Penelope's

Another fun boutique and gift shop. Women and baby clothing, hair accessories, earrings, jewelry, homewares, decor, purses, greeting cards, candles, and more. There are fitting rooms and there was a cute dog. The adult clothing is sorted by color which is aesthetic. Plenty of fun things at which to look.

1/2 of Chicago’s best clothing retailers (The other being Gemini). Tasteful. Quality. Vibes.

*Update* I’m pretty happy to say that the GM of Penelope’s contacted me to rectify the situation below. I’m all about uplifting small businesses that make things right. 5 stars for quality clothes, and a business that cares about its customers. I’ve spent a good amount of money at Penelope’s, but unfortunately I’ll have to find a new shop. I purchased a pair of $70 shorts 9 days ago, but ultimately I decided they weren’t for me (Didn’t wear them outside of trying them on/brought them back in perfect condition). I took the pesky tag off when trying them on, and tossed the tag. I thought to myself, well I have the digital receipt from them, so I should be able to return them still…. I was wrong. I was denied a refund because the tag was gone, and I guess they can’t print a new one, or make a makeshift tag in this scenario…. (thinking to myself, what happens when a tag accidentally gets ripped off in their dressing rooms, do they lose money because they can’t sell the piece anymore?) Anywho, I was verbally told that in order to receive a refund I must have a tag despite having a legitimate receipt and being back within 21 days. A loss is a loss at the end of the day, but I just wish that either the cashier would explain the return policy at checkout to customers, or the policy would be printed on the digital receipt/email. Instead, I had to find the policy out from the sales associate when I came back to this side of town, or just know to check their website. All in all bummer of an experience.

I felt flattered and beautiful wearing this casual dress I brought here in Penelope’s. I love this boutique especially since their have a wide variety of fashion and trendy clothes to choose from. They have clothes both for men and women. They also have formal clothes which are really of high quality. The items here are a bit pricey since they also offer items from high end clothing lines, but everything is worth spending money on because of its high quality and design. They also have a welcoming and friendly customer service. I loved that the items in this store are well organized and the surrounding is clean. Did I mention that they also offer items for children? This boutique is perfect for people of all ages!

I love browsing this boutique and not having anyone bother me. Sometimes I like what I see, and sometimes it’s boring.

Since the first time I saw the dress that my sister had purchased from this shop, I've had a strong desire to pay this boutique a visit. I really liked the dress that she wore to the party that we went to together. That is why, I insisted that she come with me to this store and assist me in selecting the dress that will look the most flattering on me. And I am so grateful that we were able to find one; it is of such refined quality for me. I gave it a shot once while out on a date, and both me and my partner liked it. I cannot express how grateful I am that I was able to find this store. Absolutely worth every penny. I will definitely recommend this store to my friend. This is the kind of boutique that every customer will really adore.

I came to this place and one of the staff greeted me. I look at their products. I can see some boxes on the floor. They should put it in the right place to prevent tripping hazards. There are only a few products I can see. Their products are cheaper and more expensive one. I came here to buy my husband a polo shirt. And I found a blue and white polo. My husband has a lot of white polo in his closet so I chose blue. It was thick and not too hot to wear. I think it will fit my husband since I know his size. I went to the counter to pay for it. The staff were too slow to prepare my purchase. She was busy talking to someone on the call. She should prioritize the customer first before calling or while calling. This place should improve.

I like the men's collection of this store. The clothes definitely have a great quality and design. Most of them comes from a good brand and there are various casual and formal selection. That goes the same with their women's selection. The store is a typical boutique and it has a designated location just around the other stores in the area. It is clean and everything is well organized plus their staff are warm and accommodating. When it comes to the pricing, all of the items in here are literally expensive so you can quit this if you are not up to expensive clothes but I also highly recommend this store because they really have a wonderful and great quality selection of clothes which mostly comes from a good brand.

Penelope's is truly a gem! During my visit yesterday, I found myself in need of some retail therapy as it was a challenging day for me - I always make it a point to go shopping on my late mother's birthday to honor her memory, as she was a big believer in the healing power of retail therapy (and her wisdom never failed me, haha).

Been a fan of the shop for quite some time. When I lived in the neighbourhood I loved to browse the new fashion and nick nacks. Now that I don't I still come on down to take a look or browse online. Stop in and take a look, your closet will thank you.

