WinMan Logo – Long Sleeve
**Pictures coming soon***
Featuring our new and improved logo, these long sleeve shirts by Next Level are 100% combed ring spun cotton and are incredibly soft.
Hooded Sweatshirt – Est. 2013
Featuring a custom stacked logo and throwback look, this super soft hooded sweatshirt is a must have. WinMan Trails started as a small family project in 2013. Look how far we’ve come!
Hooded Sweatshirt with WinMan Logo
Featuring the classic WinMan logo, this hooded sweatshirt by Next Level is incredibly soft and sure to keep your warm all year long.
2023 Summer Design
This custom design for Summer 2023 represents everything that is magical about the Northwoods. Pair the shirt with one of our amazing leather patch hats featuring the same design and you will be the coolest guy (or gal) in town.
Retro WinMan Logo
Featuring a retro take on our classic logo, this shirt is for everyone who loves to shred dirt.
WinMan Logo
The classic WinMan logo shirt never goes out of style. This is the shirt that should always be in your weekly rotation.
Bike Jump – Long Sleeve
This one is a staff favorite. Inspired by our desire to clear that tabletop we’ve been eyeing all season, we hope this shirt inspires you to send it next time you ride.
Bike Jump
This one is a staff favorite. Inspired by our desire to clear that tabletop we’ve been eyeing all season, we hope this shirt inspires you to send it next time you ride.
2023 Summer Design – Womens
This custom design for Summer 2023 represents everything that is magical about the Northwoods. Pair the shirt with one of our amazing leather patch hats featuring the same design and you will be the coolest gal in town.
WinMan Logo – Womens
The classic WinMan logo shirt never goes out of style. This is the shirt that should always be in your weekly rotation.
Bike Jump – Womens
This one is a staff favorite. Inspired by our desire to clear that tabletop we’ve been eyeing all season, we hope this shirt inspires you to send it next time you ride.
Trucker Hat with Embroidered Logo
The all-new OC771 Ultimate Trucker Cap raises the bar in consistency, fit, and finish. The OC771 features unrivaled comfort & fit, a modern trucker shape, comfort wrapped sweatband, and plastic snapback closure.
Trucker Hat with Leather Patch
The all-new OC771 Ultimate Trucker Cap raises the bar in consistency, fit, and finish. Featuring our Summer 2023 design on a leather patch for the ultimate style.
The OC771 features unrivaled comfort & fit, a modern trucker shape, comfort wrapped sweatband, and plastic snapback closure.
Richardson Low Profile Structured Hat with Embroidered Logo
Classic trucker cap style built with the Richardson quality you’ve come to expect. The Richardson 115 low profile cap has an adjustable snapback and is tailored to fit just right.
Richardson Low Profile Structured Hat with Leather Patch
Classic trucker cap style built with the Richardson quality you’ve come to expect. The Richardson 115 low profile cap has an adjustable snapback and is tailored to fit just right.
WinMan Dad Hat
The tried and true “dad hat” is an unstructured cap made out of garment washed cotton twill. This dad cap features a tuck strap with slide closure so you can adjust it to the exact size you want.
Retro WinMan Logo – Womens
Featuring a retro take on our classic logo, this shirt is for everyone who loves to shred dirt.
2023 Summer Design – Youth
This custom design for Summer 2023 represents everything that is magical about the Northwoods. We hope it inspires your child to get outside and find their next adventure.
Retro WinMan Logo – Youth
Featuring a retro take on our classic logo, this shirt is for everyone who loves to shred dirt.
WinMan Logo – Youth
The classic WinMan logo shirt never goes out of style. This is the shirt that your kid is going to wear every week to school.