Chicago - Shopping - Laid Back Casual

1919 W. Division St., Chicago 60622
773-252-2520

Casa de Soul

Browse through a wide array of merchandise from one-of-a-kind hoodies and vintage tees to over-priced little dresses, indie magazines, jewelry and decor interior pieces from Africa and Asia. Ladies... read more

1804 N. Damen Ave., Chicago 60647
773-395-2999

Apartment Number 9

Clean, sophisticated looks that lean towards classic rather than trendy dominate this Bucktown men's boutique. Geared towards the fashion-conscious male in their 20s-40s the owner proves his consis... read more

101 E. Oak St., Chicago 60611
312-280-1637

Juicy Couture

Comfy cotton separates, daring short dresses and California casuals swooned over by Legally Blonde followers. Apparel embellished in gold and insignia targeted to the 14-26 age range, favorite long... read more

46 E. Walton St., Chicago 60611
312-255-8360

American Apparel

Founded in L.A. in 2003, hipsters flocked to work within the white-lacquered walls of American Apparel, hawking their rainbow of basics, and looking the other way when their friends swiped a hoodie... read more

837 W. Armitage Ave., Chicago 60614
773-880-9801

American Apparel

Founded in L.A. in 2003, hipsters flocked to work within the white-lacquered walls of American Apparel, hawking their rainbow of basics, and looking the other way when their friends swiped a hoodie... read more

1563 N. Milwaukee Ave., Chicago 60622
773-235-6778

American Apparel

Founded in L.A. in 2003, hipsters flocked to work within the white-lacquered walls of American Apparel, hawking their rainbow of basics, and looking the other way when their friends swiped a hoodie... read more

929 W. Belmont Ave., Chicago 60657
773-472-0500

American Apparel

Founded in L.A. in 2003, hipsters flocked to work within the white-lacquered walls of American Apparel, hawking their rainbow of basics, and looking the other way when their friends swiped a hoodie... read more

2202 N Halsted, Chicago 60614
773-281-9590
Perk

True Religion

Cult of west coast celeb followers including Jessica Simpson and Miley Cyrus save the brand a permanent spot in the weekly gossip rags. Booty enlightening conspicuous horseshoe (or is it Buddha's s... read more

1000 W Armitage, Chicago 60614
773-525-4627

Rugby by Ralph Lauren

Based around the über prepster Rugby Polo Jersey. Items from this Ralph Lauren subsidiary top teen and college kid back-to-school wish lists. Broad stripes in Ivy League color combinations on ... read more

1426 N Milwaukee Ave., Chicago 60642
773-360-8182

Brooklyn Industries

Started with messenger bags made from billboard vinyl, now becoming a full-fledged New York institution. Artist-owned and managed retailer runs under the philosophy: LIVE, WORK, CREATE and creative... read more

1702 Milwaukee Ave. , Chicago 60647
773-227-9930
Perk

Scoop

Unadorned space requires a bit of digging to "scoop" finds from racks abound with everything from obscure designers to Missoni and Alice + Olivia treasures. Wide range of contemporary and designer ... read more