Done right, loafers can feel effortless.

The shoe once associated with prep schools, finance guys, and old-school tailoring has become one of menswear's most versatile pieces. These days, loafers are just as likely to appear with baggy jeans and a vintage T-shirt as they are with a suit.
Part of that shift comes from the way men are dressing now. If you haven't noticed, tailoring has relaxed. Heck, even sneakers aren't the automatic answer they once were. And loafers offer something many shoes can't: a clean look without looking overly dressed up.
Choose the right pair first: If you're worried about looking too formal, start with edgy loafers rather than sleek dress versions. Lug soles, suede finishes, and slightly rounded shapes instantly feel more relaxed than shiny leather styles with razor-sharp silhouettes.
Wear them with denim: One of the easiest ways to remove any stuffiness from loafers is to pair them with jeans. A sample look can be washed straight-leg denim, a plain white tee, and a lightweight jacket. It's the formula celebrities like Jacob Elordi and Tyler, the Creator keep returning to.
Skip the skinny trousers: Slim trousers and loafers can quickly drift into office territory. Instead, pair them with relaxed pleated pants or wider-leg trousers. The looser silhouette feels more current and gives the shoe room to breathe.
Try them with shorts: It sounds unexpected, but loafers and shorts have become one of menswear's most reliable combinations. Look at Paul Mescal, who regularly pairs shorter shorts with loafers. The contrast between casual and dressy makes the outfit feel cooler.
Keep the socks visible: For years, the default advice was to go sockless. Today, visible socks often look quirky. White athletic socks, ribbed crew socks, or even subtle patterned pairs can make loafers feel more casual and contemporary.
Another tip? Loafers work best when the hem of your trousers hits cleanly above the shoe or breaks lightly over it. Too much stacking can look messy, while cropped trousers can sometimes feel overly styled. Aim for something relaxed and natural because that's always the vibe.

Sebastian Stan in Gucci at Nice Airport in France. Getty Images.

The How-To Guide for Wearing Loafers Without Looking Too Formal

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The How-To Guide for Wearing Loafers Without Looking Too Formal

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