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Pinching underwire, tight bands, the dreaded spillover from a too-small cup--there’s so much that can go wrong when it comes to choosing and wearing a bra. Lucky for you, we see well-fitted, comfortable undergarments in your immediate future. These five lingerie shops will have you feeling your best in no time.

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: Rigby & Peller/Yelp

Rigby & Peller

Prepare for a bra-fitting unlike any other. At Rigby & Peller, they do away with the tape measure and simply look at you--yes, they do recommend you go topless--so they can select a garment that is perfectly suited to the curves of your body. The expert stylists at the store will also give you a lesson in how bras should fit and how often you should be replacing them (hint: way, way more than you probably do).

900 N. Michigan; 312-337-8366 or

Bras Galore/Yelp

Bras Galore

We absolutely love this shop quietly tucked away on Lincoln Avenue. You fill out a questionnaire the moment you walk in so the stylists can understand what you do and don’t like in a bra before you even get measured. The store stocks a wide, diverse selection of undergarment brands, and the stylists will stay with you every step of the way until you’ve found the perfect fit.

3148 N. Lincoln Ave.; 773-697-9199 or


La Perla

Super sexy and super comfortable don’t have to be mutually exclusive. Head over to the Chicago outpost of renowned Italian lingerie house La Perla to find the bra that makes you feel like your absolute hottest self. Not only are these bras made with care, but they also have the sort of flourishes to make you forget you’re wearing an actual undergarment. 

34 E. Oak St.; 312-494-0400 or



At Underthings, the stylists take care of everything for you. The inventory is located in the back of the store, so you don’t even see bras that don’t at least have the potential to perk you up. You’ll love the one-on-one attention--this is the place to go to ask all those questions about bras that you’ve never really gotten straight answers on. One of the best tips we’ve learned? Don’t wear bras more than two days in a row. You’ve got to give the elastic a rest if you want it to stay strong through the long haul.

804 W. Webster Ave.; 773-472-9291


G Boutique

This is so much more than just a bra shop. It’s a haven for all things super sexy, including bras, wedding lingerie and, yep, sex toys. The store associates are knowledgeable about all of the above. That’s the kind of support we need.

2064 N. Damen Ave.; 773-235-1234 or

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