Vive La Femme
Kiyonna wraps and Igigi's beautifully cut cocktail dresses are highlights here, not to mention its roster of special events, like photo shoots with local studio Vavoom Pin-Ups.
2048 N. DAMEN AVE., 773-772-7429, VIVELAFEMME.COM
Isabella Fine Lingerie
Everyday wearable underpinnings—that are still undeniably pretty—are consistently stocked at this Chicago institution.
840 W. Armitage Ave., 773-281-2352, shopisabella.com
840 W. Armitage Ave., 773-281-2352, shopisabella.com
Kaveri
Tucked away on a quiet stretch near DePaul University, Kaveri focuses on slightly adventurous cuts, like cropped Rag & Bone bombers and slouchy Demy Lee cashmere sweaters.
1211 W. Webster Ave., 773-296-2141, ekaveri.com
1211 W. Webster Ave., 773-296-2141, ekaveri.com
Kokorokoko
Styled like an '80s Afro-pop parlor, this newcomer specializes in wildly well-priced vintage pieces (it's hard to find anything that tops $40), including grandpa cardigans and Swatch watches.
1112 N. Ashland Ave., 773-252-6996, koko-rokoko.blogspot.com
1112 N. Ashland Ave., 773-252-6996, koko-rokoko.blogspot.com
Lulu's at the Belle Kay
The emphasis here is on costume jewelry—all arranged in the center of the store—but the bordering racks deserve a look, too, since they're lined with vintage party dresses, many from highly coveted names.
3862 N. Lincoln Ave., 773-404-5858, lulusbellekay.com
3862 N. Lincoln Ave., 773-404-5858, lulusbellekay.com
Merz Apothecary
Truly old-world (it's been around since 1875), Merz stocks an intensive array of hard-to-find beauty labels, like 4711 (the world's first cologne) and Badger.
4716 N. Lincoln Ave., 773-989-0900, smallflower.com
4716 N. Lincoln Ave., 773-989-0900, smallflower.com
Morlen Sinoway Atelier
Occupying a garage-like, sun-drenched corner in the Meatpacking District, this looks like a gallery at first glance. Closer inspection reveals paper-thin, bright orange serving bowls and baskets from Mali.
1052 W. Fulton Market St., 312-432-0100, morlensinoway.com
1052 W. Fulton Market St., 312-432-0100, morlensinoway.com
P.45
This was one of our favorite boutiques in the country when Lucky launched more than a decade ago: It's still spot-on, offering labels like Winifred Grace, Lizzie Fortunato Jewels and 3.1 Phillip Lim.
1643 N. Damen Ave., 773-862-4523, p45.com
1643 N. Damen Ave., 773-862-4523, p45.com
Penelope's
Slightly retro, preppy standards by labels like A.P.C. set the tone here—while checkboard floors and midcentury-modern fixtures contribute to its schoolhouse vibe.
1913 W. Division St., 773-395-2351, shoppenelopes.com
1913 W. Division St., 773-395-2351, shoppenelopes.com
P.O.S.H.
Hotel silver, historic Queen-emblazoned ashtrays from the U.K. and a smattering of ephemera add up to P.O.S.H.'s enduringly great Parisian-flea-market feel.
613 N. State St., 312-280-1602, poshchicago.com
613 N. State St., 312-280-1602, poshchicago.com
