The Blog

  • We almost can’t believe it ourselves, but it’s been 11 years since we first cracked open the doors at 1913 W. Division. 11 years since we started a store with the intention of selling clothes we love to people we care about even more. Since then, we’ve gained staff, gotten more inventory, moved things around, and have introduced new brands, but the core thing, the thing that has remained throughout is our desire to make a connection with the people that come in to the store, and to truly be a place where anybody can find something that they love as much as much as we do. That’s why, to commemorate this special Golden Birthday, we’re throwing an 11th anniversary party on Friday, October 11th (pretty fitting, we think). With that in mind, from 6-8 PM we’ll be mingling with friends, snacking on local food (from Publican Quality Meats) and drink (from Half Acre, 3 Floyds, and Crafthouse cocktails), and offering a special deal on our new fall collections. So stop by, say hi, pet Penelope the pug (the store’s namesake is coming out of retirement for one night only) grab some food and drinks, and let us show you our appreciation for helping us grow so much over these past 11 years.


    We hope to see you there, thank you for your support!

  • If you felt like the boys were getting all the best textiles these days, think again. Ace & Jig brings the coolest custom-textured and patterned cottons to womenswear, and the fall 2013 collection might be their very best collection yet. From black textural stripes and charcoal checks, to metallic stacked triangles and autumnal burgundy plaids, all of Ace & Jig’s fabrics are responsibly manufactured in India. Dressing for fall couldn’t be easier with this line. Just throw on a dress with tights, or tuck a buttondown into jeans. Say goodbye to synthetic silk-wannabes and pick-up the kind of natural textiles you can wear year after year. It’s all online and in store!


  • There are shoes, and then there are shoes. Rachel Comey footwear falls into the second category. Yes, they have a $300+ price tag, but that’s because they’re high-quality in terms of materials, construction, and even aesthetic. At Penelope’s, we’re all about her boots for fall. The cult Mars ankle boot, which she’s made for years and which almost all our employees own; the newer, shorter, low-heeled Dorsey ankle boot; and a classic knee-high version called the Rubie boot. Constructed from thick, supple leathers in deep browns and blacks, these boots elevate every outfit. Suddenly, jeans and a tee or a simple dress look cool, smart, and sophisticated. The bottom line? Rachel Comey’s fall collection is most definitely worth an investment. Grab a pair in store or online!


    And a little advice: her style’s run narrow, so be prepared to size up. Also, the leather stretches, so that painfully tight fit will expand with just a week of wear. You do want them to be a little snug, initially.


  • Our Legacy plays around with the idea of service uniforms this fall. Think Bill Cunningham and his blue French workwear jacket but more slick and by-way of Sweden. The collection features leather, silk and other exclusive fabrics mixed with contemporary synthetics. The cuts are boxy and utilitarian, copied from classic waiter and maintenance men uniforms. All in all, the “Official” collection is about a smart new perspective on high-low dressing. Watch the fall 2013 collection video below to get a real sense of this brooding, edgy, minimal collection. Then visit us online or in store to see the new arrivals for yourself!



  • Sessun takes us to a sad, grey beach (but flamingos are present, so it can’t be too sad) for its Fall 2013 collection video. Against a bleak background with an eye-catching stork traversing the frame, Sessun’s models show off the collection’s versatility and layerability in contrasting jewel and sepia tones. It’s a video that is at once beautiful and informative, and is made even better with the knowledge that virtually the whole collection is now in-store and online, so you too can wear pieces from this sophisticated, yet playful collection.




    Clockwise from top left: Fall Florea Sweater, $225; Chorus Hooded Parka, $335; Bedford St Slim Pant in Hazelnut, $178; Asuki Blouse, $174.



