Brown Beefroll Crepe-Sole Penny Loafer
Buy It Now at Oak Street Bootmakers, $336

This preppy mainstay gets a facelift from the heads at Oak Street Bootmakers, throwing it on a lightweight crepe sole that's perfect for summer stunting, and when they get worn down you can definitely replace them with another sole of your choosing. The "beefroll" stitch at the sides and apron stitch at the back keeps things casual, so rock these with shorts, jeans, or anything really. Who says you can't wear them with a tank top or tee?