We’re back into action with another handy, super-useful Style Suggestion today on The Style Guide (redundant, but important to note). And unlike recent style suggestions, like what to wear on New Year’s Eve or how to dress for your holiday party, the below outfit is one you can make use of all winter long — particularly when it’s cold and snowy, yet you’ve got a road trip on the horizon. Whether you’re packing up the car for a weekend trip, stepping onto a train for a getaway up or down the coast, or flying cross-country, the focus today is on comfort, style and classic looks. It’s all about ease of layering and pieces that can go just about anywhere — and of course, a handsome, durable weekender bag with which to carry everything. Are you ready to pack up and hit the road? If you need more travel style tips, check out what I packed and wore on a winter trip to Baltimore or a fall trip to Providence — most importantly, visit yours truly on Instagram for a daily behind-the-scenes look at my (overstuffed) closet. Shop away!
The Weekender Bag: Nisolo Leon Weekender in Chestnut — $339.98
When packing for a road trip, it should all start with your bag — right? And there might not be a better place to get a stylish weekender bag than our friends at Huckberry. In particular, the Nisolo Leon Weekender is just the beautiful, handmade leather bag your closet’s been missing. Named for the Mexican city where’s it produced, the Leon Weekender features vegetable-tanned leather and small details like leather zipper pulls and a tan cotton canvas lining for durability. The Leon Weekender is a bit smaller in size than the Owen & Fred Voyager Waxed Weekender, but no less worthy of a purchase.
The Dopp Kit: Nisolo Durango Dopp Kit — $88
You didn’t think we’d get packing for your next trip without considering a stylish men’s dopp kit, did you? And when it comes to complementing the exceedingly handsome Nisolo Leon Weekender, there’s perhaps no better dopp kit to buy than the Durango Dopp Kit. Made with vegetable-tanned leather and featuring what the brand says is a deep design for carrying all of your winter grooming essentials , it’ll look — and age — as great as it performs.
The Jacket: Taylor Stitch Maritime Submariner Jacket — $248
As seen recently on this site’s Style Pick of the Week series, the handsome, vintage-inspired and functional Maritime Submariner Jacket is just what you need to tackle winter travel. Even if you’re only dashing from your car to the airport, you want to be bundled up — that goes for departing and returning in equal measure. And if you’re heading to a cold locale and need to pack light, the Maritime Submariner Jacket — with its custom anchor buttons, beastly boiled wool exterior and slim, casual-yet-rugged fit, is the perfect travel jacket.
The Shirt: Mack Weldon Pima Long-Sleeve Crew — $38
Available in a diverse and essential array of colors, the Mack Weldon team definitely knows what it’s doing in terms of essential, well-made basics. From its Merino Long-Sleeve Tees to its comfortable, slim-fitting and crisp Pima Long-Sleeve Crew Tees, the brand gets it right — particularly when you consider the fact that this is the sort of long-sleeve tee you can wear under a blazer with ease. And if you feel it’s not sharp enough, you can always pack it away and reach for a classic chambray shirt for travel instead. You with me still? Good.
The Denim: Mugsy Jeans Hamms Jeans — $98
Mugsy Jeans is building its brand on providing slim-fitting, comfortable jeans for men that, well, have a little more crotch space (don’t worry, that’s an Esquire.com link). Aside from that dubious distinction, they’re exceedingly easy to wear and move around in, as I found out on an upstate trip to Hudson last fall. And so, they’re a wise pick if you’re going to be sitting down and then moving through a crowded airport all day — but in a classic dark wash, you can wear them right out to drinks once you arrive at your destination.
The Boots: Thursday Boots Brown Duke Boot — $199
Thursday Boots is a favorite of this blog — sometimes weekly — for the way they combine price, quality and versatility (although if you visit here frequently, maybe you’ve picked up a pair for yourself). Slick Chelsea boots are quickly moving from a trend into a versatile, everyday style essential for the modern man — check out how our man David Beckham wears them, for one. And the Brown Duke Boot is crisp, easy to slip on and off going through security, and works with everything from denim and the Maritime Submariner Jacket to a sharp suit on a business trip.
The Socks: American Trench Random Plait Sock in Fire — $10.98
Simple, nice and hole-free socks are a must when traveling — don’t take that for granted. And a crisp pair of American Trench socks really is the pair you need to pick up — heck, if you’re only traveling for a three or four-day weekend, you could feasibly pack only socks from American Trench. The red color and subtle texture here breaks up the blue denim, blue shirt and grey jacket nicely, too. Plus, the sub-$11 price tag can’t be topped.
The Belt: Arcade Belt Co. Crawford Belt in Olive Green — $27.98
Be it sitting in a cramped car, plane or train, comfort is key — witness those stretch jeans near the top of the page. It only makes sense, then, to reach for a belt with just as much stretch, comfort and crisp style The Arcade Belt Co. Crawford Belt is the piece you need for winter travel — it’s easy to slip on and off, it stretches & moves with you, and it nicely complements the crisp blue jeans. Granted, it’s a bit different in terms of color than the brown Chelsea boots shown here, but I’d wager you’ll be more put-together than folks wearing sweatpants — ehh?
The Watch: Luminox Atacama Day/Date Field Watch — $319.98
Take it from a guy who loves an essential casual watch — you need to travel with at least one (or two … or three?). If you need to pack light but still want to travel in style with a timepiece that can do just about anything, something sharp and rugged-yet-refined is the way to go. Enter the Luminox Atacama Day/Date Field Watch. We’re talking PVD-plated stainless steel hardware, a handsome black-and-tan combination, and a tough 45mm case diameter. It might be a bit big on some wrists, but with the rest of this casual ensemble, it should do just fine.
That wraps up the latest style suggestion — did you find it helpful? As with many different style scenarios — from dressing for a weekend coffee date to dressing for a business casual office, many of the same principles apply. That is, fit and comfort — especially comfort — are paramount when hitting the road. And classic pieces, like a well-made Mack Weldon crewneck and dark stretch denim, are excellent places to start. When you consider the versatility and durability of your outerwear and accessories, the Maritime Submariner Jacket and the sturdy, tough Luminox Atacama Day/Date Field Watch are prime pieces to grab. Of course, a remarkably stylish and well-made weekender bag — that’d be the Nisolo Leon Weekender is going to get you from point A to point B (and maybe point C) in style. Ready to travel? Get to it!
Good luck and stay stylish,
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