  • HELLO: APC Fall 2013

    APC's fall collection is always one of the first signs of the changing seasons ahead, and because of the unseasonably cool, breezy weather it didn’t seem premature to pull out the fuzzy knits, thick canvas skirts and lightweight sweater dresses from our first shipment. Per usual the crux of APC’s collection is their high-quality, classic separates: textural jersey tees and canvas a-line skirts for women; checked flannels and gorgeously colored pullovers for men. Take a look at their fall lookbook to appreciate the 60s/70s/80s references abound and get inspired for the fall and winter ahead, and don’t forget to check-out our (REDESIGNED!) webstore for all the new arrivals!


  • Say hello to the new Penelope’s webstore! As a 10+ year-old small business with a 5 year-old online store, we thought it was high time for change. And after months of late nights and fusses over fonts and layouts, we’re excited to announce that the new is up and running. The new site features bigger and better images, more functional and shop-able catalog and style pages, and a clean layout that should make shopping the site easier than ever. We hope will be pleased with the new design!

    You might notice, too, that our logo is different. Out with the old--all the old--and in with the new, we say! Huge thanks to Eden Halperin for all of his work on the site. And please let us know what you think; we welcome all feedback!
  • Yes, it’s that time again. Renegade Craft Fair is next weekend, September 7 - 8 from 11 am to 7 pm daily. Each year the fair’s bigger and better, and, for 2013, it stretches between Damen and Paulina. That’s six blocks of fine craft goods and tasty treats to be enjoyed!

    We’ll be offering our own sale fare--sidewalk racks filled with clearance items & final summer markdowns! We’ll also have all our newest fall arrivals on display in store. Hope to see you this weekend, join the fun!

  • Sessùn takes us to a sad, grey beach--with flamingos!--in its Fall 2013 collection video. Against a beautifully bleak background with a poignant stork traversing the frame, Sessùn’s models show us how to layer for brisk weather in contrasting vivid jewel and washed-out sepia tones. You too can look dreamy-melancholy-cool by juxtaposing Sessùn’s tweedy outerwear with superfine knits and printed pajama silks. The first delivery of this sophisticated, moody collection is now in store and online! Take a look-see!


    Sessùn Video Fall 2013 from jas000 on Vimeo.



  • It's that time again! This weekend we will be teaming up with the best boutiques & designers in Chicago to bring you CHEAP THRILLS, a weekend-long super sale event in the heart of Wicker Park. There will be loads of women's and men's apparel, accessories and home goods from previous seasons marked down 40% off and more.

    1564 N. Damen, 3rd floor
    above City Soles


    Saturday, April 27 11am - 6pm
    Sunday, April 28 12pm - 5pm

  • Our Friends at Unison are having their SHIP / SHAPE LAUNCH PARTY tomorrow night. They will be debuting new artist collaborations: ANCHORS by Cody Hudson + SHAPES by Alex Fuller. Check it out. APRIL 11th 6:00-8:00pm at Unison / 2000 W Fulton St, F-109.

    We also had a lot of fun helping them with their spring/summer catalog shoot

  • One line that we are very excited about in store right now is The Pendleton Portland Collection.  The Portland Collection was born in 2011 when Pendleton Woolen Mills joined with three Portland based designers; Nathaniel Crissman, Rachel Turk, and John Blasioli to create an original and modern line using classic Pendleton fabrics.  The outcome: Brilliant!  
    We couldn't be happier to have them back in the shop for their second season!
    Some of our in store favorites are the accessories.  From scarves worth drooling over; to clutches, ties, and umbrellas - you can't go wrong!  They also make great gifts..  'tis the season! 
    Here are a few accessories that we love from the collection:

    Check out more clothing and accessories from The Portland Collection in store or on our website!
  • The Hill-Side has come through with their incredible fabric sourcing abilities, once again.  Their Fall 2012 collection, which has introduced bow-ties into the mix, is killer!  Made up of unique ginghams, chenille knits, bright polka dots, and blanket knits - we want them all!

    Check out some of our new Hill-Side accessories on our website.


    Did we mention their amazing new lookbook?  They sent disposable cameras to their retailers across the globe and the end result was an incredibly candid and original lookbook.  Plus, you may see some familiar faces ; )  Check it out here.
  • We wanted to share a few shots from our booth at NorthernGRADE Chicago.  We met some awesome folks, saw lots of cool stuff, and had a great time!  The event took place on Oct. 27th, it featured U.S. made menswear and went off without a hitch thanks to our friends at Well Spent and Pierrepont Hicks.


