Denim Jacket Outfits: Five Easy Ways To Wear One

by Beau Hayhoe  |  in Casual Style

Have you seen our other Five Ways To Wear One articles?


Got a great denim jacket and need to put together a few outfits? Searching for a couple ideas? Well, look no further. We’re putting together five easy denim jacket outfits for men in this article. We’ll be featuring a dark jean jacket, but you an easily sub in a medium stonewashed jean jacket, if that’s more your style.

As much as I love the changing seasons and fall and winter layering, it’s a relief to get back to more moderate temperatures when early spring hits. That means certain pieces come back into the rotation, and some go in storage. I’ve found there’s one item I somehow manage to find a way to wear nearly year-round: my trusty denim jacket.

No matter the season, I can always layer it up in winter or rock it with lightweight chinos in the summer.

There’s likely a good reason for that, the same reason why the traditional style and silhouette has endured—with twists and turns—through so many decades. It’s timeless, it’s rugged and the best ones are built to last (quite like your favorite pair of dark denim, actually).

It’s a piece that’s a favorite of rockers and movie stars alike, and its classic workwear roots give it an authenticity that continues to evoke great stories. So it’s no surprise that several brands continue to dish up their take on the style.

A Little About The Denim Jacket In These Outfits

The great thing about such a classic piece is that brands have reworked the style as they see fit, while still keeping the basics in place. Take, for example, Rogue Territory.

The jacket you see in the outfits below is made from sturdy selvedge denim like other great denim jackets, yet it incorporates unique styling touches like a slanted middle buttonhole.

Beware that the Rogue Territory jacket is dyed with indigo, so that blue color will likely rub off on some surfaces.

Other Denim Jacket Options

Given the materials and quality, something like that Rogue Territory jacket definitely falls on the premium side of things. That doesn’t mean other more affordable brands are forgoing the style.

Another thing to note: While light wash denim jackets are out there (and they do have a time and place) go on the hunt for a more versatile, cleaner dark denim or medium blue denim jacket. We’ve listed a few of our favorite options below.

Everyone from J. Crew to Old Navy is offering up their take on the silhouette, so there are definitely options to go around. And as you’ll see below, there’s certainly no shortage of ways in which to style this piece. Care for it properly, and it’ll last you even longer.

How Your Jean Jacket Should Fit

Given the shifting dress codes of the modern office or the classroom, a denim jacket can be worn and accessorized just about any which way you please (sans highly formal or traditional events, of course).

That means you should look for one that roughly mirrors the fit of your favorite blazer up top — trimmer sleeves that hit right about at the wrist and a fitted (but not overly tight) cut through the shoulders. Lengthwise, the jacket should hit right above your waist.

In a dark color and the proper fit, it’ll pair just as easily with a tie as a henley (more on that in a minute).

How To Care For Your Denim Jacket

As to care, some would argue you should treat it like raw denim — that is, wear it as long as possible before washing.

There are denim experts out there who can offer up plenty of insight, but the best rule of thumb would be to spot-clean it regularly, spraying with Febreze and airing out if you don’t wear it all that frequently.

If, however, you rock it a bunch and decide it needs a good wash, it’s best to wash it either on its own or with like colors (namely dark blues) and minimal detergent, and hang-dry it.

Note that if you’re the type to break denim in and look for fades to develop in the indigo dye, washing it accelerates that fading process faster (and your unique creases won’t develop as deeply).

It’s a learning process, but if this is your first time rocking a denim jacket, you’ll gain a feel for when it could use some TLC.

Got all that down? Ready for those outfits? Read on.

#1. Everyday Essentials

Denim Jacket outfits with chinos and a white shirt

Starting out wearing a denim jacket can be a little intimidating, particularly if you’re not used to the style (it certainly took me a while to get used to it). But that intimidation factor can be avoided by subbing in the denim jacket in place of a navy blazer or bomber jacket in a four-season outfit.

The slim chinos and that brown leather watch are tried-and true classics at great prices, and those captoe boots are a true knockout from an excellent brand.

The white Oxford is a style essential in its own right, and the denim jacket gives the whole thing it a bit of rugged edge — plus, the red striped socks are made in America and add a solid shot of color to the whole thing.

#2. Rock N’ Roll Throwback

Dark blue jean jacket with black jeans

Outfit number two here just might be the most common thing we think of when talking denim jackets, at least in modern times. The denim jacket’s rugged flair has been a natural fit for rebellious rockers, but you don’t have to hang out in dive bars to channel some of that energy.

Easygoing staples like an American-made pocket tee and slim black denim (also made in the States) do some of the legwork for you.

Wary of the denim-on-denim look? Unlike pairing dark jeans and a dark denim jacket, the indigo and black here play off each other well enough to avoid the dreaded Canadian tuxedo.

Finishing things off with some simple-yet-sturdy black boots and socks with a pop of color keeps things minimal and not too over-the-top.

#3. Versatile Layering

denim jacket outfits with grey chinos and a chambray shirt

A denim jacket also works quite well alongside pieces that have a classic-yet-vintage vibe — like the off-white sweatshirt you see here. Paired with an ever-reliable chambray shirt and slim grey chinos, it’s a great way to play cooler shades of color off each other.

The dark blue works well with the lighter shade in the chambray shirt, and the off-white of the sweatshirt (an investment-worthy piece in its own right) works with the light grey chinos.

And when you work in sleek brown boots and a classic, crisp watch, you’ve got yourself a combo that really can’t be beat—for the office on a casual Friday, for a weekend exploring your local park or for some travel on the open road.

#4. Traditional and Tailored

jean jacket with olive chinos

Outfit number four here really works off the principle that a well-cut, dark blue denim jacket can work just as well as a navy blazer. A charcoal Oxford from the always-reliable folks at Taylor Stitch (or whatever white or grey Oxford you’ve got in your closet) grounds the pindot tie and olive chinos nicely.

If you’ve never thought of pairing olive and navy together, give it a shot — both are rich, four-season colors that can deliver some pop in the fall or winter while playing it cool in the spring and summer.

Tan suede Chelsea boots are a bit of a swerve from brown wingtips (although you could also wear those). The great thing about using a denim jacket in place of a blazer is the fact that you can dial back your accessories appropriately — hence the use of a classic brown leather watch again.

#5. Summer-Ready

denim jacket with slim khaki chinos and a grey short sleeve shirt

Lest you think that a denim jacket is too heavy to wear in the summer, there are still ways to rock it — on days when it’s not overwhelmingly hot, that is.

The best approach would be to keep things simple — a contemporary, slim-cut short-sleeve shirt helps out with the heat (and looks sharp, too), while the tan jeans are a nice change of pace from light wash or black denim.

The built-in stretch of that denim certainly works well in terms of comfort, too. Finishing things off with a sharp pair of white leather sneakers keeps the outfit summer-friendly, while a classic Timex grounds the whole look casually, too.

The sturdy nature and versatile color of a denim jacket makes it easy to pair with all sorts of combinations, from sharp looks to rugged, rocker-ready ensembles. If you grab one that fits properly, it can function as both outerwear and a cool blazer substitute.

Perhaps the biggest upside is that it’ll break in over time and develop a story that’s as unique as the adventures and travels you’ll have while wearing it.

Like these denim Jacket Outfit Ideas?

Out of the five denim jacket outfits we put together here, which one is your fave? Any awesome outfit ideas you’d like to share with us? Hit us up on Instagram anytime.

What’s changed?
01/29/2023Updated text and links
11/18/2020Updated text, added / updated links
03/16/2016Original publish date