You don’t have to be a haulier to get a lot of mileage out of a trucker. Or a cowboy. The jean jacket has, like a lot of workwear staples, gone from being a beat-up old-reliable of menswear to a go-to for more dress codes than you’d imagine. But what do you pair with a denim jacket besides… More denim? That’s where this guide to jean jacket outfits comes in.

“A denim jacket is a fantastic option to have at your disposal for its versatility, especially at this time of the year,” says Daniel Rhone, stylist and personal shopper for a squad of top, top Premier League footballers – emphasis on ‘ballers’. “I like to layer one as a middle tier between my choice of outerwear and an underlayer of a tee or shirt. Particularly if I’ve underestimated the temperature outside.”

You don’t have to take his word for it, although you should, because he’s a very cool guy, even when he wraps up warm. But to drive the point home, here are 10 different ways to wear a jean jacket so that you can keep on trucking down the road.


You’re effectively wearing jeans on your top half, and you know that double denim is dangerous territory. But so is going out half-naked. Enter chinos. They can be smart, with formalising features such as pleats, creases and a tab closure, but they can also be casual.

Their military history and typically utilitarian cotton-twill fabric nevertheless make them a dependable denim ally; the original khaki – technically a colour, not a style – is a classic pairing. Add a white T-shirt (see below) and you’re Don Draper at the weekend.


This is another classic pairing enshrined in Americana. A crisp but fuss-free look, it’s not quite as easy as you might think.

Its success largely hinges on finding the perfect white tee, which can be a Goldilocks-ian quest: not too slim, not too baggy; not too translucent, not too bulletproof; not too “gunny”, not too modest; not too much like a dress, not too much like a crop-top; not so high on the neck so that it’s an undershirt-cum-garotte, not so low that it’s a clavicle-exposing deep-U.

Whoever called the white tee a basic was wrong.


A denim jacket doesn’t exactly fall under the category of sportswear, unless you’re a rodeo rider. But it provides a degree of structure to offset the softness of your joggers, as well as more prosaically just not being another piece of jersey, thereby saving you from having to go full tracksuit or ‘Tesco tuxedo’.

This isn’t a hard-and-fast rule (there aren’t many of those left in menswear) but you’re probably best to steer clear of cowboy details on your denim jacket. Style historians don’t record athleisure as having been a key trend in the Old West.


Double denim can be doubly good even if you flagrantly transgress the ‘distinct shades’ rule: see Martin Sheen in Badlands. It can also be very, very bad: see Justin Timberlake in your nightmares. But for a fail-safe way to splice jeans, black and blue is hard to beat.

Other colours of jeans can do the same trick: grey, for one, and even white, although that presents its own pitfalls, not to mention impracticalities. But like Wesley Snipes having a cheeky flutter on the Rugby World Cup, always bet on black.


A shade more difficult than black jeans, but still not that hard, unwashed indigo denim will stand much less of a chance of optically bleeding into a lighter and/or distressed denim jacket than lighter and/or distressed jeans, for reasons that should hopefully be apparent from reading this sentence.

It’s not like double, indistinguishably dark denim can’t ever be done, mind: we seem to recall Ryan Gosling looking fairly badass in Drive. But that said, he is Canadian, so may possess a home country advantage.


Yes, you can mix business with workwear. Make the partnership less what-the-hell by dialling down the dressiness of the other elements to bring them more in line with your decidedly casual trucker: a button-down Oxford instead of a stiff-coloured poplin; a knitted tie instead of woven silk; chinos instead of tailored trousers (although they can work too – see below).

N.B., even if your denim jacket isn’t overly faded, it’s still way more informal than any tailored equivalent, so may not be SFW at your place of employment.


This combo is a fallback for any menswear blogger attempting to look vaguely urban. Don’t let that put you off. A hoodie is a natural sparring partner for a denim jacket because they’re both low-key, chuck-on weekend staples.

In that vein, don’t overdo it. Keep the colours neutral and don’t go too boxy with the fit of the hoodie. Avoid the brash logos of streetwear’s latest drops and stick to a navy or grey marl under a blue denim jacket.


Similar to the shirt and tie, it helps if you can minimise the seeming discord between your casual jacket and smart trousers. That could be by jacking your jacket up in smartness with an unwashed dark denim, plus minimal bells and whistles such as contrast stitching or rivets.

Likewise, you could pull your trousers down a notch in formality with a more substantial, nubby material that’s closer to denim on the spectrum. Or opt for a relaxed fit, a cropped length or turn-ups.

how to wear a denim jacket with tailored trousers


Anywhere you can wear a shirt, you can rock a roll neck. Well, pretty much. But before you knit up, consider your denim jacket’s finish, whether pristine indigo or battered stonewash, and how that metaphorically stitches together with your jumper.

If the latter’s too sheer and sheeny, there might be a dissonance with the rough, tough denim; too chunky and your jacket might appear insubstantial by comparison. (Generally speaking, layers should get thicker the further away they get from your body, and vice versa.)


As with a tailored blazer, your denim jacket should be slim fitting if you want to wear it under an overcoat. You should just about be able to get two fingers down it when done up and it should be narrow-necked so it doesn’t compete with your coat’s lapels.

By its nature, even the smartest tailored outerwear has a degree of ruggedness so this is not as incongruous as you might think. Don’t be afraid to juxtapose, either: camel, which normally skews formal, can be a really nice combo. Bonus points if your jacket’s stitching matches the colour.