For slip-on shoes—whether it’s a pair of loafers, penny loafers or boat shoes—a really fitting pair is the most important consideration; as unlike a pair of lace-ups, you can’t tighten slip-ons
As for styling, going sockless is considered the go-to method to wear slip-ons. If you choose to go this route, then mind
the gap: make sure your trousers don’t sag over your shoes and instead taper in near the ankle, leaving a slight gap.
For the trousers themselves, linen or chinos are best for hot to mild weather, and wool or denim are the definite fall/winter choice.
Deciding to go with socks, anyway? Then match them to your trousers. Contrasting socks can work, but that takes some real guts.
This article first appeared in DA MAN Style Fall/Winter 2015. Go here to get a copy of our back issues.