Penelope's is a cool alternative to mass produced clothing stores like the Gap or Urban Outfitter's. They predominantly sell women's clothing, but also have some choice stuff for men. They sell jewelry made by local crafters. They also sell Lomo cameras and Freitag bags as well. The clothing here is top notch; stuff that I would love to be able to wear, but that is where my complaint lies. I am a Size 16 and it has been nearly impossible to find anything there that fits me. It's disheartening that many of the boutiques, especially independent ones, don't cater to the average sized woman. read more

Lots of cute crafty t-shirts and odds and ends that will make anyone who wears their personality on their chest delighted. As soon as I lose a few decades, gain several inches in height, and decide that I want to look like everyone else in the neighborhood, I'll start shopping here. read more

This is a place for very fashion concious people who must have just the right piece for just the right event. Very casual stuff, very cute, very young oriented. My gils found it wonderful, but Dad has no money! Ugh! read more

My only gripe: It bugs me a bit when I get an adorable, perfect, quirky, fun t-shirt here and find it in the Delias's Catalogue two months later for two dollars cheaper, but that is the only bad thing I can say! Great shoes from Pink Studio and Dolce Vita (Two of my favorite labels) and lovely, well made, soft, unique clothing items from a variety of smaller, more independent, middle end designers. They don't state anything in this regard, but I swear, soft clothing has to be a specialty! I am especially fond of Moss Mills tops and jewelry. I can always find a few small, unusual, well made items after which I completely lust. I can browse here forever and the employees don't seem to mind. Their packaging is SOO cute too! I have a nice little stack of strawberry stamped bags and little jewelry boxes I keep around to recycle on gifts. Minus one star for only carrying a few of each item (snatch them up FAST!) and for rarely having skirts or pants that fit my bottom half. Also, I don't mind the pugs at Paperdoll, but it does bug me a bit when I buy a new item and have to lint-roll off someone else's pet hair . Hmm, I guess the t-shirt thing is not my ONLY gripe. read more

awesome store, but not much in skirts/pants for a 5'2" size 10. great shoes, tshirts, bags and accessories. cute puppies that snore are always a plus. read more

This was one of those stores where I knew that if was a million dollars richer, 2 bra cup sizes smaller and 50 lbs skinnier, I'd buy everything that they have for my wardrobe. read more

Probably the best boutique in town. Not only do the have a wide variety of prices to accommodate a myriad of shoppers, but they have the latest in French street fashion with labels such as Sessun and APC. The staff is amazingly friendly and not obnoxiously helpful. They emailed me when the new spring 09 Sessun line came. The sales are great. Other boutiques around the city carry the standard few lines that are ubiquitous in the United States and its nice to fine a boutique that carries unique finds that are not all made in China (why I won't buy a Marc Marc Jacobs dress ever again.) I shop at a boutique to find unique clothing and not to look like a j crew catalog. read more

Oh i like this place. It's a casual modern look for females of all ages. I think that they have men's clothes too - but I was much too distracted. I saw plenty of middle-aged and young ladies shopping here, and the clothes looked great on all of them. I saw the same name brand items at other stores costing almost twice as much. I think I'm just so estatic about this place because I found the down winter jacket that I've been looking for! I wanted one that was at least knee length to deal with the winter, but I wanted it to be fitted or to have some type of feminine shape to it. It also has a hoodie. It's a beautiful green. I am actually anxious for it to be cold enough so I can wear it. I can't even believe I'm saying that considering how much I hate snow. The staff there is really helpful. She helped me find other colors and styles of the jacket, and the price was around my budget. I think I might go back and get a thermal shirt there. read more

Nice store, nice set up, pretty low key...I found a natural product here that I'd seen on Instagram that I didn't know was sold in select stores. For that I'd drive back to Penelope's! And I'm pretty sure I will be back to re-purchase when this product runs out. Although my eyes spied very nice clothing, it was a little expensive for my budget, but a girl can look, right?! read more

Reading the reviews, I guess I'm not the only person hesitant to walk in, though I think it has more to do with the prices than the staff, who have usually been pleasant enough and hands-off. The price hike makes me sad, b/c when I first moved here a few years ago, I could definitely afford to splurge (and by splurge, I mean even considering buying anything) more often. Now, I don't even bother looking, unless the big red Sale letters are in the windows. Still cheaper than New York...but Chicago ain't New York. read more

