Shop the look: 1. River Island cami, $52; riverisland.com 2. Gorjana collar necklace, $75; revolve.com 3. Zara double-breasted waistcoat, $50; zara.com 4. Adam Lippes pants, $890; net-a-porter.com 5. Coach crossbody, $595; coach.com 6. Paul Andrew heels, $745; modaoperandi.com
Afraid you'll miss the cutoff for happy hour? Well, we can't let that happen, because it is Wine Wednesday. The goal is to piece together an outfit that works for both—one that says, "I'm a professional" during the 9-to-5 grind, but doesn't read stuffy or rigid once you start sipping on a glass of Bordeaux. The foundation begins with a beautiful pair of wide-leg pants in a rich color (say, the shade of red you'll be drinking later) with a lace-trimmed velvet cami (sexy, but not overtly so). But eliminate any hint of anything that's not completely office-friendly with a sharp double-breasted waistcoat, a pair of basic black pumps, and a sensible tote. Once you clock out, swap your heavy holdall for a whimsical floral-adorned purse, and you're all set. And if you really want to keep the night going, shrug off your structured vest for added allure.
—Market by Ann Jacoby