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

The Friday Read: Maggie Rogers, The Best White Sneakers for Spring and The Best Men’s Work Boots

Thanks for joining us again for another Friday Read here at The Style Guide. It’s pretty wild to be closing out the last week of March and moving into April. The past month was certainly a busy, busy one, what with my Florida spring break trip and my latest #menswear road trip to Pittsburgh to see Local Natives, among plenty of Brooklyn style adventures.  If you’ve been on the road, or find yourself prepping for a spring break trip of your own, shop my suggestion on how to dress for spring break this year. For now though, we’ve got plenty of other seasonal style essentials to cover. For one, did you pick up a stylish spring jacket yet? A recent shopping post on this site covers pieces that are functional and great-looking (of course). And if you need tips on what to look for when buying a leather jacket, there’s an #OOTD entry I think you’ll find helpful and highly stylish.
Sutro Footwear

Elsewhere in style (and trip) planning matters, it was with tons of excitement that I picked up tickets this past week to see none other than The Killers at the excellent Radio 104.5 Birthday Celebration in June! Of course, that show will follow on the heels of Governors Ball here in New York City — are you heading to any spring or summer music festivals? Let me know on Twitter — and shop my picks for how to dress for a music festival in the meantime. And that reminds me … we’ve got a nice mix of music and men’s style in the below reading picks. So, read on, enjoy the weekend and keep up with my real-time men’s style updates via Instagram.
Beckett Simonon

SeaVees

My spring style pick — and available for a nice deal this weekend, too. Photo courtesy of SeaVees.

  • Not feeling in the mood for April Fool’s jokes, but feeling in the mood for some menswear? If that’s the case, the fine folks at SeaVees have a deal for you. On Saturday only (that’s April 1st — AKA April Fool’s), you can get 20 percent off all footwear — including the brand’s new Spring 2017 collection — using the code ‘NOFOOL’ … I’m not even kidding here, folks. My personal favorite pick? The SeaVees Legend Regatta, as featured above and as worn by yours truly on my recent Florida spring break trip . They’ll work with slim chinos, they’ll work with light wash denim and they could just be your new favorite spring sneaker!
  • So, we told you we’d have some music included in this post — right? Well, if there’s been one artist I’ve been listening to on repeat these past few weeks, it has to be the mercurially talented Maggie Rogers. The Maryland native seamlessly blends indie folk, jazz and R&B influences, with a touch of dance pop thrown in. It’s music that’s subtle, nuanced, well-written and beautifully sung — you might want to check on Maggie Rogers tour dates if you like what you hear! Tickets are literally selling out quicker than you can say “viral sensation,” so hop to it!

  • Now, back to menswear — I certainly have my own picks when it comes to classic men’s spring sneakers, and Esquire.com is also here with a  helpful rundown on the best white sneakers to buy for spring. Buy ’em now, wear ’em a ton and look forward to warm weather.
  • In other matters of men’s style, spring travel season — AKA spring break — is upon us, as mentioned earlier. Crucially, the Bradley Mountain Utility Bag is the one bag you need to buy and use for your next road trip. Let me know if you’ve picked it up via the comments below!
  • Last but not least … I rounded up 25 (25!) durable men’s work boots for GearMoose, featuring brands from Danner to Wolverine. Before you tackle your next spring project, grab a pair and get to it.

OK, so that’s this week’s Friday Read — have a great weekend and check back here tomorrow for a spring-friendly Style Pick of the Week.

Enjoy!

-Beau

Greats

Style Pick of the Week: Bradley Mountain Utility Bag

Plenty of exterior pockets, tough specs and handsome looks — your new favorite spring travel bag.

If you can believe it, it’s Saturday again — and that means it’s time for another Style Pick of the Week, this one featuring the essential, adventure-ready Bradley Mountain Utility Bag. If you haven’t yet had the chance to travel in style this month — either due to colder-than-expected March weather or a busy season at work (shoutout to all the accountants out there), hopefully this week’s #menswear pick will inspire you to hit the road soon. The Bradley Mountain Utility Bag is an unexpected, unique piece in terms of its design — part oversized tote bag, part durable weekender. That means you can sling it over your shoulder or carry it by your side — seriously, nothing tops a stylish travel bag. And there’s no question we could all use one of those in our rotation. For quick overnight trips or multi-day stays — such as my own February trip to New Haven — there’s nothing I need more than a handsome, tough piece to carry all my favorite gear; if you’re in the same boat, stick with me here. For starters, know that this bag will work if you’ve got a spring break trip upcoming, or just a much-needed weekend getaway. Crucially, you needn’t worry about having enough room to hold each and every piece of your everyday carry — with seven external pockets, the Bradley Mountain Utility Bag might actually boast the most exterior storage of any bag you own. And the rest of the specs? Well, they’re enough to make you want to buy the Bradley Mountain Utility Bag on the spot — maybe.
Beckett Simonon

Let’s start with the rugged exterior — yes indeed, the 15oz. Martexin waxed duck canvas exterior on the Bradley Mountain Utility Bag is built to withstand everything, from being tossed around a campsite to being tossed into an overheard bin. Even the custom leather straps and detailing should prove sturdy, made from 9oz. oiled and waxed custom leather. Both those design touches mean the entire bag, from top to bottom, is going to get better the more you use it. Whether you’re dressed in casual, classic everyday spring style for a weekend trip or wearing your new favorite long-sleeve polo on a business trip, the Bradley Mountain Utility Bag is going to move with you in style. Of course, this bag certainly leans more rugged — so if you find yourself needing more refined travel luggage for cross-country jaunts, you might want to pass on picking this one up. With that being said, the Bradley Mountain Utility Bag is so well-made and tough that it just might be an essential, much-needed addition to your everyday carry.  What do you think? And where will your own spring travels take you? Let me know via the comments and join us via The Style Guide Facebook page for more great #menswear.

Buy the Bradley Mountain Utility Bag now via Huckberry.  

Greats