My fav Wickertown boutique. Spendy but so worth it!! High end unique brands!! Gorgeous layout

Really great clothing boutique on Division Street. The fashion tends towards casual and comfortable. There's a great selection for all body types which I appreciated.

Since the first time I saw the dress that my sister had purchased from this shop, I've had a strong desire to pay this boutique a visit. I really liked the dress that she wore to the party that we went to together. That is why, I insisted that she come with me to this store and assist me in selecting the dress that will look the most flattering on me. And I am so grateful that we were able to find one; it is of such refined quality for me. I gave it a shot once while out on a date, and both me and my partner liked it. I cannot express how grateful I am that I was able to find this store. Absolutely worth every penny. I will definitely recommend this store to my friend. This is the kind of boutique that every customer will really adore.

I like the men's collection of this store. The clothes definitely have a great quality and design. Most of them comes from a good brand and there are various casual and formal selection. That goes the same with their women's selection. The store is a typical boutique and it has a designated location just around the other stores in the area. It is clean and everything is well organized plus their staff are warm and accommodating. When it comes to the pricing, all of the items in here are literally expensive so you can quit this if you are not up to expensive clothes but I also highly recommend this store because they really have a wonderful and great quality selection of clothes which mostly comes from a good brand.

I came to this place and one of the staff greeted me. I look at their products. I can see some boxes on the floor. They should put it in the right place to prevent tripping hazards. There are only a few products I can see. Their products are cheaper and more expensive one. I came here to buy my husband a polo shirt. And I found a blue and white polo. My husband has a lot of white polo in his closet so I chose blue. It was thick and not too hot to wear. I think it will fit my husband since I know his size. I went to the counter to pay for it. The staff were too slow to prepare my purchase. She was busy talking to someone on the call. She should prioritize the customer first before calling or while calling. This place should improve.

I dont know what's going on here but is has something to do with the Kardashians: Saint mason ('s) reign (in) stormyi north (west) Chicago Penelope dream true There is something happening at this store.

Owners are super sweet. I'm always stopping in to see what new stock they have and I'm always impressed. I've been shopping here for years and think they've got some of the best more independent, private label collections for men and women at a great price point. Also. They have incredibly cute children's clothing. Stylish af. They've also got seasonal sales all year long. Look out for them during renegade festival as well!

Not inviting customer service at all. I walked in and was planning to shop, but there were 2 young ladies that never spoke or even came from around the sales counter. This confirms that Nordstrom has far better customer service and I will continue to shop at Nordstromok and spend my money.

EXPENSIVE!!! Ok? If you can't afford it, move along. I don't think that means you should give a place a bad review. It just means that you can't buy anything there. Sacks 5th Avenue is too expensive. I'll tell you one thing, their Freitag bags are cheaper at penelope's than buying them from Freitag online. Their Zuriick shoes are quite affordable. I found a ton of shirts in their sales boxes (in the back of the store) that were 80% off. That's getting pretty close to affordable. Okay, make that, "I'll tell you 3 things." So I bought some shoes, a bag, and shirts, and then an APC coat which was way too expensive, but where are the dirt cheap APC coats? APC is always over-priced, but not because Penelope called them up and made them charge a lot for their clothing. They have a little pug that runs around there, smelling your toes. For some reason, that's a plus. I think that for a boutique it's pretty awesome, the staff was friendly to me, and it wasn't torture to shop there, which is great for a guy.

If it weren't for the snootchy-bootches that work there, I'd probably visit more often. I find un-customer-friendly people to be extremely annoying when they are working in the customer-service industry. This ain't Reckless Records people, it's fashion. If you can't be bothered to do your job or you hate your job, move on. I used to be that person too and then I got a new job, see how that works?

This is by far my favorite boutique in the neighborhood. I LOVE their style, everything in there is so cute and they have a fantastic selection of datebooks, notebooks, photo albums etc. Even though I can't afford to buy the clothes here it's a great place for gifts or fun little things for myself. And if I ever start banking I will definitely shop here for clothes! Actually not all the clothes are super expensive I'm just in the very low end of the clothing budget spectrum myself. Great selection of guy's clothes as well, they always have tshirts I really like that I don't see anywhere else. The staff is friendly when you ask for help but never pushy which is great. ALSO bonus star for having two adorable obese snorty pugs that live in the shop!

