fraught with implications and insecurities. Remember, her breasts are inherently tied to her self image, sexuality, and physical confidence. When you discuss their size, be aware that you won’t simply be talking about a number letter combination. It pays to be as subtle, complimentary, and as gently honest as possible.” Reader Question: How do I tell someone they might be wearing the wrong size? – miss underpinni... [...]

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