When in doubt, a dressier shoe is the best option. While oxfords are best saved for suits and suit separates, a Chelsea boot or a derby shoe, for example, will work with dark-wash denim or chinos (if you insist). A canvas sneaker is acceptable for a more laid-back date, but dont pull out your old, tattered sneakers.

What shoes should I wear on a first date?

Dress and sneakers always! It keeps you comfortable and can show your personality. Personally, I love just a great-fitting retro or plain tee and a killer heel, fun sneaker, or statement bootie. For first dates, its more about the little details.

Is it OK to wear sneakers on a first date?

You can wear sneakers with anything, and on basically any first date-night occurrence. Sneakers and well-fitting jeans is also a no-brainer—just throw on a slinky sweater, camisole, or button up and youre at once put-together and low-key.