We know you'll do anything you can to feel comfortable on a first date (and no, we're not talking about multiple cocktails). Chicagoans know that first dates happen even when the weather isn't sundress-appropriate, but, sadly, layers don't often flirt the way we want them to. Lo and behold, though, we recently spotted an outfit that takes care of all your first date needs, from looking completely cute to being practical weather-wise. Anything we can do to help our readers find love is simply our pleasure. If we knew how to make your date witty, charming, and on-time, trust us, we'd do it.
Siouxie Leather Biker Jacket by Lot78, $860, available at Net-A-Porter. Alba Mini Skirt, $145, available at All Saints. Heart Suspender Sheer Tights, $17.93, available at ASOS. Kiss Baby Cross-Body Bag by Rebecca Minkoff, $195, available at Endless. Mambo nail polish by Essie, $8.00, available at Beauty.com.