How to Wear Loafers: 10 Foolproof Ways to Pull Off the Shoes of the Summer

How do you wear loafers? That’s a little bit like asking how to eat rice. There are endless varieties of the essential slip-on shoes to choose from, from classic penny loafers and swanky bit loafers to daddish kiltie loafers and daddish sneaker loafers. And those multitude of options, in turn, are each versatile enough to service a wide spectrum of outfits—casual beach looks, everyday office ensembles, big-night-out formalwear, you name it. So whether you’re looking to suit up sans socks with your classic black Weejuns or hit the streets in half-calfs and Dr. Martens, we’ve rounded up 10 of the most stylish loafer moments of all time to help inspire your next major fit.

4 Superlative Loafers to Slip Into

• The Classic Pick: Tod’s Leather Loafers, HK$7,600
• The Sporty Pick: Dior Combat Loafers, HK$8,200
• The Tassel Pick: Prada Brushed Leather Loafers, HK$9,250
• The Venetian Pick: Loro Piana Venice Walk Loafers, HK$6,700

The platonic ideal of an airport fit: elegant blazer, roomy trousers, comfy tee, and a convenient pair of loafers to slip on and off in the TSA line.

White loafers can be harder to pull off, but they work a charm with boldly-hued, disco-ready tailoring.

Black-tie shorts are a galactic-level swerve, but P’s chic studded loafers help lock things down nicely.

OK, let us now pay our proper respects to one of the most prominent and prodigious loafer wearers of our time: Tyler, the Creator. Here he is in his go-to Doc Martens with washed denim and a sick Fair Isle knit…

How do you cap off an impeccable alabaster ensemble like this one? With contrasting patent leather loafers and a rakish hint of bare ankle.

There’s a jumble of sporty-casual and dressy-formal elements at play here. The loafers cut through the noise and make it all make sense.

The clashing patterns, the slouchy trousers, the low-key loafs—this is eclectic grandpa style done oh-so-right.

Gucci’s horsebit loafers get all the headlines, but don’t sleep on the house’s other indelible styles—particularly the ’70s-inflected, red-and-green-striped joints modeled here by curator extraordinaire (and occasional GQ contributor) Sargent.

Paul Mescal, a self-described “big advocate for men wearing shorter shorts,” proves here that there’s no better match for said shorts than a killer pair of loafers.