How To Find The Perfect Bra: A Guide For Beginners & Experts

Most women will agree- a good outfit begins with the right undergarments. It could even be argued that a perfectly fitting bra is the most valuable thing in a woman’s wardrobe. The truth is, however, that most of us are walking around wearing ill-fitting bras without even knowing it. In order to get the scoop on the way a bra should fit, I headed over to Forty Winks in Harvard Square.

Located at 56 JF Kennedy Street in Cambridge MA, Forty Winks is super easy to get to (especially since it's T-accessible!)

The owners, Meredith Donaldson and Rachel Wentworth, two wonderfully fresh-faced entrepreneurs, agreed to sit down with me and discuss something that I could talk about for hours: breasts.

The women opened the shop in April, after realizing that there was a real need for a lingerie shop with a boutique-feel.

“A lot of people our age don’t go to department stores to get fitted, it’s kind of a generational thing,” says Meredith  “Most people will go to Victoria’s secret, but they only go up to a DD, and they don’t carry a 32 DD, which is one of our most common sizes.”

Co-owner Rachel agreed. “I think the common consensus of Victoria’s Secret is it’s really not for women- it was started by a man for men to come in and buy their lady friend things.”

So why do they do so well? Rachel attributes it to their amazing marketing campaigns. In a world run by corporate chains such as Victoria’s Secret and Gap Body that only carry limited sizes, Rachel and Meredith try to cater to all sizes. They currently carry cup sizes between A and H, though they say they are willing to expand if they find the need.

What you can expect when you walk into Forty Winks

“Usually we let customers poke around,” says Rachel. “Though sometimes people come up to the counter and are like, ‘I NEED HELP!’ So, we start asking them questions about what they’re looking for. We usually ask what size they’re wearing, what they don’t like about that bra, if they’re looking for a t-shirt bra, a push-up bra, a lace demi, etc.” From these questions they can usually narrow the selection down to just a few bras, and then it’s time to try them on! According to Rachel and Meredith, it’s almost impossible to have “one-size-fits-all” breasts. Various cuts, styles, shapes, and lines are bound to fit everyone differently. Meredith says that “people are shaped so differently that some bras work really well on some people and not on others. Unless it’s the same line, you can’t really say, well, this is my size.” The most important thing in finding a bra that fits? Trying them on!

Me with Meredith Donaldson, one of the owners of Forty Winks

“We don’t use measuring tape (to determine size),” says Rachel. “We tried it on ourselves and our friends, and really it’s so inaccurate. You just have to try stuff.”

But Rachel and Meredith will definitely be able to help! After many years working in high end boutiques, they’re quite skilled at sizing people up- literally.

“We’ve gotten pretty good at looking at bodies and being like, you’re probably a 34. Most of the time you can kind of tell,” Rachel says.

The biggest issues in the way your bra fits

According to Rachel and Meredith, it’s all about the band. “People come in and are like, I’m a B. It’s not about the cup, it’s about your band. Someone might come in and say, I’m a B, so if you don’t have a 34 B I’ll try a 32 B and a 36 B…but it’s not about your cup size it’s about your band. It’s not the same…if you’re a 34 B, you should try a 32 C or a 36 A. Find a band size that fits you, and just adjust the cup.” This was definitely news to me! In fact, according to Meredith and Rachel, I’ve been wearing the wrong band size for years! Bra shopping has always been a challenge for me, since I’m a fairly curvy girl. And yes, there are absolutely bras out there that provide the right amount of support for women with large breasts, but they aren’t exactly fashionable. When I presented my dilemma to the ladies of Forty Winks, they managed to help me find my literal dream bra. Although at $88, it was a little bit out of my price range, I ended up buying the Chantelle Rive-Gauche 3-Part Cup bra, and nothing has ever fit me better! It is super comfortable, supportive, and gorgeous. Rachel and Meredith even gave me some tips to keep my bra looking good and fitting properly for as long as possible. They say you should never put your lingerie through the washing machine. Instead, soak it in the sink in an alcohol-free detergent (they recommend Soak Wash), and hang it up to dry.