I am still riding the high from discovering that Penelope's carries my favorite, impossible to find in the states line from Paris - Sessun. I went bananas and picked up several dresses, belts, and boots. Prices were super reasonable for the lines they had, and I actually managed to find some stuff on sale in my size. This never happens. The sales people were super friendly, not pushy at all, which is a pet peeve of mine about boutiques. If you're into leggings, tunics, flats, dresses, belted tops, etc, this place has TONS of finds. I still can't even handle the fact that they carry Sessun. New fave boutique. By far.

Love this place. As a Scandinavian, I dont really love the american dress code. Luckily this cute little shop exists with its swedish brands, and more european clothes. More pricey than H&M, yes. But what do you expect?

Why does everyone have beef with the prices? I get that the goods here cost more than Urban Outfitters. But I am not remotely interested in using Urban Outfitters as a measuring stick. I go here for APC, Sessun, or Pink Studio accessories. Or for the adorable jewelry by Lulu. I find that Penelopes is quite reasonable compared to it's neighboring boutiques. I know every business has their bad seed employee(s) but I've never had an unpleasant encounter with any of the staff. I get the sense that other reviewers' frustrations with their own budgets and their own insecurities has more to do with their experience than the actual service in the store...

The stuffs are cute but the prices are not. I know that much. Sometimes I also question the quality of the products they carry. I know it's probably not their fault but it just pissed me off when I purchased a $120 worth of lamb skin ballet flats and I got holes after wearing them for 2 weeks. WTF?!! Customer service was okay. I've never felt that I was ignored. Maybe I just paid more attention to the clothes than to them. So I can say we're even. What I love most about this place? The fact they have miss pac-man and 2 cute pugs!

I love the people who so arrogantly imply that anyone spending money here is doing so for hipster cred- guess what you sound like? Yes, a hipster. And I totally agree with you Crystal M., people who constantly complain about how expensive everything is just come off as poor and bitter about it. The world doesn't owe you anything. That said, I think Penelope's is amazing. The girls that work here are always friendly and helpful, there is a good rotation of merch so there's usually something new and cute to check out. I am a Spiewak freak, Cheap Monday is a nice alternative to dropping $100+ on denim and I got simply the best... planner... ever. I am sooooooo happy to see they have an online shop now since I am stuck up here in Nano Cericho until I make my way west next fall. *lol- just realized I'm wearing a tee from Penelope's in my pic :)

I really like the style of this place -- with its decor that references 60s British Mod. Nice selection of clothes, including Ben Sherman. However, now that some of these labels are available in discount places like Nordstrom's Rack, I can't bring myself to pay $60 to $90 for a shirt or sweater than I can get for $30. I like the shop -- if I ever make more money than I need I'll come again.

Love it. Walked in here randomly one cold Saturday night. Sales people were "eh", but I sort of like them that way. I like to shop by myself with myself ... it's "me" time. The clothes are fun. I like simple clothing -- this place worked out great for me. Simple and cute with being too boring. The prices, oh the prices. Such is life. Can't wait to go back!

I wish everything in the store was like 20- 50 bucks cheaper. Youll find the cutest dress and itll be just over priced. I don't know whose fault it is- the designer or the store? or maybe it is me for not having enough money but really admiring it? Ugh- they had all these really cool paper rad tshirts the last time i went in there.

I love Penelope's. At first it bothered me, it reminded me of every little store in Japan that I couldn't shop in because all the clothes would be too little on me, and that annoyed me. But, luckily the sizes here are more fitting. It's expensive..yes, but they have some pretty cool stuff...and lucky enough for me, it's right around the corner from my house, so when they have a sale - I'm all over it. The sales are always pretty great, so watch for them. Some of the things I have bought here on sale have become permanent staples in my wardrobe. When in doubt this is where I get my husband a little gift for any occasion...he loves the mens clothes in here and any other little doodad they may have.

My favorite little boutique in all of Chicago. They have beautiful things for your home and your body! Not only do they carry independent designers, Japanese imported paper goods and great shoes; they also carry adorable little prints scattered on the walls. It's a great place to buy a gift for someone that's a little more unique than the hipster conglomerate known as Urban Outfitters. This place attracts young, creative individuals and is definitely an inspiration for myself as a designer. Oh! They also have a BRILLIANT sale section. Amazing prices! Check it out!