    Check out this article from CNN on NorthernGRADE Chicago. Thanks to all that made it out, it was great to see you!

  • We are thrilled to be sponsoring this Saturday's NorthernGRADE Chicago! 


    We will be bringing along some of our favorite American-made menswear brands such as:
    Gitman Vintage, The Hill-Side, Pendleton (including The Portland Collection), Gerald & Stewart, Filson and other various clothing and accessories.
    Stop by and enjoy some coffee and treats as you shop, as well as some brew from Half Acre Beer Company who will be tapping their kegs around 3:30pm.

    Hope to see you there!
  • Come check out the new 2012 Button-O-Matic series from Busy Beaver Button Co.

    These totally rad designs are specially curated by the folks at Delicious Design League who have teamed up with Busy Beaver for their 10th anniversary edition of the Button-O-Matic series:

    We love them!
  • We are honored to be presenting a collection of new prints by Chicago artist (and long time friend of Penelope's) Alex Valentine. Join us for an opening reception this Sunday, October 7 from 3-6 to see the works, meet the artist, enjoy some light refreshments, and check out our new fall styles.

    Alex has also made a limited edition tote bag to be released at the opening, available for free with purchase of a print or of $150 or more, while supplies last.

    Recently, we caught up with Alex at the print department of the Art Institute of Chicago to discuss his work and what we can expect from the upcoming show. 

    PENELOPES: Please tell us a bit about your history and projects you have going.
    ALEX VALENTINE: I grew up in Boston Massachusetts. I moved to Chicago to attend SAIC. I am now an instructor in the Printmedia Department where I teach courses in offset and screen-printing. I am a co-founder of No Coast, a publisher of artists editions and projects.
    When did you start making your art and how has it evolved since?
    I started making images and prints as promotional / informational material ( posters, zines, and packaging) for bands. My art is still promotional. I view my prints as announcements, maybe in an extremely general sense. Now the work promotes actions and characteristics instead of specific events or things. I am drawn towards life actions that are fun, social and cooperative, so I make posters to champion those actions. Printmaking gives me an opportunity to be endlessly variable and additive.
    Could you describe the printing process you use?
    Offset is commercial lithography. It is used in industry to print books, magazines, newspapers, packaging, and posters. It’s suited for large runs of printed material. I used it initially to make a book.  Then I got really excited by the possibilities of creating a large volume of prints. It suited the projects I was working on. I trained as a press operator and have gradually adapted the press as a drawing tool. 
    Tell us a little about the pieces we currently have in the store? 
    The prints currently in the store are part of a portfolio called Sugamo Heads. Its named after a neighborhood in Tokyo that I stayed in for a few weeks. The images are inspired by that trip and the graphics of that city.
    We are excited for you to show new works at Penelope's, tell me a little about what we can expect? 
    The work for Penelope’s is a series of one color offset prints. They form a folio of prints called Marathon Smudge. I tend to work in series as a way of organizing my experience as an artist. 
     Where can we point people to see more about you and your work?  
    My instagram handle is Pristinechicpea :-)
    Thank you Alex for allowing us to show your work, we hope everyone can make it out for the reception on Sunday!
  • Gitman Vintage have truly outdone themselves with their Fall/Winter 2012 selection of Shirting.  From incredible soft and warm Portuguese flannels to lighter weight pinpoint oxfords, their archive fabrics and prints are something to pine over.  Not to mention some great ties to boot!

    Check out our full selection of Gitman Bros. Fall/Winter 2012 collection here.

  • Sending a huge thanks to the readers of Chicago Magazine for voting Penelope's readers' choice "Best Boutique"!
    We are so honored! 

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1913 W. Division St.
Chicago, Illinois 60622

(773) 395-2351

Monday - Saturday 11-7
Sunday 11-6