I adore this shop, I feel like I've grown up with it since I began shopping there in my mid twenties. They have introduced me to some amazing brands (please don't ever stop carrying Des Petits Hauts!). The price points are cross a spectrum, so when I'm feeling less flush, I can go in there without too many worries--plus there is usually a great sale selection. Finally, there is a nice balance between more classic styles and trendy pieces. read more

the only thing i will say: do not leave work early on a friday, go have a few drinks with a friend, and then tell each other that "we should just stop in and take a peek." i want to live in this store. read more

This store has been putting me in great clothes for over ten years. I call Penelope's "my personal shopper" - it always has a well-culled collection of great pieces and I always find something I love. While the online store only has a limited selection, the location on Division is well-stocked with lots of rotating merchandise. Thanks, Penelope's, for dressing me through my 20s and 30s! read more

Nice selection of clothes, especially the dresses-reminds me of Francesca's but the quality is better and of course more pricey. I didn't have much time to browse further, but can definitely see myself coming back. read more

The reason to go to an independently owned shop, as opposed to Target or H&M is precisely because it is independently owned and ostensibly carries unique items. I like saving a buck as much as the next person and yes, Penelope's does charge more than those stores mentioned above. But I also like to occasionally wear something that not everybody already has. Anyway, I stopped in last Sunday and was really favorably impressed with the selection and the attitudes of the sales people. It was laid back and they seemed to really appreciate the business. Also, having lived in Denver for the last 10 years, I can tell you that not every city has places like this to buy from. In Denver, it's often Macy's, Anthropologie or Target. Not much in between! read more

One of my favorite boutiques in Chicago! APC clothes and Baggu pouches and tons of cute loafers!! Men's, women's and babies apparel, you will find something for everybody . read more

I do most of my shopping either online or at second hand stores and my one exception is Penelope's. I love, love, love this place. I love the adorable sweet hearts that work here, I love the pugs, I love the products. I always come in and end up spending a fortune, but I never regret it. There are some good deals too! I've purchased awesome several t-shirts there in the $20-$30 dollar range. I always stop here when I want to spoil myself, and really all my favorite "new" clothes are from here! ;) read more

I stumbled on Penelope's by chance when I was browsing for a pair of Rachel Comey boots online and found not only a great deal but that the shop was basically in my backyard so I could pick them up in person instead of waiting for them to ship. I came in close to closing time to pick up my online order and wanted to browse the selection. Sofia didn't make me feel rushed, and was really knowledgeable about the lines they carry and how the different brands fit. They carry a fantastic selection of European brands - A.P.C., Sessun, Won Hundred - as well as American-made lines, including a good variety of outerwear. There's definitely much more in the store than what's listed online, but it's all well-curated so the selection isn't overwhelming. I loved the layout of the store and the mix of classic, minimal, and statement pieces, which reminded me of Steven Alan or Colette. Definitely worth a stop if you're looking for a staple piece or something special. read more

Love love love this store! The staff is always helpful and nice, and the clothes they have for both men and women are amazing. If I could afford to have my whole wardrobe from here I would. read more

My favorite apparel store in the city! I'm a graphic designer so I like a little style but nothing too trendy and don't have to wear the traditional "office attire" so this shop is perfect for my taste. Love that they source from USA made brands as well, as I try to avoid fast fashion as much as possible. read more

Expensive clothes, but I believe lots are also locally made one-of-a kind type things so that's cool, I guess. If you've got a lot of cash to blow, or your parents gave you a credit card, maybe stop in here. You'll definitely find something you like... read more

This place is so fun. First- the dogs? So cute. There are so many gift items for someone and yourself! Quit complaingin about "price" -let's support local business (especially ones with great imaginative style!) read more

An amazing store. Great selection of curated clothing and accessories. Love that they carry handmade shoes from Peru and a good selection of pretty much anything for the fashionista or just the casual, well dressed mom or dad. read more

If I could afford it, I would shop here more often. I am pretty frugal with my money, but I try my best to buy for quality while supporting local, small businesses, and Penelope's has been a good bet for finding something I'll keep for a long time. The style is or close to what I like. The problem is that I rarely have the nerve to go shopping, and when I do, I am very picky. The last time I bought something it was a pair of shoes for my boyfriend that were on extra special clearance or whatever so there are totally deals to be had. Before that, I picked up an APC dress for my birthday that hasn't yet cycled out of my wardrobe. So that's maybe two things in a year. I browse more than buy, and everyone's been really nice to me here even if I'm just poking around. Sometimes, someone will engage me in a light chat, but customer service here is relatively hands off. Great. I don't really need anyone to dote on me while I browse. I like that a lot of the clothing I ogle at on the internet can be found here. I know I won't be able to find certain things in this lovely city other than at Penelope's, so I'm glad they exist. read more

Cute clothing but it's way overpriced. I'm a designer and would never dream of charging $360 for a dress. Stupid.

