Originally published October 17, 2016.
See below for new updates.
I wanted to add a few more looks to this article on how I’m rocking the denim jacket this fall season. The looks feature a mid-wash denim jacket which is a happy medium between light & dark, making it the perfect summer to fall transitional shade.
If you want to watch the video, hit the play button below!
Alright, let’s get this thing started.
LOOK #1: Back To School Denim On Denim
For this first look, I went real casual. It’s a look that I feel appeals to a younger crowd and so I’d recommend it for college students. It’s a denim on denim look that manages to stay far away from Canadian tuxedo land.
Let’s start from the top down. Layered under the denim 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.
Down low, I wanted to give the look a bit of a rugged tune, I went with a pair of Pikolinos boots in a versatile brown color, which I really love because 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 tend to lean towards in the fall.
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.
Why It Works:
If you’re ever going to rock denim on denim, 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 denim 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.
LOOK #2: Invested 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, padded vest. Look 2 is another casual look. It’s hard not to be casual in a denim 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 ensembles.
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.
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.
LOOK #3: Dressed Up Date Night
For the third and final look I wanted to dress up the denim jacket 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 looks feature the Timex Weekender watch with a leather nato strap which gives off a slight rugged vibe.
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.
Why It Works:
The tie with a denim 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 on 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.
Bonus Inspiration—Styled 5 Ways: The Denim Jacket
1) Black on Black on Black
This first look 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!
2) New Business Casual
The second look is a new kind of business casual.
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.
Who says you can’t substitute your trusty blazer for a denim jacket every now and again?
3) On the Edge
The priciest of all the denim jacket get-ups.
On the Edge 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 look 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.
4) Urban Business Class
Look 4 features a darker wash denim jacket.
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. ✈️
5) Slick City Stylin’
Didn’t think I’d end this without throwing in some street style, did you?
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.
That concludes the very first in the Styled 3 Ways series.
Hope that provides you with a little bit of insight and inspiration on the myriad of ways to style 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.
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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