Loafers

A penny loafer has a plain strap across the vamp with a small cut-out slot. A tassel loafer replaces that strap with lacing that ties into two tassels. The penny is the more versatile of the two and the easier one to dress down.

Yes, and it is one of the better pairings. A dark brown or suede loafer with a straight or wide leg jean reads far more considered than a sneaker without looking formal. Keep the hem short enough that the shoe is visible.

Leather loafers stretch about half a size across the width as they break in, but they do not lengthen. Buy snug across the forefoot and true to length. Suede gives slightly faster than calf leather.

Either works. No-show socks keep the interior from wearing out, which matters on unlined pairs. Visible socks with a wide leg trouser have become the more common look and are worth trying.

Anything with a welted construction, which includes the Paraboot models we stock. Hand-sewn moccasin constructions like Sebago and Padmore & Barnes can usually be resoled by a good cobbler as well, though it is more involved.