A few weeks ago, a friend of mine (and blog reader) asked me about recommendations for great weekender bags. It got me thinking – now that winter is finally thawing out, I’m sure lots of us have our eyes on spring or summer getaways. While hitting the road for a vacation is always fun, a big part of the process is how you’re getting there & what you’re packing. And if you’re kitted out in a stylish get-up for the road, you need a bag that’s equally as sharp. Backpacks and sports duffle bags, although functional, don’t provide nearly enough room or the looks needed for longer travel. And while formal briefcases or suitcases work for business trips, the weekender bag is all about providing enough room for the essentials — and doing so in an easygoing fashion. Here are 5 great bags for the road ahead.
#1. Navali Stowaway Weekender Bag — $159.99

The Navali Stowaway Weekender Bag comes with a lifetime warranty, and should last a good long while.
First seen on this blog back in August of last year, the Carafe color pictured here is now gone – but it’s been replaced with an equally stylish washed navy option or a spring-like “Sand” shade. The blue cotton canvas contrasts nicely with the brown leather fastenings, but it’s not all for show. Exterior pockets with strong buckle fastenings, tough zippers, a thick & comfortable shoulder strap and just enough for the essentials make this bag worth the price. Dimensions are 22″ width, 12″height, 8 1/2″ diameter.
#2. J. Crew Abingdon Weekender Bag — $198
It’s tough to go anywhere on Siblings with Style without finding a J. Crew item in a shopping roundup — this is one company doing many things exceptionally. The Abingdon is slightly bigger than the Navali above in terms of height (17 1/2″), width (26″) and diameter (9 1/4″), so it can certainly carry more goods & take a bit of a beating. The waxed cotton canvas construction should age very nicely with increased usage too.
#3. Everlane Twill Weekender — $95
Everlane delivers a much more minimal, modernist (and cheaper) take on the weekender bag. The brand keeps things simple with a grey cotton twill exterior and black leather fastenings — no aged waxed cotton here, folks. Everlane’s bags really put the brand on the map and continue to be quite popular. Having used an Everlane twill weekender pretty extensively across the past summer in New York, these bags can definitely take quite a lot for the price.
#4. Filson Large Duffel Bag — $358
Filson has something the other brands on this list don’t — real, true heritage when it comes to make hardy outdoor gear. Only in recent years has the brand become known more among the fashion community, but it’s got years of experience outfitting hunters, fishers and outdoorsmen. Its bags are crafted from the same durable mindset. This duffle is a true beast of a bag, guaranteed for life and by far the most substantial weekender listed. The olive & tan versions are backordered, but navy and brown are in stock.
#5. Shinola Signature Duffle — $1,250
So this post isn’t really advocating you go out and drop more than A GRAND on a single bag. But, it’s always worth it to scout out what options are out there – and maybe keep a goal in mind for a future investment. This particular bag looks beautiful and features outstanding Horween leather and is individually stamped and numbered — those are the kind of details that bring the price up. The hardware is solid brass, and despite being leather, this bag should not only hold up but also age exceptionally well (it better for that price!). Available in black & brown, with a cognac number coming soon.
NOTE: Other bags that just missed the cut here include J. Crew Factory’s somewhat smaller but very affordable Carson duffle bag, Navali’s Waxed Stowaway Weekender in Olive and Frank & Oak’s Genuine Italian Leather Weekender. JackThreads is also stocking quite a few weekender bags for low prices at the moment.
What’s your favorite from this list? Any idea what you’ll be buying for your travels?





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