Athene

North Shore elegance just got a dose of downtown edge. Opened last fall, Athene defies simple characterization. You can find anything from elevated basics by Humanoid to slim-yet-rugged camo pants by Nili Lotan ($375, pictured), and even more fanciful pieces from designers like Dodo Bar Or. 837 Elm St., Winnetka, 847-441-1918

Luxury Garage Sale

A rigorous multipoint authentication process at this impressively stocked mini-chain ensures you’re getting Gucci, not Bucci. 1658 N. Wells St.; 900 N. Michigan Ave.; luxurygaragesale.com

Sprout Home Kitchen & Table

Don't let this chic store’s name fool you—kitchens and tables are just the beginning. Yes, you can find uncommonly cool place settings and chef-quality cookware, but this sister shop to Goop-endorsed Sprout Home also stocks handwoven rugs, small-batch soaps, art-inspired blankets, fine linens, and giftable garden kits. 744 N. Damen Ave., sprouthome.com

Dearborn Denim & Apparel

A good pair of jeans is hard to come by. But it’s easy to find a perfect fit with this Hyde Park boutique’s made-in-Chicago line, which consists of just a few no-frills styles. A salesperson will measure you and hem your jeans on the spot, so you can walk out looking like the king or queen of cool. From $59. 1504 E. 53rd St., dearborndenim.us

Martha Mae

Every object in this treasure box of a shop in Andersonville—pens, sketchpads, scissors, you name it—feels like a work of art, thanks to owner Jean Cate’s insistence on exquisite design. Pick up a wooden box of paints, or browse the original sketches, frameable Japanese papers, and art books. 5407 N. Clark St., marthamae.info

North Avenue Collective

The priority at this Humboldt Park shop is quality, not irony or trends. That means tasteful vintage furniture, one-of-a-kind objets d’art, plus hip old-school clothing. 2511 W. North Ave., 312-883-2655