world of men's style / fashion / grooming

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The Dilemma of the Roller Bag

This note recently arrived in the Kempt inbox, timed for a February getaway:

I am looking for a leather or canvas traveling roller bag. Enough to fit a decent wardrobe. My J&M is falling apart and I wanted something with style. Any suggestions?

It’s a simple question, but a tough one. We prefer to stay far away from roller bags—just as we prefer to travel by convertible, bullet train or hydrofoil—but life is not always as we’d like it to be. Sometimes you need to leave your weekender bag at home in favor of something that fits in an overhead compartment and doesn’t strain your shoulder.

Handsomeness usually comes in a distant third, but it doesn’t have to. At least, not if you’re buying the right bag...

The golden numbers here are 22" x 14" x 9". That’s the size of a typical carry-on space, and any bag that’s larger than that is going to bring you untold suffering. Given the headaches involved, it’s surprising how many bags come in just a little bit bigger than the space they’re meant for (this otherwise-handsome Ghurka bag, for instance), so it’s important to stay vigilant on that point.

After that, your job is standing apart from the crowd of black tactical cloth and hard-shell plastic, which means you’ve got quite a few options. The most handsome of the bunch is this Floto model, provided you can stand to turn over that much Italian leather to the baggage handlers of the world. If not, Filson makes a pretty good rollaway in the same style as their ubiquitous briefcase, which should only improve with a few well-placed scuffs.

If it still looks a bit too boxy for you, we recommend bicep curls and packing light.