The Denim Jacket: A Men’s Casual Style Staple (How to Wear & Where to Buy)10 min read


If you want to learn a few tricks of the trade on what to wear with a denim jacket, then this article is for you.

How To Wear A Denim Jacket For Men | GENTLEMAN WITHIN

The first 3 denim jacket outfits feature a mid-wash jean jacket which is a happy medium between light & dark, making it the perfect summer to fall transitional shade. I’ll then follow that up with 5 more jean jacket outfits.

But first, let me demonstrate why this jacket style is so versatile.

If you want to watch the video, hit the play button below!

HOW TO WEAR A DENIM JACKET FOR GUYS

HOW TO WEAR A DENIM JACKET | How To Style | Men's Fall Lookbook

Let’s get started.

How To Wear A Denim Jacket With Jeans

Back To School Denim on Denim | GENTLEMAN WITHIN
OUTFIT DETAILS — Jean Jacket: ASOS (similar) | Shirt: Sold Out | Jeans: GAP | Bandana: Amazon | Boots: Pikolinos (alternative 1) | Watch: Timex | Watch Strap: Benchmark Straps | Bracelets: Steve Madden | Lapel Pin: Ties.com

For this first look on how to style a denim jacket, I went real casual. It’s a look that I feel appeals to a younger crowd and so I’d recommend it for high school or college students. It’s a denim on denim look that manages to avoid a dreaded Canadian tux aesthetic.

Let’s start from the top down. Layered under the jean jacket is a flannel shirt with a plum check pattern, another color that’s seasonal appropriate. Since this is a younger look, I hopped on the trendy neckerchief trend and wrapped an olive bandana around my neck. I thought it looks cool, is stylish and if you pull it off correctly you won’t end up looking like a boy scout.

For the pants, I went with a pair of slim, selvedge, dark wash denim with a thin jean roll to show off the ubiquitous chain stitching detail. It is cuffing season after all.

Brown Pikolinos Boots | GENTLEMAN WITHIN
DETAILS — Jeans: GAP | Boots: Pikolinos (alternative 1)

Next, I wanted to add a bit of ruggedness to the look and so I went with a pair of Pikolinos boots in a versatile brown color. I love that they’ve got a moc toe and give off those work boot vibes, without the bulk of a work boot. The slimmed down silhouette makes it ruggedly refined which is a style I’ve been leaning towards lately.

And finally, (not seen in the image) in the video above, you will see that I’m wearing quite a few bracelets. My thinking was that this is a really casual look and I wanted to go all-in with a wrist-full of accessories, something I normally wouldn’t do.

Denim On Denim Look | GENTLEMAN WITHIN
OUTFIT DETAILS — Denim Jacket: ASOS (similar) | Shirt: Sold Out | Jeans: GAP | Bandana: Amazon | Boots: Pikolinos (alternative 1) | Watch: Timex | Watch Strap: Benchmark Straps | Bracelets: Steve Madden | Lapel Pin: Ties.com

Why It Works:

If you’re ever going to wear a denim jacket with jeans there’s one rule to keep in mind. The washes should have enough contrast making the fact that you’re rocking denim on denim an afterthought.

With this look, it’s hard to tell that I’m even wearing denim jeans with a jean jacket. If you’re too monochromatic here, you’ll be giving off more of a Brokeback Mountain vibe, which is to be avoided at all costs.

Shop AE Denim Jackets

How To Layer With A Denim Jacket

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Invested In Layers | GENTLEMAN WITHIN
OUTFIT DETAILS — Denim Jacket: American Eagle, Everlane | Shirt: J.Crew | Pants: Chinos | Vest: J.Crew Factory | Boots: Thursday Boots Co. | Watch: Timex | Watch Strap: Benchmark Straps | Belt: Anson Belt

It’s time to invest in layers. Sorry for the lame pun, but fall means layers and you can really benefit from investing in a few staple layering pieces such as a henley or light quilted vest. This outfit is another casual look. It’s hard not to be casual in a jean jacket.

