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Chicago, IL

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Wear Lively

5.0 (5 reviews)

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Underthings - Bra and Panty sets galore

Underthings

4.5(58 reviews)
0.3 mi•Lincoln Park, Sheffield Neighbors, DePaul
•$$

Maria, the owner, knows her stuff! I'm 49 and she was able to fit me correctly into a bra for the…read morefirst time in my life. She asked what I was looking for and gave me a large selection to choose from. I was buying items for a boudoir photo shoot, so she had plenty of suggestions. Aside from being incredibly friendly and helpful, it was comforting to know that I was in good hands!

I think I have visited most of the small businesses in the 'burbs that cater to "what lies…read morebeneath," as it were. I've given up on department stores for finding my size, and it's just easier to have someone who knows what they're doing spend some time with you. Yeah, they're usually more expensive, but you wear these things all day every day. So I am of the "throw some money at the problem" school -- invest in some proper basics and you won't keep re-buying for a while. Given that framework, while in Chicago one week-end a girlfriend indulged me and we went on a mission. This store is small but laid out with loving attention, and everything is beautiful: matched sets along one wall, a glass display table in the middle, an array of fluffy maribou slippers in one corner. This is a place where you ARE at the mercy of the clerk who is helping you, because the stock is in the back. She'll measure you [this really is vital, no matter where you shop. YOU are never going to "guess" right!] and then start running back and forth to find you styles based on what you are saying works and what doesn't. It took a few minutes for the young lady and I to get in synch; she was a bit brusque at first, but when I explained what problems I was having (and the problems I TYPICALLY have), that seemed to help and everyone mellowed out. She knew everything about the brands, which came with sets (one bra I bought was part of a set that even had a garter belt. Woo), and didn't seem judgy when I told her that a couple were out of my price range. I ended up with several things and have been very happy with them! And thus my lingerie boutique addiction continues. I don't live close by, but I am in the city often enough that the next time I need an infusion of underthings I can easily enough come in. Definitely worth the trip.

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Busted Bra Shop - Bras Galore carries bands 28-46 and cups A-P.

Busted Bra Shop

4.4(151 reviews)
1.7 mi•Lakeview
•$$

First of all, I haven't been bra shopping in awhile. It's always a harrowing experience being a…read morethicker woman. I'm always faffing about with what I'm sure is the wrong size and finally just being frustrated but buying it because mama needs a bra. This is place is for someone serious about getting a quality piece of (dare I say it) comfortable yet supportive (and perhaps a little sexy) undergarment. Now I will preface this by saying I haven't bought an underwire bra in a long time. I always felt like those 2 pieces of metal were slowly deforming my rib cage, ala eighteen century Victorian torture corsets. This is not the kind of bra they sell here. I've never felt so comfortable in an underwire. I'm a tee shirt bra/sports bra kind of gal. But I had a dress that required something a little more supportive, yet displayed the girls to their fullest advantage. My consultant was BJ. What an absolute gem of a professional. First she took my measurements and once we ascertained my size, she helped me actually put the bra on, nipping and tucking where necessary. After that we chatted about what I was actually needing in this visit. She didn't try to sell me 8 bras, I really only needed one. But she brought me different styles, price points, and aesthetics. I bought one of the pricier pieces because of how absolutely lovely it was...delicate, supportive and with sexy elements. I think I feel more sexy when I have a risqué piece under a rather sedate ensemble. Aldo when I say privy, probably only $15 more than a bra normally costs for me ($79 vs $65 ). The service here is perfection. If I was looking for undergarments for my wedding this would be the place I'd go. They taylor the experience to your needs, which they ascertain without you being explicit, even if you don't know what you need. I bought some thigh highs that they had in my size. They carry bathing suits year round. I was buying a black bra so it was in stock but they have an online platform that carries all their styles across their different stores (BJ told be each one has a different vibe, so that's cool). I'm thrilled to have found this kind of store. They have a reasonable return policy, and a more than adequate supply of perfect pieces. Give them a shot. You are totally worth it.

Maggie was such an amazing help! She was knowledgeable, kind and had great attitude. She was…read morerespectful and made me feel uncomfortable throughout the whole fitting and process of finding a bra!

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Busted Bra Shop - Low impact and high impact sports bras. Petite sports bras, full bust sports bras, plus size sports bras, sports tank with built-in bra

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Early to Bed

Early to Bed

4.7(165 reviews)
4.1 mi•Andersonville, Ravenswood, Uptown
•$

This was our first time going into Early to Bed. The store itself always gives me a tickle on the…read moreoccasions The Doctor, The Queen and I have seen people go into the store, only to run out...HAHAHAHAHAHA! Guessing the name may have led them to think that it was a bed linen store. Anyway me and The Queen popped in there after leaving The Hopleaf as we saw a make shift sign on their door advertising a flea marker, so we decided to pop in to see what was going on. As it was my first time in the store, I can say it is well organize and they seem to have something for everyone for the most part. The overall vibe is chill and light, and the staff was friendly. I was not even aware that the store had a back area, so we were directed through a door and saw several vendors selling their products. There was a mixture of items being sold, from panties to stickers. I ended up purchasing two very cute purses and some stickers to pass out to some of my co-workers who are high performers who are not being appreciated that simply stated "You deserve more than survival", which they loved as it made them pause and think about what their value was. The prices were not too crazy and the two purses I got were well made. Again going back to the vibe of the store, it is very welcoming and feels safe from judgment. Me personally, I felt like this would be a store to come to for recommendations and questions it you were unsure of what you were looking for. And now that I know they have these market days, I am going to keep an eye out for that to see if there are any more cute purses I can purchase.

Early to bed is such a fun place to stop in Chicago! The staff made a very relaxed atmosphere and…read moreare very welcoming. I was really impressed by the variety of inclusive toys, not just cis and straight focused. And I also loved the mixing in of non-intimate items that are fun and cute to look at! I have a loyalty card and definitely coming back!

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PURE Boudoir - One of the photos, straight from the camera.  No editing needed!!!

PURE Boudoir

4.8(25 reviews)
2.2 mi•Fulton Market, West Loop, Near West Side

I have done my bridal boudoir photos and maternity boudoir photos with Pure Boudoir and it has been…read morean amazing experience each time. Magdalena makes you feel so comfortable and directs you on how to look your best. I was nervous taking my maternity photos because I felt larger, but she helped me pose so that every picture turned out beautifully. My husband was also there for maternity photos and Magdalena worked well with the both of us and the pictures turned out gorgeous. The products are also so high quality. I ordered an album and it was flawless. I can't recommend Pure Boudoir enough!

I booked a boudoir session with Magdalena to get some photos as a wedding present for my fiancé…read more Before the session, Magdalena sent detailed instructions on what to expect and how to prepare. The morning of the session I had also booked hair and makeup through someone she recommended, and their services were great! The session itself was also wonderful. Despite the fact that I had never done something along the lines of boudoir before, Magdalena gave a lot of instruction on how to pose and ensure my facial expressions also conveyed the right tone. She stopped to show me photos along to way so i could see how they were turning out. She promptly shared the unedited proofs with me, and they were all so good it was so hard to decide which ones I liked the best! If you are considering doing a boudoir shoot, do not hesitate to book with Pure Boudoir!

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Wear Lively - lingerie - Updated October 2026

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