SALEWyoming Jack Trail Boss leather messenger bag with carry handle, front view showcasing sturdy design and premium leather material.1 / 6
  • Free shippingShips in 2 business days
  • 30-day returnsHassle-free returns
  • Lifetime warrantyMaterials and workmanship
Trail Boss Collection ›

Trail Boss Full-Grain Leather Messenger Bag for 16-Inch Laptops

$198.00$300.00SAVE 34%
Color: Brandy· Model 1910
  • Fits laptops up to 16″
  • Full-grain leather
  • Hidden quick-release latches
  • Hidden trolley strap
5%2+10%5+15%10+
1
Or 4 interest-free payments of $49.50 with Shop Pay
Complete the set
Total for

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.

Full-grain leatherBrandy finish
Padded laptop sleeveFits laptops up to 16″
11″ front pocketQuick-release closures under leather latches
Travel readyRear pocket with hidden trolley strap
Wyoming Jack Trail Boss leather messenger bag with carry handle, featuring a rugged design and adjustable shoulder strap.

Size & specs

FRONT
Trail Boss Leather Messenger Bag with Carry Handle, front view with width and height
W 15.5″ × H 11″
SIDE
Trail Boss Leather Messenger Bag with Carry Handle, side view with depth
D 5″
HOW LAPTOP SIZE IS MEASURED
16″ screen laptop ≈ 14″ wide screen size is measured corner to corner → 16″ laptopfits with room to spare bag 15.5″ wide
What fits inside
Laptop up to 16″ screenDocumentsCharger and cablesPhonePens and cards
Inside: separate zippered compartmentsEvery section closes on its own
  1. Main compartmentPadded laptop sleeve, phone pocket, slip pockets and an inside zip pocket.
  2. Front pocket11″ wide, with hidden quick-release closures.
  3. Rear zip pocketHides a trolley strap that slides over rolling luggage handles.
Outside size15.5″ W × 11″ H × 5″ D
MaterialFull-grain leather, Brandy finish
InteriorLined
CarryLeather top handle + removable shoulder strap
Model1910
Trail Boss Leather Messenger Bag with Carry Handle, ready for FireMark personalization
FireMark™ personalization

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.

  1. Tick Add FireMark™ personalization (+$15).
  2. Type up to 16 capital letters, A–Z. No numbers, punctuation or special characters.
  3. We press it by hand.
Personalized items are made for you and are final sale.

Reviews

Customer Reviews

Be the first to write a review
0%
(0)
0%
(0)
0%
(0)
0%
(0)
0%
(0)

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.