Online Shopping Picks: The Best Men’s Weekender Bags for a Road Trip

That bag you’re packing up for your next getaway — is it one of the best men’s weekender bags for a road trip? No? You’re not sure? Don’t worry — it’s taken care of. A stylish weekender bag is the lofty subject we’ll tackle in today’s latest Online Shopping Picks entry — and I think you’re going to like the results.  As we so often talk about here on The Style Guide, developing great style really is the sum of a lot of moving parts. From the stylish  sneakers on your feet to that slim short-sleeve shirt hanging in your closet, looking and feeling great comes down to the details — and that’s certainly the case when it comes to the bag you’re bringing with you on your next road trip.
Florsheim
If the goal is to get out of town in style, you’re going to want a functional, durable weekender bag that looks just as great as it performs. We’re talking about a tough weekender bag that can go from the trunk of your car to the overhead bin to the floor of your rustic, refined boutique hotel without missing a beat. The right bag has got good looks, easy utility and investment-level quality in spades. And as to the below options? Well, I’d say that each of them certainly pass muster. Chime in on Twitter with any thoughts on this list of the best men’s weekender bags, and follow me on Instagram to see how I’m packing in style this summer.

#1. Nisolo Leon Weekender — $397.98

Relatively rare all-leather construction, excellent looks and an agreeable price.

Is the Nisolo Leon Weekender pricey? Yes. Is it a Style Guide favorite for its combination of rugged good looks and smart craftsmanship? That’s also a definitive “Yes.” An all-leather weekender like the Leon Weekender is a pretty rare find these days, particularly with a price tag that’s not too outrageous. Think of this as a stylish weekender bag that’ll look just as handsome with a tailored suit on a business trip as it will with a chambray shirt and chinos on a casual weekend getaway.

#2. Billykirk Large Sport Carryall — $251.98

Billykirk

The rugged ability to serve as both a gym bag and a weekender bag — you should expect nothing less from Billykirk.

Leave it to Billykirk to make a weekender/gym bag that works twice as hard as you’d expect. In one instance, the Large Sport Carryall is a uniquely stylish way to lug your favorite gym gear to and from a morning workout. And the next day, it could reliably serve as a durable weekender bag for an upstate trip. With its use of Cordura material and Mil-Spec hardware — not to mention sturdy, USA-made construction — picking up the Large Sport Carryall is almost like getting two bags for the price of one.

Timex

#3. Bespoke Post Weekender Box — $45

$45 for the Bespoke Post Weekender Box? Too good to be true, right? Wrong.

That price above isn’t a typo. You really can get the Bespoke Post Weekender Box for just $45 (when you sign up for Bespoke Post, that is). In all seriousness, why on Earth wouldn’t you want to sign up for Bespoke Post when the result is a bag like the weekender shown here? Available in a range of colors and made from what the brand calls “thick and capable canvas,” it’s the type of bag that’ll only get better with age — and I’m sure you’ll reach for it time and again. Yes indeed, the Bespoke Post Weekender Box might be the smartest purchase you’ll make this summer.

Nautica

#4. Topo Designs Mountain Duffel — $229

The Topo Designs Mountain Duffel is all business — sleek, no-nonsense and definitely very functional.

If you consider yourself a guy who favors more minimal, functional style and performance rather than bright, loud colors when shopping for a stylish weekender bag, the Topo Designs Mountain Duffel is the bag for you. It’s water-resistant right down to the YKK zippers, and it offers handy design touches like a padded base and side panels (all the better to keep your gear safe). In a sleek black color, it’s a low-key way to upgrade your weekender bag — it’s more than ready for camping trips, hikes or day trips.

#5. Filson Small Duffel — $297

Filson

A richly crafted, durable and timeless bag from Filson — that’s all you can ask for, really.

Leave it to the lauded gear makers at Filson to continually deliver on classic pieces that stand the test of time. While not quite as large in size as some of the other options on this list, the Filson Small Duffel is every bit as deserving of a spot here. It starts with the brand’s attention to detail and namely, Filson‘s own rugged, functional, abrasion-resistant twill. Other helpful design touches — such as the tough bridle leather straps and solid brass zipper — help make this bag an investment-worthy classic.
Ben Sherman

Honorable Mention: Bradley Mountain Utility Bag — $159

A carryall that can also serve as a weekender bag — that’s the way it’s done, folks.

There are simply far too many options out there in terms of stylish weekender bags to end this list at just five. It was a tough call, but the Bradley Mountain Utility Bag just barely missed the cut here (Editor’s note: Catch a full write-up on this bag in our Style Pick of the Week series). Able to be fashioned into a carryall for just about anything you can think of — including your favorite summer gear — the Utility Bag is also the type of bag that could reliably haul enough clothes for a weekend away.  The Bradley Mountain Utility Bag features rugged good looks and the sort of durability that you only get from using a custom oiled and waxed leather construction. That is to say, it’s a one-of-a-kind bag that you need in your summer travel arsenal … now.

