1 / 6- Free shippingShips in 2 business days
- 30-day returnsHassle-free returns
- Lifetime warrantyMaterials and workmanship
Trail Boss Full-Grain Leather Messenger Bag for 16-Inch Laptops
- Fits laptops up to 16″
- Full-grain leather
- Hidden quick-release latches
- Hidden trolley strap
Built for the daily carry
The Trail Boss messenger is a full-grain leather bag that fits laptops up to 16 inches. An 11″ front pocket with hidden quick-release closures keeps everyday items close without breaking the clean leather front.
Natural grain and slight color variation are part of the look, and the brandy leather gains character with regular use.
Size & specs


- Main compartmentPadded laptop sleeve, phone pocket, slip pockets and an inside zip pocket.
- Front pocket11″ wide, with hidden quick-release closures.
- Rear zip pocketHides a trolley strap that slides over rolling luggage handles.
| Outside size | 15.5″ W × 11″ H × 5″ D |
|---|---|
| Material | Full-grain leather, Brandy finish |
| Interior | Lined |
| Carry | Leather top handle + removable shoulder strap |
| Model | 1910 |

Make it yours
A heated solid brass die is hand-pressed into the leather for a deep mark that ages with the bag. No lasers, no burning.
- Tick Add FireMark™ personalization (+$15).
- Type up to 16 capital letters, A–Z. No numbers, punctuation or special characters.
- We press it by hand.
Reviews
Questions
Will my 16-inch laptop fit?
Yes. Laptop sizes are screen sizes, measured diagonally across the screen, not the width of the laptop. Most 16-inch laptops are narrower than the bag, which is 15.5 inches wide, so they slide into the padded compartment with room to spare. Very thick gaming laptops may not fit.
What leather is it made from?
Premium full-grain leather in a Brandy finish. Full-grain keeps the hide’s natural surface, so every bag has its own markings and develops a patina with use.
How does FireMark™ personalization work?
A solid brass die is heated and hand-pressed into the leather for a deep, permanent mark. No lasers and no burning. Up to 16 capital letters, A to Z. It adds $15.
Can I return a personalized bag?
No. Personalized items are made to order and are final sale. Unpersonalized bags can be returned within 30 days of delivery, unused and in their original packaging.
When will it ship?
Ships in 2 business days. Standard shipping is free.
What does the lifetime warranty cover?
Defects in materials and workmanship under normal use, for the life of the bag.
Do you offer bulk or corporate pricing?
Yes. Buy 2+ items to save 5%, 5+ to save 10% and 10+ to save 15%, applied automatically at checkout. For custom branding, contact Bespoke Leatherworks.
How do I care for the leather?
Wipe with a dry cloth, condition it when it looks dry, let it air-dry if it gets wet, and store it stuffed in a dust bag out of direct sun.