The Best First Date Outfits That’ll Make You Feel Confident & Cute

Oct 27, 2023

All products and services featured are independently chosen by editors. However, StyleCaster may receive a commission on orders placed through its retail links, and the retailer may receive certain auditable data for accounting purposes.

If your first date is an outdoorsy activity like hiking a trail, riding bikes, jogging, or attending a workout class, you’ll want to wear the cutest of athleisure à la Hailey Bieber and Lori Harvey. Bike shorts and leggings are cute but practical options that can easily be paired with a matching crop top, a comfy graphic tee, or an oversized hoodie. Pair them with cool sneakers, crew socks, and oversized sunnies, and you’ll be ready to go.