Walking into this floral boutique offers a breath of fresh air, literally. Far from your average florist, Elizabeth Cronin decks the space in everything from wild flowers to extraordinary succulents, mixed in with home decor à la faux stuffed moose heads and citrus-scented candles. 1935 W North Ave between Damen and Winchester Aves (773-782-0680). El: Blue to Damen. Bus: 50, 56, 72. Mon–Sat 10am–7pm; Sun noon–4pm.
This sample-sale-turned-brick-and-mortar-boutique features sample and overstock apparel marked 40 to 90 percent off original retail prices. Just imagine: You can walk away with a bag full of goodies by designers like Rory Becca, Alice Roi and Ulla Johnson without a guilt complex. 2016 W Concord Pl between Damen and Milwaukee Aves (773-276-0905). El: Blue to Damen. Bus: 50, 56, 72. Thu, Fri 11am–5:30pm; Sat 11am–5pm; Sun noon–5pm.
This charming shop is known for stocking tiny designer labels, many from New York’s hippest enclaves. The standout line in the boutique, though, is co-owners Kelly Whitesell and Elizabeth Del Castillo’s, which is also named Eskell and was featured at last year’s Fashion Focus. The duo has also recently started organizing designer sample sales. 1509 N Milwaukee Ave between Honore St and North Ave (773-486-0830). El: Blue to Damen. Bus: 50, 56, 72. Tue–Sat 11am–7pm; Sun 11am–5pm.
Lacy thongs, silk camis and sex toys aren’t the only reasons to stop by this upscale lingerie shop. This place also offers pinup photography and hands-on classes to help you design your own pasties or improve your man-handling skills. 2131 N Damen Ave between Charleston St and Dickens Ave, (773-235-1234). El: Blue to Damen. Bus: 50, 56, 72. Mon–Sat 11am–7pm; Sun noon–5pm.
Lindsey Boland’s boutique showcases original handmade clothes and accessories from about 50 up-and-coming designers (such as Suzabelle, Alisha Alderman and She-Bible), half of them local—including selections from her own line, Superficial Inc. 1951 W Division St at Damen Ave (773-342-0093). El: Blue to Division. Bus: 50 Damen, 70, Division. Tue–Sat 11am–7pm; Sun noon–5pm.
Shopping this wide, airy space is like walking the aisles of a pristine gallery of fantastically stylish men’s and women’s clothing, modern art and architecture books and housewares. Look for breathtakingly creative (albeit exceedingly pricey) designs by Opening Ceremony, Nice Collective and Comme des Garcons to whisk you from dinner at Rodan to an avant-garde photography opening. Sign up for the shop’s mailing list to stay posted about occasional events showcasing local artists. 1529 N Milwaukee Ave between Honore St and Damen Ave (773-772-0002). El: Blue to Damen. Bus: 50, 56, 72.Tue–Sat 11am–7pm; Sun noon–6pm.
This new, off-the-beaten-path vintage shop stocks plenty of looks from the “Me Decade” and beyond, but ten percent of the merchandise is new items by local designers such as screenprinted T-shirts and scarves by Kiyomi Kimble. All resale items are under $100, including a large selection of cowboy boots. 1112 N Ashland Ave at Haddon Ave (773-252-6996). El: Blue to Division. Bus: 9 Ashland, 70 Division. Mon–Sat 11am–7pm; Sun noon–6pm.
Lenny & Me
Vintage and thrift attire (and occasional housewares) share the floor space in this rather sprawling resale store, where you can buy, sell or trade. Keep an eye out for steals like a gently worn Diane von Furstenberg wrap while you size up the latest selection of polyester frocks and locally designed charm-adorned jewels. 1463 N Milwaukee Ave between Honore St and Evergreen Ave (773-489-5576). El: Blue to Damen. Bus: 50, 56, 72. Mon–Sat 11am–7pm; Sun 11am–6pm.
This local womenswear designer specializes in tops, bottoms, jackets and dresses featuring unconventional cuts, unfinished hems and minimalist colors (think black, white and, uh, tan). She also sells complimentary pieces by other up-and-coming designers in her clean and simple shop. 1872 N Damen Ave between Moffat and Cortland Sts (773-252-1888). El: Blue to Damen. Bus: 50, 56, 72. Mon–Sat 11am–7pm; Sun noon–5pm.