Really fun store, they have some cool t-shirts from [im]perfect article tees. I have to agree that the prices are high, but the store owners are so kind and they own two pugs and have a little toy pug mascot sitting near the window! *Rolling over another star for their coolness factor.

Like everyone else said, Penelope's has great clothes but prepare to go home with an empty wallet. Penelope's carries a lot of hard to find small labels that I wish I could afford, most of my time there is spent browsing. Occasionally, something will go on sale and be alllmost reasonably priced but still kind of a splurge. This is definitely not the place for everyone but it's fun to look around and pet the pugs or try on something you know you can't buy. It's also a good place to get some inspiration if you do a little sewing at home.

This review is for their online shop. I lived in Chicago for five years and patronized several independent boutiques across the city. I never heard of Penelope's, and now I know why. I came across Penelope's when I did a Google search for a couple brands I like. I was drawn to their selection of American and European brands that aren't easy to find in conventional department stores -- even high-end retailers like Barneys or Bloomingdale's. As luck would have it they were having a summer sale online. I e-mailed them a question in mid-July; never heard from them. I tried calling them during business owners on two different days. What does the voicemail say? "E-mail us." In other words, their employees don't want to talk to their customers. Nevertheless, I really wanted this one sweater and jacket particularly because they went on further reduction. I go ahead and purchase these items online. (Minimum $150 for free shipping.) The positive thing I could say is they sent the package the next day. I placed my order on 8/3, it was sent on 8/4 and was supposed to be received in San Francisco on 8/8. Here's where another problem arose. Their package required a signature which is a good thing in many ways. This helps ensure the package is received. The issue is - like most folks - I am working between 9-5 and cannot be home to sign off for the package when USPS delivers. I missed the delivery because I was working. I requested it to be redelivered on the 9th; it didn't come. It wasn't received either on the 10th. According to the Penelope's order confirmation+shipment e-mail, we should contact them if the order isn't received within two days. I e-mailed Penelope's on that second day. Never heard back. I called again; straight to voicemail. Moreover, when I received my order the sweater's price tag was re-marked with a lower price than what I paid so in essence my reduction should've been lower with their "extra 25% off sale item" offer. But you know what? I'm so disappointed by their one-way communication and poor customer service that I won't even bother asking for that further reduction. Chances are I won't receive an e-mail back. So... Penelope's has fantastic brands and a nice selection of clothing, but incredibly problematic customer service. Perhaps their in-store service is better though some of these Yelp reviews suggest otherwise. I'll say this for sure: their e-commerce and communication needs some help. If a customer calls, someone should pick up. No store is that busy to avoid *all* telephone calls. If a customer sends an e-mail (or two!), someone should reply. If you intend to purchase something from Penelope's online, I send you *the* BEST OF LUCK!

They actually have a pretty dope men section. I just walked in to browse but ended up buying a couple of Cardigans. The prices were very reasonable, and the styles were really cool. Super nice staff that was very helpful with finding me the right sizes. Dope spot.

I love this boutique. I am a TOTAL sucker for APC and they have the best selection i've seen in the city. The girls that work here are super cute & friendly and always helpful without being intrusive (great since I'm a wierdo and was probobly here for more than an hour once or twice :p ) Found a great pair of not cheapy plastic but NICE plastic wayfarers for $10 that i sadly left inside a locker at six flags. There's always local art hanging on the walls and it changes up every so often. All the clothes are super cute and they have lots of smaller, lesser known indie designer clothes. Lots of cute trinkets (great for gifts!) and also super cute jewelry. Great selection of guys clothes here as well. In the back there's always a great selection of sale merchandise that is definately worth checking out. For those who are from out of town they now have a webstore :)

I wish I could have more money to buy up everything here. Penelope's is by far the most ethereal store in Chicago. I LOVE everything that they carry, display, and conjure here! Just wish I had the ca$hmoney$ to put it all in my closet. In any case, the store is very charming. Meaning it looks charming without being actually trying to be "vintage" like. Beautiful selection of clothing for both woman and men.

