Fashion & Style

What to Wear: The Best Men’s Outfit for a Winter Weekend Getaway

If the phrase “rugged winter weekend” conjures up images of freshly fallen snow, a roaring lodge or cabin fireplace, a rich stout in hand, and your favorite winter gear, well … that’s exactly what it should conjure up. We’re talking about the type of winter weekend (and the sort of accompanying gear) that involves going off the beaten path and exploring a new locale, preferably with tough winter layers in tow. Be it a cabin getaway or a retreat to that upstate haven you’ve read so much about, these gear picks are primed for 48 hours (or more) of stylish adventure.

Flint and Tinder Waxed Trucker Jacket

Flint and Tinder Waxed Trucker Jacket

There might not be a casual-yet-tough winter jacket we recommend more than the Flint and Tinder Waxed Trucker Jacket (lined with flannel for added warmth). Available in a range of colors and crafted from a custom waxed fabric, it’s tough enough to stand up to the elements and stylish enough to wear to grab a beer after your work is done.

Outerknown Blanket Shirt

Outerknown Blanket Shirt

What’s not to love about the Outerknown Blanket Shirt? It comes in a truly huge array of stylish plaids and rich colors (including the option shown above), it’s crafted from rugged-yet-mobile heavyweight organic cotton twill, and it layers up stylishly with your waxed trucker jacket.

Taylor Stitch Heavy Bag Henley

Taylor Stitch Heavy Bag Henley

For when winter weather simply won’t quit, reach for the tough Taylor Stitch Heavy Bag Henley, made from upcycled materials and crafted to be as versatile as you can dream up (it works especially well under a cotton twill shirt).

Bluffworks Departure Slim Travel Jeans

Bluffworks Departure Slim Travel Jeans

Slim black jeans that just so happen to be comfortable and ready for travel? It sounds too good to be true, but that’s what you’re getting with Bluffworks. These jeans are packed with hidden pockets for your everyday carry and feature an edgy-but-versatile black wash for a full weekend of wear.

Blundstone Original 550 Boots

Blundstone Original 550 Boots

For maximum traction and toughness in nasty winter weather, plus the ease of slipping them on and off with thick boots socks, it’s hard to go wrong with Blundstone’s classic boots.

Armitron Brown Leather Watch

Armitron Brown Leather Watch

For a winter weekend getaway, sometimes, an affordable leather watch is your best bet. It’s put-together enough to wear during a day of travel, yet it’s stylish enough to hold its own as you head out for an evening beer.

WP Standard Canvas Weekender Bag

WP Standard Canvas Weekender Bag

If your upstate cabin is calling, or if you simply want to get out of town to that rustic boutique lodge you’ve read about — or if you’ve got more adventure-filled pursuits in mind “off the grid” — then you’re going to need a tough weekender bag to get there. WP Standard has you covered.

Editors' Recommendations