Photo by John Lawton

1. No. 1 Grip Bag

Handmade by a purveyor of fine leather goods in Lynnville, Tennessee, this bag was patterned after those used for train travel at the turn of the last century. The bottom even features clever straps to stash a standard umbrella. $675; colonellittleton.com

2. Bannack Bag

This bag is equal parts Old West cowboy and present-day city slicker since it’s hand stitched in Montana from saddle leather and miraculously keeps clothes from getting wrinkled, thanks to a genius partition right down the middle. $990; bozemanwatchco.com

3. Explorer Bag

An heirloom-worthy choice made by Tusting, a family-owned company in England that’s been crafting some of the world’s most beautiful leather bags for 130 years. $699; magnums.net

4. No. 166 Overnight Bag

“We really appreciate the old American work-wear aesthetic,” says Billykirk designer Chris Bray of the No. 166 bag he designed alongside brother Kirk Bray. The bag borrows its shape from tool bags used by tradesmen for over a century. $345; billykirk.com

5. Sierra Duffel

Long before the advent of nylon gear, this is the kind of bag that one would have taken on the trail or on safari. Nowadays, the classic leather and canvas construction feels just right for a weekend away. $148; fossil.com