December 11, 2009

First Markdowns!

We are happy to announce a new look for The site is updated with tons of NEW fall and winter items as well as the first markdowns of the season. As always, shipping is free on all orders over $150.

December 4, 2009

Do Division Holiday!

Join us this Saturday, December 5, for the annual Do Division holiday shopping walk. Come by for the first markdowns of the season and receive a free gift with every purchase. Save 20%-50% off the original price on loads of men’s and women’s clothing, accessories, and housewares from your favorite lines.

Stop in for some refreshments and pick out a gift for a friend or yourself. Hope to see you this weekend!

November 25, 2009

Shinzi Katoh Sale!

Select Shinzi Katoh items are now on SALE!

double lunch box
(was $20) $14

Shinzi Tote
(was $40) $29

Shinzi Round bag
(was $48) $29

(was $38) $29

November 21, 2009

Sale Marais!

Marais tuxedo boots and oxfords are now on SALE!

marais oxford
(was $85) $59

marais tuxedo boot
(was $145) $118

American Retro

Two perfect Holiday party dresses from American Retro are on SALE!

jagger dress
(was $288) $199

bandol dress
(was $298) $199

November 19, 2009

Built By Wendy Hunting Jacket

Perfect for the chilly Fall weather! The Built By Wendy wool hunting jacket is on SALE!


A few items from Sessun's Fall collection. Winter white, subtle quilt-like star & native american motifs make each of these pieces perfect for layering with cold weather staples.

Sessun's beautiful winter coats and parkas are sure to keep you warm with fleece linings and thick wool. Not to mention all the irresistible details like wood toggles, bold plaids and leather tipped drawstrings.

November 14, 2009


Penfield was established in Massachusetts in 1975 & has built a reputation for making the highest quality down-filled jackets, fleece & outerwear.

Penfield Bags

November 8, 2009


Check out our new Basics sections for both Men & Women for all your favorite hoodies & tees.

Our Legacy

Stockholm-based label Our Legacy’s founding date is stated as 1980-81 on their website, but this is actually the founder’s respective years of birth. It was actually founded in 2005 by childhood friends Jockum Hallin and Christopher Nying. Christopher states that the goal behind the clothing is to “To create timeless garments in a natural, well-dressed, and comfortable way”.


Originally formed as a band and eventually reanimated into a fashion label, Whyszeck eventually found their calling in 2004. Their design aesthetic reflects a mixture of architectural & minimalistic influence as well as clips from music itself and its surrounding subculture. Their 2009 Fall/Winter lineup blends a geometric approach with an emphasis on interesting color tones.

September 12, 2009

Renegade Craft Fair!

Don't Forget! Renegade Craft Fair is along Division street this Saturday & Sunday. Crafters from all over the country will be selling their wares and we will be participating with a sidewalk sale in front of the store including final markdowns on summer clothing and accessories. We will have items on sale from craft and housewares lines including MMMG, Little Otsu, Shinzi Katoh, Sukie, and Fluffyco plus sweet deals like $25 shoes & sandals, $25 jeans, $10 tee shirts, and tons of summer clothes from 50- 70% off. Don’t miss out on this rare occasion for cool crafts and sweet deals at Penelope's!

New Fall!

Our fall collections have started to arrive including new styles from A.P.C., Cheap Monday, Dunderdon, Hyden Yoo, Marais, Our Legacy, Propery Of, SessĂșn, Shades of Greige, Spiewak and many others, with more arriving every day. We think that this is our best lineup yet, hope you come by to check out the new designs.

July 23, 2009

Summer Sidewalk Sale!

Stop by this weekend, July 25th & 26th, for our Summer Sidewalk Sale! We will have racks of Spring & Summer deals up to 75% off. Also, a little something different this year, we will have a selection of used clothing starting at $2.

Saturday, July 25 11am - 7pm
Sunday, July 26 12pm- 6pm

July 8, 2009


It's SUMMER SALE time at Penelope's. Starting this Saturday, July 11th, come by or log on to enjoy 20% to 60% off spring and summer clothing. We only do this twice a year, so now is your best chance to save big on your favorite brands.

We're open every day: Mon thru Sat 11 - 7, Sun 12 - 6
or shop 24/7 at

May 19, 2009

Do Division!

Join us for our annual Sidewalk Sale this weekend as part of Do Division street festival and enjoy 25% - 75% off on select spring and summer styles!

Saturday, May 30
11am - 7pm
Sunday, May 31
12pm- 6pm

March 1, 2009

Spring 2009: Plastic Island

We just received our first spring shipment from playful yet effortlessly classic collection Plastic Island. Here is a sampling of new dresses from this great line from South Korea:

Belted Sailor Dress

Block check Dress

Check V-back Dress

February 25, 2009

Cheap Thrills!

Please Join us this Saturday for the Cheap Thrills Warehouse Sale!

Saturday, February 28th, 2009

11am - 5pm

Around the Coyote Gallery
1935-1/2 North Ave. 2nd Floor

Penelope's is very excited to participating in this great multi-boutique warehouse sale. We will be joining some of the best Chicago boutiques: Eskell, Tangerine, & Veruca Salt as well as Brooklyn favorites Toni Hacker, designer of handbag and clothing line Hayden-Harnett and Shana Tabor, store owner and designer of clothing and jewelry line In God We Trust. We will be presenting 50% - 75% savings on women's fall and winter clothing as well as many early spring deals. This is an open event, so please pass this on to your friends. RSVP is not required but appreciated. RSVP via email to We are anticipating a crowd so come early for the best selection, hope to see you there!

February 6, 2009

Spring 2009 : A.P.C.

Here is a mini preview of A.P.C. Spring for men and women. Keep an eye out for more to come from this French staple.

Plaid Pocket Top

Dot Pocket Top

Corduroy Top

Multi Plaid Shirt

Merino Wool Cardigan

Blue Plaid Shirt

February 5, 2009

Spring 2009: Pointer

Pointer, founded in London in 2004, crafts well-made understated men's shoes. We love their simple lines and great fit!

Fairbank Sneaker

Cyril Boot

Cargo Wolf Shoe

Barajas Shoe