Second City

While Frank Sinatra may have dubbed Chicago's State Street a "great street" with its grand department stores and bubbling commerce, locals know that nowadays the best fashion is found off the beaten path, especially when it comes to vintage. From Japanese influenced Yellow Jacket to the couture lines at Leslie Hindman, there's an abundance of vintage and second-hand fashion to be discovered in the Windy City. Naturally, that makes Chicago, our kinda town.

• Eskell, 1509 North Milwaukee Avenue; 773-486-0830

In a quaint storefront on Chicago's Milwaukee Avenue, Eskell combines new and old alike. Designers/owners Kelly Whitesell and Elizabeth Del Castillo's own cute old-world-inspired line is arranged along side a slice of vintage heaven. Counting thrifting among their passions, the duo often spend weekends thrifting in their home-state of Indiana looking for undiscovered gems. "We love pieces that create a sexy secretary look," said Whitesell. The owners often alter vintage dresses, too, to bring out the best in the original piece. Here, Eskell also stocks vintage accessories, shoes, belts, and handbags. Best of all, vintage ranges from just $15 - $45.

• Lennie and Me, 1463 North Milwaukee Avenue; 773-489-5576

Brimming with with one-of-a-kind vintage pieces and designer resale of labels like Marc Jacobs, Chloé, and Gucci, Lennie and Me stands out as vintage boutique with personality. The shop is known for its selection of full-skirted cocktail dresses, perfect little fur coats, and bold jewelry; but best of all is the array of decades-old hats--a must for any true vintage fiend.

• Una Mae, 1528 North Milwaukee Avenue; 773-276-7002

Trolling through Una Mae's bi-level space is an ideal way to spend a lazy Saturday afternoon. Una Mae has a distinctly laid-back '70s feel that comes from its peppering of funky furnishings alongside vintage fashion. Combining thrifty finds such as sharp western shirts, sundresses, and cardigans alongside trendier labels like Paper Denim and Cloth jeans and Tulle, the store gives off a vibe that is relaxed and inviting, which makes it a favorite among locals.

• Knee Deep Vintage, 1425 West 18th Street; 312-850-2510

A year-long, cross-country vintage scouting trip found Trent Marinelli and Carlos Lourenco drowning in vintage finds. In March 2008, they opened their quaint boutique in Chicago's Pilsen neighborhood. Specializing in clothing and housewares from the world war II era through Regan-omics, the shop has something for every occasion. Knee Deep Vintage hosts roving events such as a recent Back Yard Sale in Williamsburg, Brooklyn, and an art show at the Chicago location. With their insanely reasonable prices, (items average $10 to $24), Knee Deep is one of the city's best bets for throw-back finds.

• Land of the Lost, 614 West Belmont Avenue; 773-529-4966

This fresh, sunken-level vintage shop is '70s and '80s vintage salvation. Looking for an original KISS T-shirt or a genuine Star Wars Return of the Jedi T? This is the place. The selection is laced with irony, and the owners shop eclectic: Expect grand-dad cardigans, jeans, and rock T-shirts in abundance. In addition to clothing and accessories, there are other miscellaneous treasures and toys that spark teen nostalgia.

• Leslie Hindman, 1338 West Lake Street; 312-280-1212

For the couture belle in all of us, Chicago has a fairy godmother: Leslie Hindman. Leslie Hindman Auctioneers hold four regularly scheduled Vintage Couture and Accessories auctions a year, saluting the original, innovative designers who set trends and standards--Christian Dior, Givenchy, Chanel, Pucci, Courrèges, Pierre Cardin, Hermès, and others are often on the block. A gorgeous and still very contemporary, 1997 pink Versace dress was among the items auctioned off recently. And while the items at Leslie Hindman aren't exactly for the budget collector, the occasional splurge on a timeless piece is well worth the extra bank.

• Yellow Jacket, 2959 North Lincoln Avenue; 773-248-1996

Yellow Jacket is a well-worn card in any Chicago fashion girl's Rolodex. The shop was born out of owner Jennifer Rau's frequent travels to Japan in the early '90s where she set up flea markets and fed her love of all things vintage, which imbues her treasure troves today. One-piece jumpsuits and chic plaid jackets are common-place. A midwestern staple for vintage rummagers, the store has a Chicago location and one in Milwuakee, too.

Our local Chicagoan digs up 7 vintage shops for making the past perfect.