Up top, I’ve layered a light, quilted burgundy vest over a window pane patterned button down (get a closer look in the video above) and the denim jacket over top of the vest. For fall, I really like burgundy and olive and so those are two mainstays in many of my fall outfits.

For the pants, I went with slate gray chinos which is appropriate for fall and will compliment many other autumnal colors. The shoes I’m wearing are the ever versatile chukka boot in navy suede, a must have for any stylish man this fall.

Denim Jacket Layered Up Look | GENTLEMAN WITHIN
OUTFIT DETAILS — Jean Jacket: American Eagle, Everlane | Shirt: J.Crew | Pants: Chinos | Vest: J.Crew Factory | Boots: Thursday Boots Co. | Watch: Timex | Watch Strap: Benchmark Straps | Belt: Anson Belt

Why It Works:

A denim jacket is inherently casual and lends itself to being layered over or under other stylish staples. With this look the neutrals are livened up by the richness of the burgundy vest.

Shop J.Crew Factory Vests

Review: American Eagle Flex Jean vs Express Hyper Stretch Jean (Battle) | GENTLEMAN WITHINRelated: You might like this review of American Eagle and Express Jeans.

How To Dress Up A Denim Jacket

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Dressed Up Date Night | GENTLEMAN WITHIN
OUTFIT DETAILS — Denim Jacket: American Eagle, Everlane | Shirt: J.Crew | Pants: UNIQLO | Shirt: Uniqlo (similar) | Boots: Thursday Boots Co. | Tie: eBay | Tie Clip: The Tie Bar | Watch: Timex | Watch Strap: Benchmark Straps | Belt: Anson Belt | Sunglasses: Warby Parker

For the third outfit on how to style a jean jacket, I wanted to dress it up ever so slightly. This is achieved by the addition of a dotted, burgundy, knit tie over a navy corduroy button down (noticing a theme yet?).

Style guys often say to wear darker colors down low and lighter colors up top. And while this is a good general rule of thumb as it draws people’s attention up towards your face, you can pull off the opposite if you have something to grab their attention up high, like a rich burgundy tie with a tie bar for example.

Again I’m playing with the neutrals of navy, tan and brown with a pop of burgundy from the knit tie. All 3 outfits feature the Timex Weekender watch with a leather nato strap which gives off a slight rugged vibe.

Navy Suede Chukka Boots | GENTLEMAN WITHIN
OUTFIT DETAILS — Pants: UNIQLO | Boots: Thursday Boots Co.

Down low, I’m back at it with the navy suede chukkas. That’s the beauty of a pair of shoes like this. They can be worn slightly more dressy and slightly more casual just the same. It’s a highly versatile shoe worth investing in.

Date Night Denim Look | GENTLEMAN WITHIN
OUTFIT DETAILS — Denim Jacket: American Eagle, Everlane | Shirt: J.Crew | Pants: UNIQLO | Shirt: Uniqlo (similar) | Boots: Thursday Boots Co. | Tie: eBay | Tie Clip: The Tie Bar | Watch: Timex | Watch Strap: Benchmark Straps | Belt: Anson Belt | Sunglasses: Warby Parker

Why It Works:

The tie with a jean jacket look has been one of my smart casual go-to’s for a while now. The reason I love it so much is because you can wear it for a night out in the city with the boys or out to a date with a special lady. It’s casual, but refined. You won’t be overdressed, but still be dressed a notch above everyone else.

Shop Everlane Denim Jackets

Quick note: If you’re enjoying this article on how to style a denim jacket, then you’ll probably find my other writing on all things men’s style useful. Each week, I share updates, style tips and other things not shared on the blog through my free email newsletter.

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DENIM JACKET OUTFITS FOR MEN

Styled 5 Ways: The Denim Jacket | Gentleman Within

How To Wear A Black Denim Jacket

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Black on Black - Styled 5 Ways | The Denim Jacket
Urban Outfitters denim jacket | H&M t-shirt | Dockers alpha khaki | Levis canvas sneaker | Smartwool ultra light socks | Warby Parker sunglasses

This next outfit on how to wear a jean jacket features ‘all black everything,’ shout out to Young Hov. It’s clean, it’s ultra-casual, it’s sleek. A little bit of confidence goes a long way in pulling this ensemble off. But you got this!

