4 Cute First Date Ensembles to Meet a Guy Who’s Wearing a T-shirt and Sneakers

This Stella Gingham Open Shoulder moment is the perfect outfit to meet your date, a guy wearing an overstretched t-shirt and dirty sneakers, for a quick drink or dinner and a movie. Your date, a guy wearing a t-shirt and sneakers he definitely bought over four years ago, will appreciate the time you took to assemble this look that says you’re cute and feminine but also still “totally chill” and down to smoke a blunt while the game is on. Pairing this top with white ankle boots gives your look a little edge that will let your date, a guy who absentmindedly threw on a t-shirt that was definitely closest to the bed, know that you like taking risks and even rode on the back of a moped in Italy one time.