END. Clothing

In summary: You need — like, need — at least one of the best men’s weekender bags in your rotation for the months ahead. Whether you reach for a two-in-one bag like the Bradley Mountain Utility Bag or the handsome, durable  Large Sport Carryall from Billykirk is entirely up to you — either one would be a wise move. And a sturdy weekender bag from a heritage brand like  Filson provides both instantly recognizable looks and classic style. If that’s not your cup of tea, you can’t go wrong with a minimally designed number like the Topo Designs Mountain Duffel. And in terms of looks, quality and affordability? Well, the Bespoke Post Weekender Box is a surefire winner, available in a diverse range of colors and geared to go anywhere you can dream up. I’d love to hear your thoughts on the best weekender bags below — and of course, I’m reachable at all hours on The Style Guide Facebook page.

Thanks for reading — and stay stylish!

-Beau

Greats

Style Pick of the Week: Nisolo Leon Weekender

Editor’s note: Expect these posts weekly detailing one standout item coveted by yours truly. Sometimes, these fit within budgetary restrictions and other times, they’re expensive splurges worth saving for. For more Wish List items from Beau, head here, and to see other Style Picks, head here. Portions of this post use affiliate links, off of which a small commission might be earned on purchases.

Your new favorite weekender? Possibly. The only one you'll need to buy again? Likely.

Your new favorite weekender? Possibly. The only one you’ll need to buy again? Likely.

There comes a time in every guy’s life when he looks at his weekender bag and thinks “Y’know, there’s something missing.” Right? Right. Well, we’re here to solve the conundrum between style, functionality and durability this weekend with this Saturday’s Style Pick, the handsome, extremely well-made and essential Nisolo Leon Weekender.  You might recognize this bag from this site’s recent feature on how to dress for winter travel, but we’re taking a bit of a deeper dive today. Now, a weekender bag probably isn’t going to take care of all of your travel luggage needs — especially if you’re on the road for longer than, well, a weekend — but if you need a new bag for quick trips and the like, the Leon Weekender just might be exactly what the doctor ordered. As sold via everyone’s favorite third-party men’s lifestyle site — we’re talking ’bout Huckberry — a stylish weekender bag is every bit as important to pick up as tough winter boots or a stylish pair of winter gloves. And whether you’re gearing up in fall travel style or hitting the road in winter (or really, any other season), you’re gonna want to look good. Trust us on that one. And why is the Nisolo Leon Weekender the one to buy now? Well, it’s got great looks, durability and functionality — and that’s just for starters.
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Perhaps a few travel packing tips worth stealing. Photo courtesy of Huckberry.

Perhaps a few travel packing tips worth stealing. Photo courtesy of Huckberry.

Nisolo tends to fly under the radar a little bit as far as notoriety goes, but that’s not a bad thing — it just means you’re in on the ground floor. You might recognize them from a recent tailored style #OOTD — yessir, they make beautiful leather chukkas, too. And of course, the brand specializes in handsome, versatile goods with just enough rugged edge — that’s what makes the Leon Weekender so essential.  It’s handmade in Mexico — a country with a rather surprising amount of excellent leather producers and factories — out of vegetable-tanned leather that should develop a beautiful patina over time. The tan cotton canvas lining adds a dash of durability to protect your gear, while leather zipper pulls are a thoughtful design touch. It might just be the perfect weekender bag — it’s dressy enough to look right at home with a business casual travel outfit, yet it’s got enough character to work as an accessory in a more rugged winter style ensemble. Size-wise, it’s a bit smaller than the relatively roomy Owen and Fred Voyager Waxed Weekender, so there should be no issues packing it up with travel style essentials. An added bonus? You can pick up something like the equally handsome Nisolo Durango Dopp Kit for a full set of reliable, durable travel gear from the same brand.  And although the price tag is a tad high, it’s the type of investment you won’t regret making — this is a bag you’ll absolutely have for years to come; just think of the stories and adventures you’ll have. On that note philosophical note, we’re wrapping up this week’s Style Pick. We’ll see you on Monday as we get back to the grind.

Thanks for reading,

-Beau

Get the Nisolo Leon Weekender now via Huckberry.

Style Suggestion: How To Dress for Winter Travel

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

A supremely stylish and tough leather weekender bag.

A supremely stylish and tough leather weekender bag.

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

The ideal way to complement your new favorite weekender bag -- right?

The ideal way to complement your new favorite weekender bag — right?

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

Welted handwarmer pockets and patch flap pockets translate to functionality, top-notch construction and great style.

Potentially your new favorite travel jacket for cold weather — trust me.

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

A surprisingly crisp long-sleeve tee comfortable for travel and layering.

A surprisingly crisp long-sleeve tee comfortable for travel and layering.

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

Dark, slim-fitting jeans with a ton of comfort and stretch -- as good as it gets.

Dark, slim-fitting jeans with a ton of comfort and stretch — as good as it gets.

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

Crisp, sharp and versatile for travel and beyond.

Crisp, sharp and versatile for travel and beyond.

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.

Beckett Simonon

The Socks: American Trench Random Plait Sock in Fire — $10.98

Subtle texture, major style points and a great price.

Subtle texture, major style points and a great price.

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

A belt that combines casual style with stretch & comfort.

A belt that combines casual style with stretch & comfort.

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

A rugged-yet-refined timepiece for travel and activities once you get to your destination.

A rugged-yet-refined timepiece for travel and activities once you get to your destination.

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.
Frank & Oak

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,

-Beau