Trail Boss Hat | Black

Regular price $45.00

In stock, ships within 24–48 hours
Description

This one knows exactly where it's from, address stitched right on the side panel.

Unstructured front panel, so it breaks in instead of holding a shape. Snapback closure, one size fits most. Built to sit low and get worn every day, not saved for good.

Details

  • Gold Ski Bum Cowboy 2026 patch
  • Unstructured front panel
  • Classic snapback closure
  • Side panel embroidery: 10 E Broadway Ave, Jackson, WY 83001
  • Designed in the Tetons
Shipping

Hats and accessories ship within 24–48 hours.

Garments are offered in limited runs. Some ship right away, while others are made to order and typically ship within 2–3 weeks, depending on availability.

We produce intentionally to reduce waste.

Ski Bum Cowboy is not responsible for packages lost or delayed by the carrier.

Returns/Exchanges

We accept returns or exchanges for store credit within 7 days of delivery.

If you receive the wrong item or your order arrives damaged, contact us right away and we’ll make it right.

Free Brand Pack with Every Order

Free Brand Pack with Every Order

Includes an enamel pin, matchbook, and stickers.

$18FREE

  • 5 stars: 23 (100%)
  • 4 stars: 0 (0%)
  • 3 stars: 0 (0%)
  • 2 stars: 0 (0%)
  • 1 star: 0 (0%)
Some of the reviews shown are from related products the merchant grouped with this one.
J
Jacqueline Beley

Fits amazing. Perfect partner for weekend adventures

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Ike

Like to have a hat that goes with everything I wear, this is it. It’s basic enough to go with any outfit but the attention to detail with the patch and stitching is money. The fit of these hats is exactly what I look for. Shipping was fast as well, will definitely be back for many more.

I
Ike

This color is so sick. Red is the color I reach for a lot in my closet so this hat pairs perfectly. Fit is excellent!

I
Ike

This is my go to hat for everything. I wear it everyday, I’ve never found a hat that I like more. The fit is perfect, color is beautiful, and details are flawless. Will definitely be ordering more of these.

C
Chelsea

Love this hat and all the swag that came with it. I’ve already put it together with multiple outfits and it’s the star of the whole fit.

H
Hunter Jones

I’m so happy with my order! The hat is such good quality. There are so many tiny details that you can tell a lot of thought were put into. I’ll definitely be buying again and If you are on the border definitely pull the trigger!

B
Bryston Livesay

The embroidery is clean and the hat itself stands out beautifully for something that blends in so well. The quality of this hat is nothing short of top-tier.

T
Tyson Bailey

Love the quality of my hat and all the attention to detail has been amazing!

I
Ike

Love this hat, perfect fit. Fast shipping as well!

I
Ike

Love this hat, fit is perfect and the details are so good.

L
Laura

Love this, please more cuz these hats rock!

K
Keaton Weisz

Great service, great looking hat

A
Anonymous

Great hat! Will be looking to get more!

D
Duffy Counsell

Totally love it! Giddy UP! Ski Bum Cowboy!

A
Alexah

Amazing company!

W
Will Lenhart

The hat is great, it fits well, it looks and feels good, I love the shape. It is exactly what I was looking for, they even mailed it with a handwritten note, stickers, and the coolest matchbox I’ve ever seen. Thank you to the ski bum team.

M
Mason Elliott

My absolute new favorite camp hat. Super solid construction and quality materials. I wear it and my other Ski Bum Cowboy hat everyday and get tons of compliments on them. Creighton and the Ski Bum Cowboys are the best. Can't recommend it enough!!

M
Mason Elliott

My absolute new favorite hat. Super solid construction and quality materials. I wear it everyday and get tons of compliments on it. Creighton and the Ski Bum Cowboys are the best. Can't recommend it enough!!

A
Ally Reid

Such a cool hat! Got so many compliments!

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Janay Standifird

Classic style and fit. Love this brand!

J
Janay Standifird

My teenager is obsessed with this hat!!

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Marissa Meizz

Best piece I will be wearing all year round. The qualityis 10/10