ASOS Tassel Loafers in Suede
Buy It Now at ASOS, $74

Velvet slippers are little too precious, while penny loafers are way too casual for the occasion. Enter the tassel loafer. Somewhere between dressy and casual, they're also a decent conversation piece if you pair them with the right, dressed-up kit. It could be what sets you apart from the legions of bros out and about, and might help you seal that midnight smooch.