Joe Lauer and Jena Frey’s boutique carries cute, uniquely cut garments, shoes and accessories with a touch of mod (think Grandma meets the Beatles) for men and women. The shop is one of the few in the city to offer a large selection of French cult label APC. 1913 W Division St between Wolcott and Damen Aves (773-395-2351). El: Blue to Division. Bus: 9 Ashland, 70 Division. Mon–Sat 11am–7pm; Sun noon–6pm.
The ladies who launched the first Renegade Craft Fair a handful of years ago took the fair to the next level by opening this full-scale boutique. Look for fair favorites such as twee plush pastries, stationery goods and screenprinted tea towels. 1924 W Division St at Winchester St (773-227-2707). El: Blue to Divison. Bus: 50 Damen, 70 Division. Daily 11am–7pm.
Even if you don’t have the cash to drop (and you’ll need plenty of it, here), stop by this tactile store for inspiration alone. Sculptural, multilayered clothing hangs from the racks like objects of art among the French antique fixtures adorning the walls. 2108 N Damen Ave between Charleston St and Dickens Ave (773-278-6150). El: Blue to Damen. Bus: 50, 56, 72. Tue–Sat 11am–6pm; Sun noon–5pm.
Shoppers get an education on each collection at this boutique. The rustic space features racks of clothes separated by designer, each accompanied by a wall-mounted biography. So you’ll learn that Liz McClean’s floaty tunic dresses ($315) are hand-dyed in Brooklyn, and that Collection K’s soft alpaca sweater coats ($258) are a hit in their native Paris. 2035 N Damen Ave between McLean and Dickens Aves (773-489-1311). El: Blue to Damen. Bus: 50, 56, 72. Tue–Sat 11am–7pm; Sun noon–5pm.
Saint Alfred is the patron saint of learning, and the expert staff at this new Wicker Park boutique will gladly school you on the latest styles. Although it doesn’t offer customization, St. Alfred’s features limited-edition and collaboration lines such as Yohji Yamamoto for adidas and Japanese import Visvim. 1531 N Milwaukee Ave between Honore St and North Ave (773-486-7159). El: Blue to Damen. Bus: 50, 56, 72. Mon–Sat noon–8pm; Sun noon–6pm.
Infusing the School of the Art Institute of Chicago’s fashion-as-art approach into classic, tailored looks, Serpico’s line reflects an interest in juxtaposing details like unfinished raw silk edges and fringed trim with fluid lines. 1514 N Ashland Ave between Le Moyne St and Pierce Ave (773-252-5940). El: Blue to Division. Bus: 9, 56, 70, 72. Mon–Fri 11am–7pm; Sat 11am–6pm.
Owner Liz Meyer, a fashion stylist for Aerosmith, has compiled a beautiful collection of day wear and formal attire. Standouts include striped taffeta cocktail dresses from the 1950s, along with a heavy focus on Vivienne Westwood. The men’s collection includes suit jackets and trousers, plus shirts, jackets and suits from Steven Tyler’s personal collection. 1755 W North Ave at Wood St (773-235-5797). El: Blue to Damen. Bus: 50, 56, 72. Tue–Fri 11am–6pm; Sat noon–7pm; Sun noon–5pm.
Little ones can get into the graphic T-shirt craze thanks to the racks full of mini versions (sizes newborn to 12 years) of this popular company’s screenprinted merchandise that’s designed and then voted for online by the public. 1905 W Division St at Wolcott Ave (773-698-7042). El: Blue to Division. Bus: 9 Asland, 70 Division. Mon–Sat 10am–7pm; Sun 11am–5pm.
Una Mae’s Freak Boutique
The main floor here houses a hipster-chic selection of menswear and womenswear (skinny jeans, jumpers and adorable jackets) with a vintage flair, but wind your way up the spiral staircase to the second floor to find the real-deal moth collectors. Don’t miss the jewelry case, a treasure trove of cheap costume jewels like faux gold bangles and lockets. 1528 N Milwaukee Ave between Honore St and North Ave (773-276-7002). El: Blue to Damen. Bus: 50, 56, 72. Mon–Fri noon–8pm; Sat 11am–8pm; Sun noon–7pm.
Skip the latest, full-price selections from Diesel, Obey and more, and head straight for this hip clothing shop’s discount racks. There are always at least four sale racks in the shop, full of designer duds still wearable this season—at a fraction of their original prices. 1941 W North Ave between Winchester and Damen Aves (773-342-0500). El: Blue to Damen. Bus: 50, 56, 72. Mon–Sat 11am–8pm; Sun 11am–6pm.