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The 24 Best Shoes for Every Occasion

Sneakers, trainers, dress shoes and slip-ons.


Shoes are often an outfit’s focal point. Whether or not you want them to be, they’re statements about your aesthetics, personality, disposition and, at times, income. Since you can tell a lot about a person from their shoes, a good pair is your most important accessory — so stock up and lace up (or slip on) the right way.

Canvas Sneakers

This classic style has been the definition of casual footwear for decades.


1970s Chuck Taylor All Star by Converse $85

Grounder by Todd Snyder + PF Flyers $130

Canvas Sneakers by Maison Kitsuné $195

Skagway by Visvim $460


Understated trainers to any laid-back outfit.


Classic Leather SM by Reebok $79

MRL996DP by New Balance $125

Flyknit Racer by Nike $159

Marathon Trail Sneakers by Spalwart $290

Leather Sneakers

The canvas sneaker, refined: these kicks are appropriate in most any setting.


OG Old Skool LX by Vans Vault $99

The Royal Suede Sneakers by Greats $170

Original Achilles Sneakers by Common Projects $410

Suede Sneakers by Feit $520

Dress Shoes

The complement to every pair of casual shoes in your closet.


Dylan Wingtip Brogues by Grenson $380

Chetwynd Brogues by Church’s $745

Chelsea Oxfords by Edward Green $1,220

City II Oxfords by John Lobb $1,340

Slip-On Shoes

Easy on, easy off.


Slip On by Shoes Like Pottery $129

Vass Sneakers by Saturdays NYC $160

Garda Slip On by Diemme $295

Summer Walk Loafers by Loro Piana $750

Casual Shoes

Good for the easy-going office or a weekend around the city.


Wallabee by Clarks $109

Weekender Oxford by Red Wing Heritage $220

Crepe Sole Derby by AMI $359

Drew Suede Derby by Grenson $400

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