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

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