Style Guide

Light blue suit trouser hems with a clean break over dark brown penny loafers on a marble floor

Penny Loafers With a Suit: When It Works and How to Get It Right

Penny loafers and a suit is a modern, relaxed pairing, at the right event. Here's when it works, how to match colors, and how your trousers and socks should look.

Rolled dark denim hem and bare ankles with brown penny loafers on a wooden floor

How to Wear Penny Loafers With Jeans (5 Looks That Work)

Penny loafers with jeans is one of the easiest smart-casual outfits there is, if you get the fit and the hem right. Here's how, with 5 looks.

Men's penny loafers in brown, dark brown, tan, black and green suede-look finishes on a walnut floor

Penny Loafers for Men: How to Wear Them in 2026 (10 Outfit Ideas)

Penny loafers are the easiest smart shoe a man can own. Here's what they are, how to wear them with or without socks, and 10 outfits that work in 2026.