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  • Writer's pictureDavid Connolly

Utility Player - 5 modern ways to wear a Trucker Jacket

Updated: May 28, 2021

Model in Trucker Jacket

When he knows how to wear it, a denim jean jacket can be one of the most powerful weapons in a man’s sartorial arsenal. A heavy-duty workhorse that can be teamed with anything from tailoring to trainers and a hoodie, it’s one of the most versatile pieces of outerwear there is.

In spite of this, many men give it a wide berth for the simple fact that styling one can present something of a challenge. Get it right and you’re Ryan Gosling, casually striding through the airport on your way to Cannes Film Festival. Get it wrong, however, and you’re the cowboy from Village People. Unfortunately, there’s not a great deal of middle ground.

In order to help you avoid looking like the latter when you don your denim, we’ve taken it upon ourselves to give you a crash course in how to pull off one of menswear’s most timeless garments.

Timeless Ways To Wear A Denim Jacket

Double Denim

Model double denim Trucker Jacket

If you were to brainstorm a list of the cardinal sins of menswear, pairing denim with denim would no doubt feature early on.

This is a common misconception. While it’s true that doubling up on your denim is no easy feat, it can be done – and when done right it’s one of the most powerful style moves a man can make.

Nailing this trending look relies on balancing the shades of your denim. Unless you’re attempting to make a statement, it would be inadvisable to pair like with like – stonewash jeans and a stonewash jacket, for example. Instead, mix your shades up. Dark raw jeans down below and a darker wash up top is a safe place to start.


Model Sherpa Trucker Jacket

Given that the denim jacket (and all denim clothing, for that matter) was born with manual labour in mind, it only seems fitting that it should be in its element when worn as part of a workwear-inspired outfit.

Quality and ruggedness is the name of the game here. You want to match your denim jacket with garments that not only look good, but that will still be hanging proudly in your wardrobe for decades to come.

Try styling a borg collar denim jacket with a thick flannel shirt. You could even wear them open, layered with a plain white T-shirt underneath. On the bottom, go for dark, selvedge jeans in a regular, straight leg. Finally, slip into some sturdy leather boots and you’re good to hit the workshop… or just the pub.

With Tailoring

Model tailored Trucker Jacket

No, we haven’t gone completely mad. Contrary to popular belief, a denim jacket can be worn with tailoring. More specifically, tailored trousers. This look gives a new meaning to the term “smart-casual”, in that it is quite literally, smart on the bottom and casual up top.

This will work best with a dark denim jacket – think black, grey or raw. Slot a black roll neck or crew-neck jumper underneath and finish your upper half off with some optional accessories: a quality pair of shades, a fisherman beanie, or even both.

For the “smart” part, chose charcoal wool trousers with a slim leg. Factor in some pleats for extra cool points. Last but not least, slip on a pair of black leather Derby shoes to tie the look together.

Weekend Casual

Model Casual Trucker Jacket

Experimenting with tailoring and workwear is all well and good, but where the denim jacket really comes into its own is as part of your weekend wardrobe. This is, at its core, a piece of casual clothing – meaning its right at home with most of your everyday garments.

During the warmer half of the year, team a mid-wash trucker jacket with a plain T-shirt and cuff the sleeves. Then grab a pair of chinos (navy or beige are both solid options) and tie it together with minimal white sneakers.

All-Black Everything

Model Black Trucker Jacket

Having been picked up by many musical subcultures – punk, metal and greasers to name just a few – the denim jacket has become something of a rockstar itself, and what could be more rock ‘n’ roll than dressing head to toe in black?

Going all black is a look that’s never going to go out of style and has the added bonus of being extremely slimming.

Starting from the bottom up, arm yourself with a pair of black leather Chelsea boots and some slim-fit jeans in a black or charcoal wash. Next, pull on a black tee or shirt (depending on the occasion) and throw your black denim jacket over the top. So easy, you could get dressed in the dark.

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