Skip to main content
  1. Home
  2. Fashion & Style
  3. Evergreens

You Don’t Have to Drive an 18- Wheeler to Rock these Cool Trucker Jackets

We’re in favor of building out a well-stocked menswear rotation of seasonal must-haves. And one of those seasonal must-haves is the trucker jacket. 

After all, having a closet filled (within reason) with unique, timeless pieces pays dividends in the long run. We’d say it’ll even give you joy, but that’s just us.

Recommended Videos

So, the best trucker jackets for your consideration offer up something different than a run-of-the-mill windbreaker for the winter-to-spring transition. The trucker jacket was built with hard work and the open road in mind, so today’s crop features reliable construction and unique detailing (like an above-the-waist cut and a slim fit).

There’s a price point and a style for everyone, so you best get to work.

Best Trucker Jackets to Buy Now

Buy at Amazon
Image used with permission by copyright holder

Here’s the brand that practically started it all when it comes to America’s love affair with denim — and therefore also the trucker jacket. This iteration of the trucker jacket is different from what you might call a “denim” jacket because of the detailing, including slanted stitching down the chest and a point collar. With those details in mind, the Levi’s Trucker Jacket is one of the best trucker jackets you can buy now. It’s a pioneering style staple to this day.

Buy at Amazon

Buy at Amazon
Image used with permission by copyright holder

Another crucial point to remember when shopping the best trucker jackets – they’re not all made of denim. Case in point: The Orvis Highpoint Trucker Jacket, made with a cotton blend designed to resist wind and rain. It’s the perfect jacket to wear as we transition into spring, especially given its neutral, but outdoorsy colorway.

Buy at Amazon

Buy at Huckberry
Image used with permission by copyright holder

The trucker jacket gets a rugged return to form here with this sherpa-lined iteration featuring the timeless “Type 3” silhouette (first pioneered by brands like Levi’s). This take on the trucker jacket is American-made, and it’s perfect for chilly late winter and early spring days.

Buy at Huckberry

Buy at Topo Designs
Image used with permission by copyright holder

What makes the Topo Designs Trucker Jacket more than just your average denim jacket? It comes down to the details, such as the above-the-waist cut and the large chest flap pockets, more common in trucker jackets than plain old denim jackets. The fact that you can get this rugged number from the same brand that makes your favorite daypack and field pants is an added bonus.

Buy at Topo Designs

Buy at Filson
Image used with permission by copyright holder

It makes sense that the trucker jacket in its various iterations would be done particularly well by the Pacific Northwest style purveyors at Filson. The Tin Cloth Cruiser Jacket is a water-repellent take on the trucker, able to block water, wind, and rain. Wear it with tough chore pants, a thermal henley, and leather work boots the next time you need to get the job done.

Buy at Filson

Buy at NORDSTROM
Image used with permission by copyright holder

If you want to dive headfirst into the whole trucker jacket game, you might as well go all out with this handsome vintage-style trucker jacket from lauded outerwear brand Schott. It features genuine sheep shearling lining (and yes, an expensive price tag).

Buy at NORDSTROM

Beau Hayhoe is a freelance men’s style writer, consultant and PR pro based in Brooklyn. Beau’s menswear and gear writing has… Read Full Bio
The Gentleman’s Guide to Wedding Attire
Wedding toast

As a menswear writer, I take pride in snazzy dressing. You can imagine my chagrin when I showed up to a recent wedding as the worst-dressed groomsman. It had been a perfect storm of sartorial mishaps. I’d slimmed down since the last time I wore black tie, leaving the jacket and cummerbund baggy. My favorite cuff links had vanished on a work trip. To complete the fiasco, my tuxedo shirt bore an archipelago of merlot stains from a Christmas party in late ’25.

Fortunately, I had the chance to salvage my dignity at another wedding a few weeks later. I rallied like Rocky. Rush alterations. New cuff links. A crisp Marcella shirt. Polished black shoes. I went from disheveled schlub to black-tie stud.

Read more
TAG Heuer just brought back its best Japanese racing collab
Watch, Dial, Logo

TAG Heuer just announced the second Carrera collaboration with Team Ikuzawa and Bamford Watch Department, three years after their first one together — and this time, they went back to a stopwatch.

The watch is built on TAG Heuer’s 39mm Carrera Glassbox, the modern take on the original 1963 Carrera that swaps a bezel for a highly domed sapphire crystal. But the design here pulls specifically from the Heuer Roadmaster, a vintage timing stopwatch Team Ikuzawa used trackside through the ’70s and ’80s, not from any particular car or race.

Read more
Celebrate the 80th anniversary of Ferrari in Boca Raton this winter
Machine, Spoke, Alloy Wheel

Gearheads and luxury car enthusiasts will be descending on Florida on February 19th through the 21st as the Cavallino Classic looks to return to Southern Florida for another edition. A collection of some of the most iconic Ferraris from every era is expected to be on display for the three-day event meant to showcase a century of craftsmanship and artistry. Even better, the event has a little extra throttle this year as it celebrates the brand’s 80th anniversary.

We measure our programming by whether it gives Club members and resort guests something they cannot find anywhere else. Cavallino Classic does that. It is not only for collectors and enthusiasts. It is for anyone who appreciates rare craftsmanship and a weekend built around it – Daniel Hostettler, President & CEO of The Boca Raton

Read more