14931 Lakeside Row, Lakeside
Along Chicago’s nearby Red Arrow Highway, a don’t-miss spot is AP Shop, a store owned by former Barneys visual director Ariane Prewitt and packed with a constantly changing display of finds: linen bags and handmade leather shoes from Mexico, cotton apparel and home goods from India, and pieces from independent American designers like Jasmin Shokrian.
Apartment Number 9
1804 North Damen Ave
As enticing as the brick-and-mortar shop, this new e-commerce site for men makes it easy to browse the likes of Maison Martin Margiela, Billy Reid and Relwen.
212 West Chicago Avenue
Occupying a large unmarked gallery space on the near North Side, this minimalist boutique offers womens wear from brands like Céline, Balenciaga, Martin Margiela and Roland Mouret.
Cityblue Apparel & Denim
1444 North Wells Street
It’s a rare day when the fashion flock strays from the city to the ‘burbs, but CB Boutique will lure even the most stalwart city dweller northward. Its Lake Forest space is filled with designer labels for men and women, including Theory, Halston and Simon Spurr.
900 Michigan Avenue
The new Magnificent Mile store specializes in sporty style: Y-3, Adidas by Stella McCartney, Splits 59 and Newton running shoes—the answer to pre-Pilates, après-spin and everything in between.
43 East Ohio Street
Star chef Mario Batali recently opened up an outpost of his massive Italian foodie haven. The 63,000-square-foot space hosts eight restaurants, a brewpub, a butcher and a special grocer.
46 East Oak Street
Gallery Aesthete brings men an avant-garde space filled with offerings Comme des Garçons, Rick Owens and Ann Demeulemeester mixed in with art objects.
Haberdash Bespoke and EDC
607 North State Street
Tailored and luxury sportswear is the focus at Haberdash Bespoke, with brands like L.B.M. 1911 and Southwick. Next door, at Haberdash EDC, casual, heritage-brand clothing from Gitman Bros. Vintage, Red Wing Shoes and Baldwin Denim mixes with accessories and apothecary goods from lines such as Filson and Rag & Bone—plus, there’s a barbershop that’s open five days a week.
15 East Huron Street
If you’re looking for high-quality goods, Ikram is the place to go. The first floor is laid out with designer women’s clothing, and the second floor features an exclusive selection of home goods and a gallery focused on local artists. Plus, if you work up an appetite while shopping, you’re in luck—Ikram has a café right in the store that specializes in farm-to-table cooking. The boutique attracts lofty locals like Michelle Obama, Desiree Rogers and Mellody Hobson.
47 East Oak Street
No outsourcing here: “Made in the U.S.A.” is the theme of the classically cool men’s shop. Bespoke footwear made in Chicago by Oak Street Bootmakers and Ebbets Field Flannels from Seattle are on offer at this Gold Coast store.
Rosemont’s Fashion Outlets
5220 Fashion Outlets Way
A one-stop shop for the fashionable, the frugal and the highbrow, Rosemont’s Fashion Outlets of Chicago is a posh new outlet mall of luxury stores, including Gucci, Brunello Cucinelli and Hugo Boss.
325 West Ohio Street
Brian Spaly created Trunk Club out of frustration with the boutique shopping experience. With the help of a stylist, via phone or email consultations, Trunk Club FedExes clients eight to 10 items; after trying things on at home, they can ship back returns.
34 East Oak Street
VMR (Vintage, Modern, Resale) is a by-appointment designer resale boutique, a curated closet of one-of-a-kind pieces curated by Mark Gill from Chanel, Fendi, Oscar de la Renta and more.
110 East Oak Street
The Zaharoff flagship comes with a large-scale mural—and tailored suits, ties and shirts for the classic gentleman. The modern American aesthetic is rooted in the simple elegance of the suit.