Chicago’s Oak Street, just off the main drag of the Mag Mile, is the city’s premier destination for designer finds.
Here’s a quick guide down this glamorous avenue and a few of its neighboring streets.
First stop: lunch (and parking).
You’ll need sustenance for your afternoon shopping expedition, so stop by this outpost in the Tremont Hotel that offers juicy burgers and surprisingly good salads. The best part? If you’re driving, you can valet park your car and leave it while you shop, a convenience that cannot be overestimated in this high-rent parking area. 100 E. Chestnut St., 312-587-8989
It doesn’t get any better than a complimentary personal shopper—take advantage of Barney’s extraordinary customer service, part of which includes associates “taking the guesswork out and putting the style in.” Everything about Barney’s is thoughtful and well-designed, playing off the store’s new architectural aesthetic—from the clothing displays to the virtual wonderland of beauty products in the lower level. It’s a modern, luxury experience you won’t soon forget. 15 E. Oak St., 312-587-1700
“We don’t advertise—people have to find us,” is this boutique’s telling—and accurate—motto. Customers really do seek out this store, and so should you, if just to admire the gorgeous merchandise. Stocked with the highest quality Italian cashmere sweaters, wide-brimmed hats, leather driving gloves and customizable crocodile and ostrich bags, Loro Piana is all about luxury. 39 E. Oak St., 312-664-6644
Housed in the old Barney’s space on the corner of Rush and Oak, the new Hermes store is stunning. The Hermes scarf is a classic, but we’re really loving the lightweight cashmere scarves for fall that are more affordable but just as beautiful. Hermes leather, from their belts to their boots to their bags, are investment pieces, but they’ll be ones you’ll have for years to come. 25 E. Oak St., 312-787-8175
Visit David Lampert at Lester Lampert to commission an exquisite, one-of-a-kind piece of jewelry expertly designed to your specifications. Lester is an inductee in the National Jewelers Hall of Fame and David is a graduate of the Gemological Institute of America. The service is amazing and the jewelry, divine. If you’re in the market for vintage, browse their thoughtfully edited selection. For the boys—whether you’re looking for that special holiday gift or trying to find the perfect engagement ring, your lady won’t be able to resist one of Lester’s sparklers. 57 E. Oak St., 312-944-6888
This boutique chain, a favorite nationwide, is known for finding and featuring up and coming designers along with the more established names. The eclectic collection has something for every style—fur-lined leather jackets, chunky knits, Herve Leger bandage dresses, Chloe bags, Sergio Rossi shoes and a small but fabulous selection of denim. Pieces are fashion forward but not overly trendy, so you can wear them for seasons to come. 40 E. Delaware Place, 312-640-2922
Chicagoans need boots—it’s a fact of winter. If the name Ugg conjures up the flat, sheepskin boot that became so ubiquitous a few years ago, visit their store and expand your horizons. The line now offers cute and affordable leather, suede and duck boots, plus non-boot styles like sneakers, sandals and slippers. Stock up on fashions, too, from their coat and sweater options. And if you’re still attached to the classic Ugg, look for the upcoming capsule collection designed in collaboration with Jimmy Choo. 909 N. Rush St., 312-255-1280