Whatever becomes of Jennifer Aniston and Vince Vaughan, their high-profile courtship, carried out partly in his hometown of Chicago, has done wonders for the city's image as the Midwest capital of cool. While elegantly coiffed ladies stalk the big brands along Michigan Avenue, known locally as Magnificent Mile, the younger generation shop near their shabby chic homes in Lincoln Park and the adjacent, up-and-coming neighbourhood of Old Town. Walls of colourful bras lure self-assured bodies to Isabella Fine Lingerie (1101 West Webster Avenue, tel: 1 773 281 2352; www.shopisabella.com ). Fans of itsy bits by Cosabella and Woo pledge their eternal gratitude to owner Lauren Amerine, inspired by an Italian holiday to bring European lingerie to the boudoirs of America's conservative heartland. These days, however, some of her biggest sellers are the decidedly domestic little 'boy leg' panties by Honeydew (US$10). Nearly next door, Shop Girl (below; 1206 West Webster Avenue, tel: 1 773 935 7467; www.shopgirlchicago . com) spices local wardrobes with Indian paisley skirts from Basil & Maude (US$169) and stocks knee-high Minnetonka Moccasins (US$80), the Native American footwear made catwalk cool. Spruce up your teepee at Art Effect (934 West Armitage Avenue, tel: 1 773 929 3600; www. arteffectchicago.com). Imported Sven boot-clogs carry chic Chicagoans through brutal winters in style while Michael Aram's stainless-steel bowls (US$225) and sculptural cocktail shakers by Nambe (US$145) add a touch of bling. Shopper turned shopkeeper Gina Kulbeida moved Jolie Joli (1623 N. Damen Avenue, tel: 1 773 342 7272) to the outskirts of Lincoln Park and into a historic fire station two years ago but committed fashionistas make the pilgrimage without complaint. Though stacks of vintage-style Kowboy T-shirts (US$55) keep male arm-candy entertained, the fashion focus here is decidedly female. Ballerina-inspired baby-doll camisoles by Velvet (US$180) can be worn even when temperatures drop, thanks to bohemian chic knit wraps by Whim (US$225). Under the whimsical antique street-lamps that line the lanes just south of Lincoln Park, the hip modern boutiques of Old Town satisfy the sophisticated tastes of young mothers, who manoeuvre their imposing all-terrain baby Bugaboos with impressive dexterity. They stay creative by customising a new handbag or re-styling their unworn clothes (from US$50) at Eliana Lily Chicago (1628 North Wells Street, tel: 1 312 337 0999; www.elianalily.com ). Private parties here attract wannabe Miuccia Prada types longing to test their flair. Chandelier-lit and intimate, designer shoe salon Josephine (1405 North Wells Street, tel: 1 312 274 0359; www.josephineonline . com) stocks diverse looks, from Christian Lacroix's bejewelled open-toed evening sandals (US$665) to casual metallic trainers by Emma Hope (US$340). Boots may be the best part of this booty, particularly Tania Spinelli's silver buckle ankle boots (US$695) and Alexandra Neel's pointy-toed tassel boots in chocolate brown (US$950). Cross West Schiller Street to Etre (1361 North Wells Street, tel:1 312 266 8101; www.etrechicago . com), where denim dreams come true for those skinny enough to slide into Sacred Blue's Twiggy jeans (US$192) or Joe's Honey Jean (US$159). Dangerous is how some describe Sara Jane (1343 North Wells Street, tel: 1 312 335 1962). While the clothes don't necessarily spark trends, Bianca Nero wrap dresses (US$205) and tutti-frutti dresses by Single (US$260) will brighten anyone's wardrobe. Sky-high piles of sequined wife-beaters, flavoured neon-hued lip gloss and handmade coconut shell necklaces (US$125) make this friendly shop fun for a quick pick-me-up.