Waldorf Astoria Chicago

Natty riposte to the city’s more prim and proper five stars. To be sure, its deco inspired structure is adorned with stylistic cues from none other than Coco Chanel; and the vibe is decidedly au courant all around. Sleek (and big) rooms start at 614 sq. ft., and the stylish Astoria Suite comes with a fireplace and fully furnished terrace. Saunter elegantly on up to the second floor Bernard’s Bar for a sophisto evening of classic cocktailing. Elysian Spa is acknowledged as one of the best in the nation, so be sure to book ahead.

Thompson Chicago

Posh Gold Coast location means power shopping ladies mix with new gen media set. Fittingly, Nico Osteria and Salone Nico offer a more sophisticated seeing and being seen over refined antipasti and Italian inspired cocktails. Taking it upstairs means typical Thompson unflashily styled rooms, some with fab lake views.

Public Hotel

Debut of Ian Schrager’s “downmarket luxe” hotel brand. Nestled in posh Gold Coast, overrides Ace’s hipster cliches, instead does affordable chic without the wifi lobby rates. Rooms are comfy, simply stylish. Pump Room resto is groovy reboot of Chi-town legend, with Jean-Georges now at the helm – has generated new scene unto itself. Ian does it again.

Fig & Olive

Gold Coast branch mimics breezy chic of NYC originals – like dining in fancy furniture showroom. 10,000 sq. ft. spread over two unique indoor spaces, plus lovely, verdant terrace. Poshie brunch is rather a scene, over crab crostini, Provencal carrot & Thyme soup and truffled mushroom scrambled eggs. Gravitate to raw bar and superb fish dishes (to wit, Lake Superior whitefish papillote) at dinner time. Exquisite list of wines by the glass. Really quite fabulous.

Moncler

Moncler’s Gold Coast outpost brings a touch of Haute-Savoie chic to the WIndy City. The Gilles & Boissier-designed space embraces alpine charm with carved wood paneling and floral motifs, the perfect setting for the label’s space age-meets-preppy puffy jackets, which are all the rage with everyone from posh skiers to hip-hop royalty. The Chicago shop stocks Moncler’s full range of lines, from Moncler V to Moncler Grenoble, a reference to the Rhône-Alpes city where the label was founded in 1952. 

Forever 21

Fast fashion gets mega: Times Square flagship rocks four floors of tween faves and bargain frocks. Pretty much every look you can think of, trendy and tacky alike. Choose from 121 changing rooms to check your fit. H&M’s cheaper, American-born counterpart is hit and miss with selection, but sifting through overwhelming mass of patterned sundresses and printed blouses is all worth it when you find that sweet $38 cocktail dress that almost passes for D&G.

American Apparel

Founded in L.A. in 2003, hipsters flocked to work within the white-lacquered walls of American Apparel, hawking their rainbow of basics, and looking the other way when their friends swiped a hoodie. Downtown model-wannabe party kids stooped to employment in the hopes of being featured, scantily clad and compromisingly positioned, in their ubiquitous adverts. With the novelty worn off (and security tightened), the store’s become the alternative next generation of Gap: you can’t walk into a bar without seeing someone sportily sporting the cheaply-priced, sturdy duds. Started questionable trends from the sweatband headband to glittery leggings. Recently started selling upmarket California-inspired vintage too.

Lacoste

Ralph Lauren’s predecessor. Sweatervests and argyle are constants. Polo dresses and slimming cable knits for women. Tasteful oxfords and multi-color polos for men. Lightweight, breathable fabrics in all garments. Stays true to its roots with a tennis sportswear collection for men, women, and children. But the crocodile logo comes at a price.

Kate Spade

IN PREVIEW. Conservative Cape Cod totes, clutches, and shoulder strap bags done in bold stripes, patterns, and polka dots. Traditional heels ideal for weekend dress-up days and strolling around the office. Stationery and home accoutrements to flaunt Kate Spade lifestyle, reminiscent of ‘50s societal ideals—perfect mother, hostess, wife, woman.