Bigger. Bolder. Built for the long haul.

The Roosevelt Leather Pilot Bag – XL takes everything you love about the original and scales it for greater adventures. Inspired by Theodore Roosevelt — a man who carried the weight of a nation and still found time to disappear into the wild — this larger version is designed to handle more: more gear, more miles, more stories.

Crafted from the same rugged water buffalo hide, the XL offers additional space without sacrificing the timeless utility of the original. Four buckled exterior pockets keep essentials at the ready — whether it's maps, chargers, notebooks, or gear you need in the moment. Inside, the spacious main compartment easily fits a 17” laptop, with room to spare for clothes, books, or a weekend’s worth of travel. Zippered exterior pocket for quick access, and interior pockets adds order to the chaos.

Whether it’s overhead on a flight or tossed in the back of a truck, the Roosevelt XL is your companion for the journeys that demand more.

To keep your bag ready for the road ahead, clean and condition the leather every few months to prevent cracking or buildup. This one’s made to go the distance.