How To Wear A Denim Jacket Based On Your Personality

How To Wear A Denim Jacket Based On Your Personality

This guest post is written by Manny De La Cruz, a lifelong fitness enthusiast turned style aficionado. He’s here to help you overhaul your look so you can get more out of life. Follow him on Twitter @WellBuiltSyle and check out his blog.

A common question I get from guys living in warmer climates is what type of outerwear they should wear for the winter season.

Warmer places such as southern California, Nevada, Florida etc., typically don’t get cold enough in the winter to warrant a peacoat or a parka, so guys ask me all the time what I would recommend for someone in their situation. Fortunately, there are several great options, but my favorite by far is the denim jacket. 

What I particularly love about denim jackets is that they can be styled according to your unique personality and taste.

A lot of guys are under the impression that denim jackets are only good if your aim is for a more rugged or blue-collar look. Not true! Depending on how you style the jacket you can wear it as anything from a rugged piece (e.g. with jeans and boots), to a refined or formal piece (e.g. with a collared shirt and tie), to even a rakish piece (e.g. with ripped jeans and a scoop neck t-shirt). Heck, you can even wear it as a sporty piece (e.g. with joggers and sneakers)! It’s really completely up to you. 

I find this “rugged, refined, rakish” framework (hat tip Tanner Guzy over at Masculine Style) particularly useful when I think about styling a denim jacket as it really allows you to tailor a specific look to your personality. 

Not sure how to do this? No problem. Read on below and I’ll explain how. But before I do that let me cover a few details that will help get the most style bang for you buck when wearing a denim jacket.


A denim jacket should fit snug. It’s not supposed to be an overly baggy jacket like a parka or a windbreaker. Here’s an example of the type of fit you want to aim for:


Notice the length of the jacket – it should hit you right around the waist. The sleeves should be slim while the body of the jacket should taper nicely through the midsection (there should still be enough room in the body of the jacket for a decent sized sweater like in the image above). 

An important tip: pop the collar on your denim jacket! It’s my preferred way of wearing it as it adds a bit of confidence to your look. The popped collar also does a wonderful job of framing/highlighting your face, which is exactly what you want your clothing to do. 


If you are a lower contrast male (light hair color + light skin tone) you generally want to opt for a lighter wash denim jacket. 

Conversely, if you are a higher contrast male (dark hair color + light skin tone) a darker wash denim jacket is usually the better choice. 


These are not so much rules as they are guidelines. Many of you will not fit neatly into either the low or high-contrast category (black men, Asian men, men with brown hair and olive skin etc.). Ultimately, it’s how you style the jacket (and its fit) that will make the biggest difference in how well you pull it off.

What To Avoid

Have you ever heard of the Canadian Tuxedo? It’s basically any outfit where you combine a denim jacket with denim jeans. 

All denim looks like this are risky, but they can be pulled off effectively if you make sure to avoid matching the washes of the denim like this:

Instead, make sure the washes differ as much as possible like this:

As you can see, the difference is striking (in a good way). 

Now that I’ve covered some details on how to wear the denim jacket let’s move on to the best way to style one according to your personality. 


First up, rugged style. Here’s an example of how to wear a denim jacket if you’re a more rugged or blue-collar type of guy:

The key to pulling this look off is pairing the denim jacket with other classic rugged pieces like work boots, cable knit sweaters, utility shirts, denim jeans, henleys etc. This is my preferred way of styling a denim jacket and it’s probably the easiest to pull off. If you’re looking for a foolproof way to wear a denim jacket this would be it.  

Next up, refined style. Here’s an example of how to wear the denim jacket if you’re a more suit and tie type of guy (refined or classy):

The key to pulling this look off is thinking about the denim jacket as a substitute for the blazer or sports jacket. A collared shirt is a must for this type of look, but the tie can be optional. In terms of footwear, think quality leather lace ups, loafers, or double monks. Even Chelsea boots or dress boots are a good option. I recommend a pair of crisp chinos or wool trousers to round out the look (cuffed or un-cuffed according to taste).

Lastly, rakish style. Here’s an example of how to wear the denim jacket if you’ve got a more “bad boy” vibe to your personality:

The key to pulling off a more rakish aesthetic with the denim jacket is pairing it with pieces like black denim jeans or ripped jeans, Chelsea boots or Jodhpur boots, and the right types of accessories (in this case a wallet chain). When it comes to rakish style you can really start bending some of the rules. Experiment with unlikely combinations like high top sneakers, hoodies, or drop tail or scoop neck t-shirts.


Almost anything can work here as long as it’s accompanied with a devil-may-care attitude. 

Where To Buy

Lots of retailers are making good denim jackets these days but there are two brands in particular that I recommend more often than all others: Levi’s and J.Crew

What I love about the Levi’s Trucker Jacket ($89.50) is the number of different washes available. This allows you to really dial in a jacket that will work best for your complexion and wardrobe. 

The other option I like is the Stretch Denim Jacket by J.Crew ($118):


The wonderful thing about this jacket is the added elastane/spandex which gives it some stretch making it more comfortable to wear. The drawback, however, is that it only comes in a dark wash. Darn.

Whether you go with Levi’s or J.Crew be rest assured that either option will be a solid addition to your wardrobe.

Final Word

Denim jackets are a fantastic outerwear option for guys who live in climates where traditional winter coats don’t make sense (e.g. southern United States). What makes them one of my favorite options is their versatility. Regardless of your personality or aesthetic there is a look that can work for you. If you haven’t considered the denim jacket before I recommend you give them a shot. I think you will be pleasantly surprised with the results. Here’s to looking sharp!

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