The best menswear essentials are rooted in a sort of timeless crossover between style and utility, functionality and oftentimes, rugged good looks. With its road-ready design, toughness and casually cool style, the trucker jacket sits in the middle of a Venn diagram when it comes to the sort of pieces that make every guy look, well, just plain great.
Like the henley or the humble blue jean, the best trucker jackets are hard-working and straightforward, often boasting details like side hip pockets and button chest pockets. You’ll also find trucker jackets designed and constructed in weather-ready materials, like waxed cotton or sturdy cotton denim.
And in my experience, the best trucker jackets from my favorite brands tend to get better with age, breaking in over time and looking all the better for it. These are my selections for standout style.
In my experience, it’s hard to beat plenty of menswear that comes from the hallowed halls of modern men’s style & gear giant Huckberry. That certainly includes the iconic, often fast-selling Flint and Tinder Waxed Trucker Jacket, which boasts a durable design, a flannel lining and a look that molds to your body over time the more you wear it.
You might call the Flint and Tinder Flannel-Lined Waxed Trucker Jacket a modern style mainstay, available in a wide range of colors and boasting tough sailcloth construction. In my experience, it wears warmly thanks to the flannel lining, while it also breaks in over time and gets better with age.
There’s much to love about the Levi’s Sherpa-Lined Trucker Jacket, one of the original icons of the style itself. Available in the same classic cotton denim fabrication as Levi’s jeans, a cozy lining makes it ready for brisk temperatures and rugged layering.
It’s the details that make the difference when it comes to the best trucker jackets, like contrast stitching, tastefully appointed pockets and durable construction.
KATO gets all of those details right, and then some, offering its Blade Jacket in a wide array of handsome fabrics, from selvedge to waxed cotton.
All things Western style seem to be all the rage right now, and that’s not going away anytime soon. And yet, Wrangler’s outdoor-ready sherpa-lined trucker jacket is about as classic as it gets, with burly construction and plenty of warmth for frigid winter mornings.
What looks like a carefully constructed denim jacket on the outside gets an upgrade with a striped blanket lining from classic Western workwear brand Ariat. It makes a fine pairing alongside inky black denim and sturdy Ariat Chelsea boots.
Taylor Stitch might have started from humble beginnings with a focus on making some of the best men’s shirts, but the Long Haul Jacket is an example of why the brand has built a devout following.
Tasteful touches like a leather logo collar tag, contrasting collars and zig-zag stitching along the front set this jacket apart from the pack.
Luxury meets utility with Billy Reid, the classic-meets-modern brand out of Alabama that exudes confidence and dependable style. Luxe materials and timeless touches like button chest pockets offer the perfect mix of utility and great looks, in my experience.
Leave it to award-winning menswear designer Todd Snyder to offer up his own polished take on a true style icon, done in a uniquely luxurious way.
The Dylan Jacket comes in handsome materials like premium Italian suede for an elevated-meets rugged look.
Filson gear is made for just about anything you throw at it, with all the Pacific Northwest heritage the brand can offer after a century-plus of durable craftsmanship.
The Tin Cloth Short Lined Cruiser Jacket is an expert move for fall and winter layering, in my experience.
In my experience, timeless and traditional menswear pairings just work seamlessly with one another. Take an iconic pair of L.L. Bean “Bean” Boots, style them alongside this trucker jacket and be prepared to take on just about anything across the fall and winter months.
When it comes to the best trucker jackets, construction and toughness make all the difference. This option from the rugged offshoot of Ralph Lauren uses exceptional denim fabric combined with vintage-inspired details that draw on Lee denim jackets from the 1950s.
From its 100 percent American-made construction to details like custom antique brass shank buttons and an oversized chest pocket, Devium takes care of business when it comes to one of the very best trucker jackets on the market. Suffice to say, this under-the-radar brand belongs in your wardrobe.
Corduroy makes for a surprisingly durable trucker jacket, and a sherpa lining takes this affordable mainstay to the next level. Snap chest pockets also bolster your storage space for all of your everyday carry essentials.