I am way too (a) old and (b) stout to shop here myself, but I shop here for my EXTREMELY tall and skinny husband who has almost no clothing options. The store is definitely trendy, and some things are clearly overpriced. However, other items, like men's dress shirts, really aren't. If you are the kind of guy who knows the frustration of trying to find XS shirts or 28" x 34" jeans, this is the place for you. You may have to search to find anything simple enough to wear to a semi-professional job, but when you find it, chances are they will have it in your size. read more

This is a really great store on Division. They have great clothing by Grey Ant and American Apparel and others. They also have some cool accessories. I love checking out the art books they have and the cool notebooks from UK label Sukie. read more

I just moved here and this is pretty much the only store I've been to that I like and would make an effort to return to. The staff has been consistently awesome - friendly, helpful, unobtrusive - including the 2 cute pugs that run around the store. I don't know a lot about fashion, especially small boutique labels, all I know is that I wanted to buy almost everything in the store. They had the cutest bags and trinkets. I've already shopped there a couple times, got a good deal on sale things, and my BF got a nice coat which was under $200. I don't give it 5 stars because the coat that my BF bought, well, when we got home we noticed all the buttons were ready to fall off. It wasn't a huge deal, just sewed 'em back on. Compared to the other little shops in the area, this one is by far the most interesting, varied, and welcoming. read more

Penelope's is adorable. It's just the way boutique shopping should be. The clothes are beautiful and high quality, the salespeople are sweet and helpful, and everything is displayed in a way that is not only beautiful, but practical. I didn't get to see the pugs, but they could only make something good that much better. read more

Penelope's is a bit on the pricey side but I just LOVE everything in the store; super cute and unique clothes. It's always nice to find something that not everyone else will be wearing. Also a great place to pick up wardrobe staples; LAmade items aplenty...they make a great cotton shirt. read more

I used to live across the street so I spent a lot of time perusing through this store. They have a great selection and chances are you won't run into anyone on the street with the same outfit on unless they are either bigger or smaller than you which is a huge plus in my book. Their prices are also very reasonable especially for being a boutique. Although some pieces may be pricey to some make sure to check out the sales section where you can find some really great bargains. read more

I love this store, it's maybe my favorite in Chicago. The cuts in the clothes are very very flattering. At first, I wondered why the prices were a little high but then I tried some clothes on and I can totally see why. The garments I have purchased from this place definitely get the most mileage. I am totally in love. I wish they were closer to my house, but maybe it's a good thing I'm not able to go there every day :) read more

This is a cute boutique in Wicker Park that is worth checking out. The prices are high, but the products are cool and different.

Very unique trinkets here. From apparel to home, Penelope's stocks hard to find items. A great place to find a gift for the home.

Penelope's would, at first glance, seem like the kind of place where you'd want to blow your entire paycheck. The problem is, you realize that you don't really need everything here, and you would need like three paychecks to buy a bag full of merchandise. Did this place hike their prices recently? It seems like it. Still, the things on sale are pretty cute and hip, and you can sometimes find a decent deal on something. Aside from clothes, Penelope's offers a small array of accessories and paper goods. read more

If I could afford it, I would buy everything in the store. I love mostly everthing there...unfortunately I rarely buy clothes here because I can't afford to. Minus 1 star because of the prices. read more

Nice quality clothes, very modern. The service was excellent, if not perfect. I bought some blue shorts - I think the prices are a wee bit high - but would definitely recommend it if that's not an issue. read more

This store has super cute items from clothes, shoes to trinkets for your home. But some items I think are a bit overpriced but I have made a few purchases here along with many times just browsing. The staff is friendly and willing to help, just wish it was a bit cheaper and I am no cheap ass... read more

I bought my Spiewak jacket here, as well as three Frietag bags. The staff is really friendly and helpful. They did some digging for a Spiewak item I wanted. The dogs are cute. It is hipster, for sure, but I am okay with that. They should however, order more +10 sizes, and, yes, they are pricey. I would like to see a resale rack, where everything is 10-20$. Moreover, they could have layaway. Consider it, Penelope's. Thanks!! read more

This boutique is really cute!! They have really nice pieces, which are obviously more expensive, but they also have affordable lines like tulle (which is also sold in nordstrom stores). It's a great mix between essentials, basics and some fun printed dresses and tops. They also sell shoes and bags above and below their racks of clothes. I noticed that they had a guy side which was pretty proportionate to the girl's side, which I feel is hard to do. I wasn't able to find anything that I loved the day I went (plus the several items I loved, I couldn't splurge on), but I'm determined to go again and find a gem! read more