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

What A Feeling Midi Dress (Free People, $168)

This oversized dress paired with black boots is the PERFECT ensemble to meet your date, a guy wearing a T-shirt and sneakers. This look tells a story of someone that is fun and loose but also someone who can put together a cheeseboard in 10 minutes. Your date, a guy who put no thought into his outfit, will appreciate the effort you put into Ubering from store to store in order to curate this look that says both “Bohemian girl” and “fun hang”.