2. Add conversation pieces
We’ve all been there before: about 10 minutes into a first date and you’re awkwardly commenting on the bar’s zany décor or memorizing each word of the restaurant’s menu. Why? Because what else are you supposed to talk to a virtual stranger about? Luckily, you can kill two birds with one very stylish stone by sporting a garment or accessory that has a story. “If he’s wearing something that really matters to him — like his grandfather’s watch — those pieces always make for an awesome story,” said Hannah Orenstein, a writer for Seventeen.com who was previously a matchmaker for Tawkify, New York’s elite dating service. So go head, dear reader: Accessorize with that heritage timepiece or that luxe tie you scored from your European getaway. Not only will you look good, you’ll also be able to create some extra small talk.