The rule of thumb is to keep everything dark and monochrome. It’s edgy for sure and one of the easier ways to wear a jean jacket.


How To Wear A Denim Jacket For Business Casual

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New Business Casual - Styled 5 Ways | The Denim Jacket
Levis denim jacket | Brooks Brothers oxford shirt (ocbd) | Saks Off 5th Avenue wool trousers | Suitsupply double monk strap shoes | Tiebar herringbone socks | Zomake shoe horn

This next outfit is a new kind of business casual. It’s dressier and more refined for sure, but actually works quite well. Who says you can’t substitute your trusty blazer for a jean jacket every now and again?

It’s what many style bloggers would a call high/low approach. In that it features some pricer, more refined pieces like the wool trousers, and suede double monk straps, paired with the more casual mid-wash denim jacket, and tweed necktie.


How To Wear A Denim Jacket With Flannel

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On The Edge - Styled 5 Ways | The Denim Jacket
Nudie Jeans denim jacket | Neighborhood flannel shirt | AG Jeans faded denim | Thorogood leather boots | Bespoke Post weekender bag

Here’s another way that you can wear the controversial denim on denim trend. This outfit features items from Mr. Porter, a fine menswear site might I say. If money were no issue, it would definitely be my go-to for a new wardrobe.

This fit is cool and rugged. The distressing on the jacket and jeans exudes a casual attitude. While the flannel shirt pairs nicely with the black boots.

All you’ve got to do is roll up your jeans, grab that slick mason bag, a you’re off for the weekend in style.


How To Wear A Denim Jacket With A Tie

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Urban Business Class - Styled 5 Ways | The Denim Jacket
Levi’s denim jacket | Uniqlo oxford shirt (ocbd) | J. Crew broken-in chino | Anson Belt & Buckle leather belt | Calvin Klein wingtip oxfords | Boardroom Socks dotted socks | Fortunatever denim necktie

Now this next outfit features a darker wash denim jacket from Levi’s. This is how you can wear a jean jacket with a tie. Just like my stance on jeans, if I were to recommend one ‘jean’ jacket, it would be dark wash of course.

I love the denim jacket as a layering piece, too. It can be worn over top of a clean oxford cloth button down and a textured tie. With this get-up, you see that the pants are light, while the jacket is dark. In menswear, contrast is a good thing.

The dotted socks add a fun statement to an otherwise very simple outfit. Finish off the look with a pair of navy, suede wingtips and a customized leather belt and you’re ready to jet set. ✈


How To Wear A Denim Jacket In Summer

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Slick City Stylin - Styled 5 Ways | The Denim Jacket
ASOS denim jacket | Ralph Lauren dress shirt | Saks Off 5th Avenue straight-leg jeans | H&M desert boots | Boardroom Socks striped socks | Ray-Ban sunglasses

Didn’t think I’d end this without throwing in some street style, did you? This is how to wear a denim jacket as a rule breaker. It’s the perfect way to wear a denim jacket in the summer. Keep it light!

What I love about this look is that it breaks the rules. Of course you want to know them before you break them.

A rule of thumb is that you want your jacket to contrast against your pants. Darker jacket, lighter pants, and lighter jacket, darker pants.

That rule is thrown out the window with this get-up.

Why does it work?

The blue shirt provides a nice contrast against both the jacket and jeans. The dotted pattern makes it even bolder, so the eye is drawn to the shirt first.

One of my favorite pattern combinations is dots and stripes. There’s just something aesthetically pleasing about it. So these striped socks are a great match with dotted shirt. Top off the look with a pair of gray, suede chukka boots and clubmaster sunglasses and you’ll be one cool cat.


denim jacket styled collage

Here you can check out more How To Style articles. I hope that provides you with a little bit of insight and inspiration on how to wear a denim jacket. It really is a style staple that’s as versatile as any garment out there.

Before you go feel free to check me out on Instagram for more daily style inspiration.

Originally published on October, 2016.

On to you, which look in this series is your favorite?

Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.

Looking forward to seeing you in there.

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