Chantelle Chantilly Sexy Demi bra and Sexy Shortie for $98 and $44

After a lovely afternoon with these ladies, they left me with some very important tips for knowing when a bra fits.

  • Make sure the band fits snugly on the loosest hook when you buy the bra, since it will stretch, and you may need to tighten it (unless you’re early in pregnancy, in which case you should buy a bra that fits snugly on the tightest hook, as you will need to make it looser).
  • The fabric in between the cups should tack against your sternum.
  • You shouldn’t be spilling over the cups. If you want some “poppage”, it should be in and up, not over.
  • If the straps are falling off, it’s usually a sign that your band is too big.
  • Don’t shop for bras during your period, as many women’s breasts experience changes in size and texture. Instead, opt to go lingerie shopping the week after you finish menstruating.

Cosabella Airelace Underwire Bra and Airelace Boy short for $66 and $26

Last but not least, Rachel and Meredith gave me some recommendations on various lingerie lines.

If you have…

  • Breasts that sit a bit farther apart, try Cosabella, as their cups are much wider-set.
  • Small to medium sized breasts, try OnGossamer, as they run from A-DD.
  • Small to large sized breasts, Chantelle and LeMystere seem to run the gamut (they go up to a J cup; Forty Winks carries up to an H).

So if you’re ever in the Boston area and are looking for a refreshing lingerie shopping experience, definitely stop by Forty Winks in Harvard Square. Until then, in your own bra-shopping excursions, remember to try try try! Don’t give up on finding a bra that fits you, because I promise you, it’s out there somewhere.

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About Michaela


Michaela is a recent Seven Sisters graduate with a self-designed degree in Sexuality Studies. When she's not blogging, you'll find her teaching Health and Wellness and A Cappella to high school students, helping women find properly fitting bras, and working as an editor on a documentary. She hopes to continue her education one day with a PhD in Feminist Anthropology.

  • Laura

    Wow! This is great information! I wish there was a shop like this in my area. Have you guys thought about putting a list of lingere shops that offer great service like this together?

  • Billz

    I appreciate the effort that you put into this story. Perhaps they can work on men’s briefs that provide the same results.

  • Kate McCombs

    This was a wonderful post, Michaela. I have spent many hours struggling to find good bras/swimsuits and recently I found a website called that specializes in unusual bra sizes. I found a perfect swimsuit there. They do free returns/exchanges within Australia, but I got lucky the first time around. Interestingly, I’ve found that England is the easiest country to find unusual bras sizes. The department store Marks and Spencer (which is in nearly every city in the UK) specializes in bra fittings. Maybe English girls have larger breasts?

  • Michaela

    That’s good to know, Kate! As a 34 F myself, I know it’s definitely hard to find properly fitting bras. I’ll check out the website!

  • Debby Herbenick

    Agreed, Michaela. Excellent job! I hope to visit Forty Winks next time I’m in Boston. Thanks for bringing such a lovely and helpful shop to our attention.

  • Debby Herbenick

    It would probably be tricky for us to identify such a list, but hopefully readers will let us know what’s in their area and maybe we can arrange for more profiles! We’ll keep our eyes peeled as well. I’d love to learn about lingerie stores like this in Indianapolis, Denver and Las Vegas – all cities I’ll be in over the next few months – as I’d be happy to arrange a visit.

  • Holly Moyseenko Kossover

    Great article! Thank you for this great interview and some good tips. I walked into a lingerie store about two years ago and had a (very nice!) sales associate quickly tell me that I was wearing the wrong size bra and hustle me into a fitting room with some new bras to check out. She was right! New bras procured, I looked like I’d lost a few pounds and my shoulders didn’t hurt as bad. Now if they would please open up a store in Cleveland…