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How to style a jean jacket: The ultimate guide to a denim favorite

Learn how to wear a jean jacket like James Dean and Bruce Springsteen

When Levi Strauss created the denim jean in the 1870s, he didn’t wait long to capitalize on the incredible runaway success by making the top half of the ensemble with the denim jacket ten years later. As American as biscuits and gravy, the denim jacket became a staple in our nation’s fashion, symbolizing rebellion and individualism. But learning how to style a jean jacket is crucial to owning one.

From James Dean capturing the rebellious American spirit in Rebel Without a Cause to “The Boss” himself, Bruce Springsteen, the denim jacket endured decades of fashion by constantly reinventing itself and maintaining its originality. If you feel a slight sense of intimidation going up against the likes of Dean or Springsteen when trying to wear one, below is a guide to help you bring the timeless classic to life in your own wardrobe.

Man in denim jacket
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What pants do you wear with a denim jacket?

Denim jackets are the final layer of an already casual outfit. This means it complements the layers underneath it. The pants you wear with the jacket are just as important as the jacket itself. Here are the three best options for pants when styling a denim jacket.  

  • Jeans: Don’t be afraid to pair denim together. While it’s easy to go too far (think Justin Timberlake with Britany Spears at the VMAs), it’s also the most classic look. The number one rule to keep in mind is that contrast is your friend. If you’re wearing a light wash on top, opt for a dark wash on the bottom, and vice versa. 
  • Chinos: Chinos may be the most straightforward option until you get the hang of your denim jacket. A good pair of khaki-colored chinos let the coat do all the talking and is an excellent blank slate for the outfit to grow from. The number one rule is fit. You want to wear an excellent slim fit on the bottom to avoid distracting from the jacket. 
  • Dress pants: In contrast to the ease of chinos, dress pants are the most challenging pants to pair with a denim jacket. The denim jacket dresses down an otherwise more formal or business look in this situation. The best tip to start with is to stick to the darker washes, as they’re the most formal (similar rule with jeans) and won’t look too out of place. Once perfected, this is a trick to help you move from the office to a casual date or drink with friends.
Man in a denim jacket by water reading a book
Image used with permission by copyright holder

What should you not wear with a denim jacket?

The trick to most denim jackets is fit. As you can see from the list above, most pants in your closet will work well with denim jackets if done correctly. Instead of thinking about what you shouldn’t wear with your new denim jacket, you should instead think of how you shouldn’t wear it. In the realm of denim; fit is king. 

Focusing on the jacket’s fit is the start, making sure the shoulder seams hit the curve in the shoulders (think if the seams are extended, make a V-shape below the sternum), the sleeves stop at the wrist, and the body hits the hips. If you live in a warmer climate like Florida or SoCal, try the jacket on over a T-shirt or thin button-up, and in colder climates, try it on over a sweater to ensure this fit.

The rest of the outfit should follow the fit rules as well. The tops should also be the right fit, as something fitting too loosely will look bunched up under the jacket, making it look too small. Something too form-fitting will make it look like you borrowed your father’s jacket. The pants are also crucial to the fit, as baggier fits on the bottom will give you a bottom-heavy look. Think about the look of the genie in Aladdin, massive legs and a tiny chest. No guy wants to look like they have a tiny chest.

The Rock in denim
Image used with permission by copyright holder

How do you style a men’s jean jacket?

Styling your denim jacket is the first thing to think about before purchasing it. If you buy one on a whim but can’t figure out how to wear it, it’ll get lost in the abyss of things you never wear in your closet. It’ll hang next to the sweater your mom got you for Christmas that you only wear when she visits. Therefore, more focused and intentional styling is necessary.

Focus first on the color. Whether you go blue, black, gray, or white depends on the rest of your wardrobe and what complements it the most. We’ll address the different colors and how to style a jean jacket in a minute. Once you select a color, you want to start putting together outfits in your mind; I like to go by season. Assuming you don’t wear one in the summer, think of two to three looks for the other three seasons.

Once you have the color and are ready for the outfit, you need to look at the shirt, pants, shoes, and accessories. Start with two pairs of pants and three shirts, and start mixing and matching. Don’t get overwhelmed because this is supposed to be the fun part. Don’t be afraid to stretch yourself. Sometimes, you’ll put together an outfit, and it just won’t work. That’s OK. That is how we learn by trial and error. An excellent tip for the spring, if you want to add a little flair to your look, is to roll the jacket’s cuffs and add some wrist accessories. Remember to have fun. Now for the colors. 

Shades of blue denim
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How to wear a jean jacket

Blue is the color most people think of when they think of a denim jacket. That’s primarily thanks to James Dean and Steve McQueen. But it isn’t that simple. There are many shades of blue, from bleached (looks like a sky blue color) to raw (the darker blue color), but most of them follow the same rules. Here are some excellent starting points to jump off from with your own wardrobe. 

  • Casual: Jeans are a great pairing if you consider the contrast. Remember to ensure they aren’t the same color and the fit is similar. You can do what is called the Canadian Tuxedo, which is the top and bottoms the same color, but it’s an expert-level move to do it right. There is no more classic look to pair with the denim jacket than the white T-shirt. James Dean made this timeless look a mainstay, but to avoid looking dated, it’s best to update this look with a V-neck T-shirt. Plain white sneakers are the perfect shoes to finish the look, along with brown leathers in the belt and accessories.
  • Dressy: You can dress up this look with fitted chinos, Chelsea boots, and a button-up dress shirt. If you decide you want to dress up the denim, sticking to a darker shade of blue when you buy is the easiest way to simplify your life. 
Zac Efron in black denim
Image used with permission by copyright holder

How to style a black jean jacket

Black denim is less common than blue, making it a fun addition to any wardrobe. Two things to keep in mind with the black denim: It works best in the colder months, and it typically works best with monochromatic (all-black) ensembles. 

  • Casual: A black henley is your best friend under black denim. While it’s a simple shirt, it typically works best as an undergarment and keeps the jacket as the main focus of the look. When paired with black sneakers or Converse shoes, black denim or chinos complement the “blackout” look. Be sure your accessories are also black, as most of the time, you don’t want to pair black looks with brown leather. 
  • Dressy: Swapping out each piece with an upgraded garment takes this look from a casual day in the city to a first date. Swap out the henley for a black turtleneck, the chinos with fitted black dress pants, and the sneakers with leather Chelsea boots or dress shoes.
Man in white denim jacket
Image used with permission by copyright holder

How to style a white jean jacket

White denim is the least common of the colors you’ll see on the street. This means that once you perfect the styling, you’ll be truly unique in your circle. In contrast to black denim in most ways, white denim works best in warmer climates and is upgraded by the presence of colors.

  • Casual: If you like alternative colors in your jeans or chinos (anything outside the standard blue jeans and khaki or black chinos), then this jacket is for you. This jacket also lends itself well to graphic tees, sweatshirts, and hoodies. Simply put, this jacket is a final layer on an outfit that speaks for itself — the most expressive of jackets. 
  • Dressy: Similar to the casual look, this is best for dress pants and sweaters with patterns or colors. Consider this jacket if you have different shades of dress shoes or Chelsea boots, as well. Once you’re ready to have fun and express yourself with the jacket, this is the one to get.

Now that you have a jumping-off point for the denim jacket, you are fully prepared to start shopping for something that can take your wardrobe into the upper echelons of menswear. Embrace your rebellious American spirit or your individuality by channeling your inner James Dean, Steve McQueen, or Bruce Springsteen. Is it time to start shopping for a motorcycle now??? 

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Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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