Casual Shoes

10 Shoes for Every Occasion

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1 / 11

You’ve got your gym shoes, work loafers, and fancy lace-ups, but spending an afternoon standing in line at Lord and Taylor sounds a lot like torture. We’ve got your feet covered for the in-between days where tennis shoes won’t cut it. Our list is to the point—and with prices that won’t kill your bank account.

2 / 11

Best for the Bar

Giorgio Brutini—Leinart loafer

Trekking through any bar on any happy hour or night out, you’re sure to encounter floors covered with a layer of sticky booze, street sludge, and other unnamed substances. You need durable, comfortable, sharp loafers—that you won’t feel bad throwing away should a beer fight erupt on Sunday Funday. Georgio Brutini offers casual, yet bar-friendly, penny loafers at the right price point. ($60; giorgiobrutini.comOpens a New Window.)

3 / 11

Best for a Dinner Party

Fluevog Shoes—Prophesy Breton dress shoe

Proper enough to wear as a dress shoe, these burgundy lace-ups offer a trendier take on stuffy business oxfords. Canadian shoe designer John Fluevog lives by his company’s motto, “Unique soles for unique souls.” Break them out for your next formal get-together—or just to look cool reading the paper in your local coffee shop. ($189; fluevog.comOpens a New Window.)

4 / 11

Best for Casual Wear

Pointer Footwear—Taylor sneaker

Slip-on, casual shoes with a stylish flair should be a staple of every man’s shoe rack, and that’s why Pointer created this hybrid sneaker-boat shoe with a moc stitch and leather laces. Easily throw these on for a comfortable walk just about anywhere. ($119; <a data-cke-saved-href=”http://www.pointerfootwear.com/index.php/footwear/mens/Taylor/Taupe” target=” href=”http://www.pointerfootwear.com/index.php/footwear/mens/Taylor/Taupe” target=” _blank”=””>pointerfootwear.com)

5 / 11

Best for Rain

Tretorn—Stråla Vinter Klar boots

We know—rain boots are tough. There’s a fine line between practicality and losing your masculinity. But there’s no reason to ruin a pair of non-waterproof shoes when the weather’s crap. These short cut boots, designed by Puma’s sister company Tretorn, tuck discretely under pant legs, keeping you dry and looking smart. Try these out, and you’ll be laughing at the dude in chukkas. ($70; tretorn.comOpens a New Window.)

6 / 11

Best for Snow

Timberland—Rime Ridge 6 Inch Waterproof Duck Boot

When the elements get rough, a strong, waterproof boot is key. These bad boys are perfect for snow shoveling, chopping wood, or trekking through ice. And they’re insulated so your feet stay dry and toasty. ($150; timberland.comOpens a New Window.)

7 / 11

Best for Lounging

L.L. Bean—Double-Sole Slippers

Whether sitting by a crackling fire or letting the dog out for his morning pee, every man needs his slippers. Leave it to L.L. Bean to know what a man’s foot wants to wake up to every morning…and come home to every night. These bison leather moccasins come with multiple linings, from cushioned fleece to genuine shearling. ($89; llbean.comOpens a New Window.)

8 / 11

Best for Style

Vans—Military Ludlow

For a casual stroll around town or any time you leave the house, these kicks are a step up from your basic white sneakers. Once reserved to skaters, Vans have added a contemporary flair to their brand with designs like the Military Ludlow. Throw them on for comfort and a preppy-hipster style. ($80; vans.comOpens a New Window.)

9 / 11

Best for Working Outdoors

Red Wing Shoes—202 Men’s 6-Inch Boot A sturdy workboot can be functional, but still worn in day-to-day settings. Made of copper worksmith leather, these Red Wing boots are durable for outdoor and manual labor. Their signature oiled, red-brown color makes them decent to wear as a fashion statement as well. ($199; redwingshoes.comOpens a New Window.)

10 / 11

Best for Warm Weather

Sebago—Wentworth Two Eye boat shoes

The boat shoe is the perfect alternative for the toe-shy guy in warmer months. This nubuck pair from Sebago offers a more unique look, while still providing the slip resistance every docksider should. ($95; sebago.comOpens a New Window.)

11 / 11

Best for Versatility

John Varvatos Hipster Chukka

This suede chukka works for just about any season. Unlike other more casual shoes, they can be dressed up for finer occasions. A pair like these are your go-to for dining out, seeing a show, or any weekend activity—just don’t run around wearing them in the rain. ($118; johnvarvatos.comOpens a New Window.)