Very hip clothing store for men and women. The clothing are by a lot of unknown designers so they tend to run on the expensive side. A lot of the pieces in the women's section are reminiscent to those of the Marc Jacobs and Chloe lines. If you like the way Sofia Coppola dresses, you'll probably like something from here. The men's clothing is very hip/club/untitled store type stuff. Cool indeed but also pricey. The accessories they have here are the draw. They've got guitar straps, wallets, shoes, bags - all one of a kind. Enter with $200!

Penelope's is pretty much your standard independently-owned hipster/trendster boutique: kind of like an Urban Outfitters with higher prices, less fugly clothing, and a bit more street cred. The store is basically a large room filled with a few racks of clothing and several random counters of trinkets, indie magazines and accessories. I've found that a small ratio of product to store square footage is an almost-foolproof predictor of high prices, and Penelope's definitely follows this trend--if you have money to burn on $50 mittens and $16 notebooks make from grody recycled paper (I shit you not), you'll be in your element here. To temper the negative with something positive, I will admit that I did happen to find The World's Greatest Hat here (which I've been wearing almost constantly over the last few days) at a pretty reasonable price. Definitely not worth a special trip to Wicker Park, but if you find yourself wandering aimlessly through the neighborhood and want to view a great example of gentrification, you should definitely drop by.

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.

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!

I was a bit disappointed after hearing rave reviews about this place. I liked the decor far more than the clothes. They had some colorful stuff, but it wasn't my style.

Have not been to the store, but ran across them at the 9/25 Dose Market. Excellent selection of men's duds and accessories. I gave in to a great cotton scarf, perfect for my boho woodsman thing I'm trying out. Must definitely go and check out their store, but I'm afraid I'll go a bit nuts and buy the whole damn place. Wonderful ladies, cute and charming, were eager to help and chat.

Yes! A brown sound dealer outside of the internets and new york. Grand shop and great selection of clothing for men and women. Although i didn't buy anything, i will surely be back. Quaint atmosphere- doesn't feel cramped or over designed. This is a great store, tell your friends and check it out. Expect an update the next time I walk out of there. Hopefully not broke.

It's like a mini Portland in a storefront. Fits my ideal style to a T. I feel whimsical when i come visit..Love the layout, cleanness, staff, and selection.. Though I can't always get my pockets to fork out the cost..I still love seeing what's new in there..

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.

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.

GO! this place is marvellous. i think it might be the only place in chicago to carry built by wendy. i remember visiting this place 5-6 years ago when i was in high school, working part-time at a greenhouse, and actually being able to purchase something. ugh...thank you college.

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!

Penelope's is a fantastic neighborhood boutique; it's the type of unique gem that I search for when I travel. The clothing and items in the store are distinctive and merchandised in a way that makes the space easy and fun to shop in. It's great that they have brands that are difficult to find in a retail setting, like Built by Wendy and Freitag. Penelope's does a great job outfitting the store with items of different price points as well. I've picked up quite a few things here; from dresses to tops to jeans and stationary. Oh, and the sale section is awesome! The employees are helpful when you have questions or would like to try something on, but remain laissez-faire as you shop. I appreciate this.

This place stocks a very good selection APC as well as other lesser known brands of the same style. Friendly staff with cute dogs and free pins with the dogs on them. Amazing right?

Seriously. You guys. This is not a joke - treat your customers better. No one likes walking into a store where its associates don't say hello and deign to smile at customers. Stop being judgmental because I don't look expensive when I walk into your store. No one ever comes to check up on me when I'm browsing, and I am afraid to approach you guys. I'm tired of this! Can't we all just get along in the name of cute clothes? UGH. Although the clothes here are amazing, the service is below amazing. Too bad.

Unlike at many other Chicago boutiques, Penelope's people aren't impressed with themselves. Yay! Also happy they sorta keep Weekend Records/Soap alive. You can find classic and funky clothes here. I still wish I'd bought this print that was on the wall...was that 2 years ago?

I wouldn't complain about the pricing here as much as the dirty, cluttered atmosphere. Is this a "vintage" or "thrift" shop? Is this a store for "hard-to-find" designers? Is this a pet shop (I agree with the reviewer who complained about the smell)? Trying to be all things to all people, it fails to find a niche. I first read about them on Lucky Online and was disappointed in their favorable review...it's truly not even in the top 100 Chicago stores...the selection is NOT original, and there is PLENTY of attitude from the staff. That being said, I don't know why people complain about the prices, of all things...that's what clothes COST.

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.

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.

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!