The bricks-and-mortar outpost of the famous crafts fair of the same name, this tiny store is packed with handmade things, including adorable stationery and cute canvas totes.
When it comes to a subtly bohemian aesthetic—served up via Gary Graham's asymmetrical dresses and exotically tinged jewelry—Robin Richman always gets the city's top honors.
It may be helmed by a J.Crew veteran, but there's nothing preppy about Roslyn: Romantic one-off tops by Luxury Jones hang next to Christina Hattler dresses.
This new below-ground spot is a street-inspired concept shop: Christopher Kane T-shirts, Alexander Wang sunglasses and Dee and Ricky Lego brooches abound.
Located just off the primary downtown shopping stretch, Sarca is well worth seeking out: Avant-garde Vivienne Westwood dresses mingle with Grey Ant denim trousers and spiky Camilla Skovgaard heels.
Antique 19th-century wedding dresses get top billing here, but the real pull is the racks up front, full of gorgeous, big-event gowns.
Sprawled out on the fifth floor of one of Michigan Avenue's main malls, this spot feels like a well-kept secret: Coffee-table books, rare European beauty products, cashmere sweaters and a smattering of cool antiques set the eclectic tone.
At this store devoted to all things garden-related, you should definitely pay special attention to the wildly cool (and packable) terrariums, peopled with hilarious miniature figurines.
There's an intensive array of Missoni home goods at this long-standing accessories emporium, but it finds fitting company with the equally luxe-feeling (but well-priced) handbags by Carla Mancini and woven Presh bracelets.