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Trail Boss Leather Messenger Bag with Carry Handle

Trail Boss Leather Messenger Bag with Carry Handle

Regular price $198.00
Regular price $300.00 $300.00 Sale price $198.00 (34% OFF) Save $102.00
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Color: Brandy
Model Number: 1910
Feature Highlights
  • Material: Premium Full-Grain Leather in Brandy
  • Laptop Capacity: Fits laptops up to 16 inches
  • Dimensions: 15.5" W × 11" H × 5" D
  • Front Storage: 11" pocket with hidden quick-release closures under leather latches
  • Travel Ready: Rear zipper pocket with hidden trolley strap for luggage handle
  • Interior Organization: Padded laptop sleeve, phone pocket, slip pockets, and zipper pocket
  • Carry Options: Reinforced leather top handles and removable shoulder strap
  • Style: Rugged Western-inspired professional briefcase
  • Customization: FireMark™ personalization available

Built for daily work, meetings, and travel, the Trail Boss keeps your laptop and essentials organized in a full-grain leather messenger bag with both top-handle and shoulder carry. A padded laptop sleeve, quick-access front pocket, and hidden trolley strap help you move from your commute to the airport without changing bags.

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The Trail Boss is a full-grain leather messenger bag made for professionals who carry their work with them. Its 15.5" W × 11" H × 5" D profile provides room for a laptop, documents, chargers, and everyday essentials while keeping your carry organized and easy to access.

An 11-inch front pocket with concealed quick-release closures keeps frequently used items close at hand without interrupting the bag’s clean leather exterior. Inside, a padded laptop sleeve fits laptops up to 16 inches, while a phone pocket, slip pockets, and interior zipper pocket help separate smaller essentials.

For business trips and airport days, the rear zipper pocket conceals a trolley strap that slides securely over the handle of rolling luggage. Carry it by the leather top handle or use the removable shoulder strap when you need hands-free comfort.

Finished in Brandy full-grain leather, the Trail Boss is designed to gain character with regular use. Natural grain, slight tonal variation, and a developing patina are part of what make each bag distinct.

Material: Premium Full-Grain Leather in Brandy

This leather messenger bag is designed for everyday professional organization and travel convenience. The spacious interior accommodates laptops up to 16 inches along with documents and work essentials. A front 11-inch pocket features hidden quick-release closures beneath traditional leather latches, allowing fast access while preserving the rugged aesthetic. The rear zipper pocket includes a hidden trolley strap so the bag can securely slide over rolling luggage during travel. Inside, the briefcase provides organized storage with a padded laptop compartment, two slip pockets including a phone pocket, and a secure zipper pocket for valuables. Durable leather carry handles and a removable shoulder strap allow comfortable carrying throughout the workday.

Made from premium full-grain leather in Brandy, the Trail Boss retains the natural character of the hide. With use, the leather may develop a richer tone and a distinct patina.

Because leather is a natural material, grain patterns, markings, and color variation are normal. To help maintain the bag, avoid prolonged exposure to water, wipe away spills promptly, and use a leather conditioner suitable for full-grain leather when needed.

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    Made for You, with a Story

    The Trail Boss is for people whose work does not stay in one place. It is built to carry the essentials you rely on through commutes, meetings, airport terminals, and long days on the move.

    Its messenger-bag layout keeps work gear organized while the top handle and shoulder strap give you flexible ways to carry it. Over time, the Brandy leather develops its own character—making the bag feel more personal with every mile.

    Born Tuff. Backed by Grit.

    Add a personal touch with FireMark™ customization, our heat-branding process that permanently imprints initials or custom text into the leather. FireMark™ creates a bold and lasting mark that enhances the natural character of the leather while making your briefcase uniquely yours.

    Built from the Real Deal

    Whether you’re breaking trail or breaking in your gear, Wyoming Jack products are made from full-grain leather — the toughest hide out there.

    Each piece is carefully cut, stitched, and finished with precision using:

    • Heirloom-grade leather
    • Solid brass hardware
    • Stitching that holds up for decades

    NO SHORTCUTS. NO PLASTIC. JUST GEAR THAT GETS BETTER WITH EVERY MILE.

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