Online Shopping Picks: The Best Men’s Weekender Bags

Editor’s note: For even more online shopping picks covering everything from watches to spring and summer style, head here.

As spring rolls into summer, there’s a very good chance that a lot of us are going to be hitting the road for vacation quite a bit more than during the doldrums of winter. This is definitely the case for yours truly, as I just trekked down to Washington, D.C. for the weekend earlier this month, and have a few more trips in the works. While longer travels certainly require larger luggage, traveling for just a handful of days presents some style conundrums — both in matter of what to pack, and what to pack that gear in. A stylish weekender bag is going to be your best friend in these situations — most have just enough room to hold multiple pairs of shoes and multiple outfits, plus any other gear you might need. And a great-looking bag is the ideal compliment to a sharp travel outfit. Plus, making that upgrade from a standard gym bag or duffle is yet another step on the path that is constantly trying to improve your personal style. Heck, it’s just fun to have a bag that happens to look as good as what you’re wearing. Make packing and traveling easy with one of this site’s picks below for the best men’s weekender bags, and get to booking that flight. Let me know what you think on The Style Guide Facebook page, too!

#1. Owen & Fred Voyager Waxed Weekender — $275

A bag that's built for wear-and-tear, yet still manages to look mighty handsome.
A bag that’s built for wear-and-tear, yet still manages to look mighty handsome.

The first entry on this list is a real tried-and-true, trip-tested bag that’s made in America and built with a ton of quality. Yes, the Owen & Fred Voyager Waxed Weekender  is certainly a stunner, made from Martexin Original Waxed canvas (some of the best of the best) and finished off with durable leather straps from Wickett & Craig, one of the oldest tanneries in the country. It’s beastly, stylish and built to break in over time, complete with two interior zippered pockets for extra storage. After taking it with me on my trip to Washington, D.C., I can say you’ll be very pleased with it indeed.

#2. Everlane Dipped Weekender — $115

An affordable alternative to more expensive options, with just as much style.
An affordable alternative to more expensive options, with just as much style.

Whereas the above Owen & Fred bag packs a  heck of a punch in both quality and price, the Everlane Dipped Weekender is a more affordable answer to the question of what you should travel with this summer. It’s made from twill and features a neat, screen-printed look that contrasts nicely with the black leather straps. Everlane has a brand really does it all now from its Slim Pant to bags like these, which really put them on the map. While the price might seem at odds with the expected quality, it’s part of Everlane’s commitment to transparency, and that should work out nicely should you buy this bag.

#3. J. Crew Harwick Weekender Bag — $148

A more casual alternative from a brand that does a lot of things well.
A more casual alternative from a brand that does a lot of things well.

Just as Everlane has expanded its product categories over the years, J. Crew has continued to stick with making all sorts of stylish accessories for guys — like the Harwick Weekender Bag. It’s nylon, so it’s decidedly more casual in construction and looks than the Everlane or Owen & Fred options, but the Dark Navy color should stylish and versatile for laidback weekend trips. It packs in a shocking eight pockets — that’s more than tons of bags on the market, and it means all of your gear — from a classic white Oxford to your stylish dopp kit — stays separate (and clean).

#4. Wood & Faulk Grand Tourer Weekend Bag — $175

A stylish-looking offering from an under-the-radar brand.
A stylish-looking offering from an under-the-radar brand.

Have you heard of Wood & Faulk? They’re a new brand for this style writer, but given the stunning looks (and presumably, quality) of their Grand Tourer Weekend Bag, they’re worth watching. This piece is made from tough-looking waxed canvas and features leather accents from S.B. Foot Tanning Co. — the same tannery that produces leather for Red Wing Shoes. Talk about stunning quality packed into one piece. End pockets and an inner zip pocket offer additional space, and the brass hardware finishes off this bag nicely.

#5. Troubadour Fabric + Leather Weekender — $855

A pricey, minimal and super-premium weekender bag.
A pricey, minimal and super-premium weekender bag.

It wouldn’t truly be an Online Shopping Picks entry if we didn’t finish things off with a stylish and yes — incredibly expensive — weekender bag. The Fabric + Leather Weekender  features vegetable-tanned leather and a minimal, premium look thanks  to the black leather and nylon fabric accents (although the Navy, Khaki and Olive colorways look mighty nice, too). It’s an investment bag that certainly would look right at home alongside your best travel suit — if you’re the type who travels a lot for business but wants a bag that’s different than a standard rolling suitcase, this is the bag you need.
Frank & Oak
While each of the above bags are suited for different kinds of situations — particularly the Troubadour weekender — each is going to stylish and durably complement your travel ensemble and any stylish travel accessories you might be bringing with you. Maximizing a great price, tough quality and handsome looks is going to be critical, too — and hopefully, do-able with any of the above picks. If you’re still searching for that perfect bag, an option from the likes of Herschel Supply Co. might work well. But in the meantime, let me know on Twitter if I missed any picks or key brands!

Stay stylish and safe travels,

-Beau

Florsheim

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