If you play your cards right, a bag is the kind of investment you make once and then enjoy for pretty much the rest of your life. I’m not talking about a bag you buy at the last minute because you’ve got a trip coming up and you need something—anything—that’ll just keep your stuff in one place. I’m talking about a bag that’s so smartly designed, so sturdy, and so damn perfect that you look forward to packing it and carrying it around almost as much as you look forward to getting out of town.
Bennett Winch’s weekender is just that kind of bag. It’s the signature style from the British brand, which makes its luggage by hand in England using materials that are as hard-wearing as they are luxurious. And once you take a closer look at all the good ideas and expert craft that have gone into it, you’ll understand exactly why it’s such a standout. Which is exactly why we decided to team up with the company to make the new, collaborative Bennett Winch x Esquire Weekender.
Though it’s been in business since 2014, Bennett Winch first popped up on our radar a couple years ago. We were at Pitti Uomo in Florence, a twice-a-year trade show where brands from around the world get together to show off their latest and greatest. Truth be told, it’s easy for a smaller operation like BW to get lost in the crowd—but it didn’t. The product was just too good. So we wrote about it. And then we sat down, opened up a couple of beers, and started talking about how to make something truly special.
The Weekender is already a feat of modern engineering mixed with the utmost appreciation for classic style. The bag’s exterior is made from a super-heavy-duty, 24-ounce waterproof canvas that’s damn near indestructible. The base is made from tough-as-nails Tuscan leather, as are the handles, which are finished with military-grade cotton webbing (same as the shoulder strap). The interior is filled with modern upgrades like waterproof shoe compartments and a padded laptop sleeve, but the look is timeless—subdued, and guaranteed to feel just as relevant in ten years as it does today.
We decided to put our own spin on that vibe by amping up the sleekness and adding a little Esquire personality into the mix for good measure. The original black version of the Bennett Winch Weekender features brass hardware. That’s great if your tastes lean more traditional; we wanted something with a little more edge. So we switched in matte black zippers, snaps, and D-rings. When everything’s stowed away inside, this thing is as stealthy as they come.
When you open it up, though, it’s a whole other story. The entire lining—from the main compartment to those unbelievably handy shoe compartments—is done in a bold shade of Esquire-approved orange. It’s not the sort of thing most people will see on the street, unless you’re grabbing your sunglasses or passport from the easy-to-access exterior zip pocket. But that’s exactly the point. You don’t need to go completely over the top to broadcast your own good taste, and neither does your bag. Still, a little color in the right places is always a good time.
We finished things off with a small touch to illustrate just how special this bag is: On the base, each piece is individually numbered. There are only 50 bags total in this limited edition collaboration, which just launched today, and you’ll know exactly which one you have. After that, it’s just a matter of throwing in the necessities—the bag is sized at a sweet spot that means it’s not too big for a couple days off, but can easily flex to accommodate an entire week away—and hitting the road.
And once you get out there, don’t be surprised if you catch a few envious eyes glancing towards your luggage.