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.

Double Denim

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 lighter wash up top is a safe place to start.

Blue Collar

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

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 sunglasses, 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

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

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.

Ivy League

While denim isn’t exactly one of the cornerstones of Ivy League style, the two do have a historic relationship. During the 1960s, protesting college students began wearing jeans and denim jackets as a token of solidarity with the working class – those most affected by racial discrimination and the war draft.

While the reasoning behind it has been mostly forgotten, the denim jacket does still have a place within American collegiate style. And that means it can work well as part of an preppy-inspired outfit.

The trick lies in the layering. Depending on the season, a dark-wash denim jacket can serve as either a light outer layer on top of a crew-neck jumper and Oxford shirt, or as a mid layer beneath a puffer jacket or parka. Top it off with a pair of token khakis and suede shoes or canvas sneakers.

Sea Stripes

A denim jacket may not be the most practical outerwear option for your next sailing trip but we’d be lying if we said it didn’t look the part when teamed up with a few sea-faring favourites.

Wash-wise, anything bar white will work well here. Generally speaking, the darker the jacket, the dressier it looks, so reserve stonewash for casual affairs and roll out the black, raw and mid-wash when things need smartening up a little. Overall, the goal is to stick to a palette based on blue.

In terms of legwear, opt for white or cream (which is why white is off limits in the jacket department) and use a Breton top to bring the maritime feel to life. When it comes to footwear it’s really a matter of personal preference but boat shoes would seem to us to be the obvious choice.

Stuck In The Middle

There are countless reasons to love the denim jacket, but one of the key ones is its layering excellence. A good one can work as a light jacket in warm weather, a rugged top layer in transitional conditions, and as a mid layer when the weather really takes a turn for the worse.

The denim jacket’s low-profile fit and cropped design make it perfectly suited for throwing on over some knitwear, or even just a T-shirt and slotting underneath your big winter coat.

For a fail-safe look that won’t go out of style, layer with classic pieces like a wool overcoat and a plain white tee. To keep things traditional, stick to some form of indigo for the denim jacket but make sure there’s sufficient contrast with the legwear if you’re going to wear jeans.

In Transition

Any time of the year is a good time for a denim jacket, but if there’s one type of weather in which this outerwear classic really excels, it’s that awkward period of uncertainty between seasons.

Lightweight layering is the way to get around it and a jean jacket is unrivalled as a sturdy outer layer. Just make sure it’s roomy enough to slot a couple of pieces underneath.

Start off with a base layer like a long-sleeve T-shirt and build upon that with things like fine-gauge knitwear or a lightweight down vest. Chinos are a safe bet in terms of legwear, avoiding any tricky double denim scenarios.

Denim Jacket Twist

Picture a denim jacket. Chances are, the garment you’re now envisaging is the style known as a “trucker”. While it is true that this type of denim jacket is the most widespread, it’s by no means the only option and branching out is a great way to put a contemporary spin on a classic look.

So what other styles are there? Well, as far as we’re concerned, the key one to consider is the overshirt. It’s cut longer than a trucker in the body and is lighter in weight, making it excellent for layering.

There are a thousand different ways to wear a “shacket”, but we like to dress it up with smarter pieces. So, add a touch of elegance to a traditionally blue collar fabric by teaming it with slim-fitting legwear, loafers and a well-fitting shirt.

The White Stuff

If you’re still concerned about venturing into the world of double denim, there is one foolproof way to always get it right: take the contrast between top and bottom to the extreme by using a white denim jacket.

Once you have a well-cut white denim trucker jacket, the next thing to consider is the colour of your legwear. Stay away from bright colours or pastels and instead stick to deep, dark shades like navy, forest green or black. When it comes to footwear, some white sneakers can help give the jacket some context within the overall look, or match the shoes to your legwear, leaving the jacket to serve as a statement piece.