Wristwatches
Astor + Banks
Self-styled “watch nerd” Andrew Perez caught the bug while serving in the army and has been designing and hand-assembling timepieces since 2012. His limited-edition watches start at $1,250, feature Swiss quartz movement, and sell out quickly. In the works: a self-winding model with a mint-green dial. 320 N. Damen Ave., West Town, astorandbanks.com
New Home Accessories Shop
Eskell
Making your apartment look like Instagram’s most bookmarked houses is easy when you’re choosing from the modern-boho furniture, lamps, textiles, ceramics, and shelf fillers in Eskell’s massive upgraded store, which opened earlier this year. 2029 N. Western Ave., Bucktown, eskell.com
New Gallery Row
Chicago Avenue from Ashland to Wood
This quiet stretch is the city’s new capital of highbrow culture. In addition to the iconic Rhona Hoffman Gallery (pictured), there’s a lively second-floor complex at 1709 West Chicago Avenue boasting four consistently innovative spaces — Western Exhibitions, Document, Volume Gallery, and Paris London Hong Kong — that both showcase established artists and uncover emerging stars. West Town
Tween Shop
Frankie’s on the Park
You really can have a shopping trip free of eye rolls with your 9- to 12-year-old. This Lincoln Park shop carries brands that are trendy, not trashy, such as flowery Me.N.U. rompers, distressed Blank NYC jeans, and cozy Autumn Cashmere pullovers. Tip: Bring in last year’s gear for a studded update at the Bling Bar. 2322 N. Clark St., Lincoln Park, frankiesonthepark.com
Rugs
Reza’s Rug Gallery
Call ahead and ask Reza Heidari to pull the sizes and colors you want from his soaring piles (and piles and piles) of antique handmade Turkish, Chinese, and Persian rugs, all immaculately restored. Or drop in and sip tea while you wait. 2131 N. Southport Ave., Lincoln Park, rezasruggallery.com
Vintage Store
Knee Deep Vintage
This airy shop packs in a century’s worth of beautifully curated new-to-you duds, arranged on the racks in a browsable rainbow. Outfit yourself head to toe in throwbacks, or unearth the perfect preloved bag or pair of jeans. 1219 W. 18th St., Pilsen, kneedeepvintage.com
New Bookstore
The Dial Bookshop
New bookstores don’t pop up often, but a new used-book store in a beautiful space with an impeccable selection by local authors? A rare bird indeed. 410 S. Michigan Ave., Loop, dialbookshop.com
DIY Duds
The Garment Creative
Designing your own clothes while drinking wine sounds like a recipe for regret. But these stylists will ensure you pick fabrics and trims that look profesh when they get to you. 2124 W. Division St., West Town, thegarmentcreative.com
Wedding Boutique
Honey Bridal
There’s plenty of cascading tulle at this year-old shop — but also black sequins, exposed gold zippers, and other idiosyncratic touches for the bride who’s more rock star than fairy princess. Gowns range from $1,800 to $8,000, but most fall in a sweet spot between $2,500 and $3,500. 5135 N. Clark St., Uptown, honey-bridal.com
Bead Shop
String a Strand on Wells
Consider a visit to this store a drug-free antidepressant: The Technicolor beads draped on the walls and filling the tables are a guaranteed mood lifter. Take a class, or design a bauble on your own. 1361 N. Wells St., Old Town, stringastrand.com
Place to Rent Fancy Clothes
By: Fashionaholic
Women sign up on years-long waiting lists to buy an Hermès Birkin bag. Now you can get a loaner. Blogger Janet Mandell is opening up her closet (and bringing in items from New York City) in what amounts to Rent the Runway on steroids: limited-edition Gucci bags, glittery Roberto Cavalli cocktail dresses, and citrus-bright Chanel suits, all of which you can borrow for between $250 and $600. $1,000 for a one-year membership (but you can try it once before joining), plus rental fees. byfashionaholic.com
Smackdown!Ritzy Shopping District
Oak Street
Michigan Avenue
| High-end flagships | Chanel is moving there from its Mag Mile digs, joining Prada, Dolce & Gabbana, Tom Ford, and more. | Burberry, Cartier, and Gucci call it home. But so does Forever 21. |
| Fast-fashion high point | Cos, H&M’s design-forward sister store | Punchy Japanese basics brand Uniqlo |
| Chances of getting elbowed by tourists | Low. Shopping bags on your arms three-deep, you’ll still glide down the sidewalk. | As high as the odds they’re heading to get deep-dish pizza |
| Sceniest eats | The Esquire Champagne Room, where ladies in towering stilettos daintily nibble caviar | RL, where status-conscious Chicagoans have standing reservations |
| Number of stores where you can buy cellphones | C’mon | Five |
Winner:Oak Street. It may be only a block, but it’s leagues longer than the Mag Mile in style.
Lingerie Store
Underthings
This teeny boutique is stacked with stylish bralettes, sweet sets, and silky nighties in macaron-colored mesh and lace. 804 W. Webster Ave., Lincoln Park
Women’s Boutique
Space 519
The new digs have the same cool-girl labels as before. But now you can also grab lunch in a breezy café. 200 E. Chestnut St., Gold Coast, space519.com
New Men’s Boutique
Cowboys and Astronauts
A nearly life-size fiberglass astronaut keeps watch at this newcomer, which is geared in equal measure toward bearded, flannel-wearing types and those who prefer their shirts sharp and starched. Selling brands like Topo Designs, Areaware, and Son of a Sailor, the boutique supplies a thoughtful mix of clothing and home goods. 1478 W. Summerdale Ave., Andersonville, cowboysandastronauts.com
Racket Shop
Strings Attached
Squash, tennis, and pickleball aficionados flock to this beloved store (which now has a location in the burbs) for its quick turnaround and top-notch customer service. The team will match or beat competitors’ prices and let you try any stick for $10, which goes toward the price if you buy. 1369 W. Fullerton Ave., Lincoln Park, and 1910 S. Arlington Heights Rd., Arlington Heights, stringsattachedstore.com
Craft Market
Cheap Thrills at Emporium
Twice a year, Chicago’s hippest designers and boutique owners meet at an arcade bar to day-drink, play Pac-Man, and sell discounted jewelry, clothes, beauty treats, and housewares. Crash this party. 2363 N. Milwaukee Ave., Logan Square, @cheapthrillschicago on Instagram