What Should I Wear to…?: Chicago’s Rooftop Bars

Chicago has some top-notch rooftop bars. From The Roof at The Wit Hotel at State and Lake, to Whiskey Sky at the W Hotel, to Vertigo Sky Lounge at the Dana Hotel, to C-View at the Affinia Hotel, to The Terrace at the Peninsula Hotel, there is no shortage of high places to get your drink on.

Haute bars call for haute couture. The first thing to remember if you are going to a trendier rooftop bar is to ditch the denim. This is summer in the city, so go with something flirty and feminine. This dress from Marchesa is the perfect LBD for an RTB (rooftop bar).

Pair it with these gold sparkly peep toe heels by Badgley Mischka. If you are out under the stars, you might as well glitter with them.

Add this Diane von Furstenberg clutch with gold hardware to modernize the LBD.

Throw on a few thin gold bangles or a chunky structured gold ring to complete the black-and-gold look. Wear your hair in soft waves to match the ruffled organza dress, and I promise you that nobody will be taking advantage of the RTB skyline views. They will be too busy staring at you.