Over the years, Bucktown's shopping artery of Damen Avenue has seen plenty of big-name designers (Cynthia Rowley, Nanette Lepore, Marc by Marc Jacobs, Alexis Bittar) and chain stores (Club Monaco, Bebe, Lush) move in. This itinerary focuses on the strip's top independently owned boutiques, so you can take the "shop local" approach to the most fashionable extreme. Women's clothing dominates, but there are a few gems for men.
Start your trip right by the Blue Line's Damen Avenue station, where City Soles (1566 N. Damen Ave. 773-489-2001) awaits with offbeat shoes for men and women.
Then check out the well-curated mix of up-and-coming and established labels at P. 45 (1643 N. Damen Ave. 773-862-4523), one of the first shops to settle on this now-busy strip back in 1997. Find laid-back clothes for guys on one side of the store and girls on the other at Riley (1659 N. Damen Ave. 773-489-0101).
Comb the racks of unique, splurge-worthy dresses and separates at
Helen Yi (1725 N. Damen Ave. 773-252-3838) channels the minimalist look, with big-ticket labels and the occasional sales-rack steal, while Clothes Minded (1735 N. Damen Ave. 773-227-3402) stocks plenty of mix-and-match basics.
At T-Shirt Deli (1739 N. Damen Ave. 773-276-6266), you'll find customizable T-shirts instead of cold cuts in the glass display cases.
Hidden below street level but worth a look, RSVP Gallery (1753 N. Damen Ave. 773-770-6666) stocks everything from Kanye West's limited-edition scarves to Billionaire Boys Club baseball caps.
Just north, stop in the namesake shop of local designer Michelle Tan ( 10) (1872 N. Damen Ave. 773-252-1888) before moving on to Edith Hart (1917 N. Damen Ave. 773-252-3350), which stocks unique, hip clothing and jewelry for ladies.
Up the block, Dress Up (1937 N. Damen Ave. 773-235-7780) features its namesake garment in all sorts of styles, but also carries separates, jewelry, handbags and shoes for good measure.
Continue north past Armitage Avenue to Violette (2031 N. Damen Ave. 773-235-7150), which eschews pricey stilettos for walkable (but still fashionable) women's shoes, all in the $20 to $60 range.