When Levi Strauss created the denim jean in the 1870s, he didn’t wait long to capitalize on the incredible runaway success by creating the top half of the ensemble with the denim jacket 10 years later. As American as biscuits and gravy, the denim jacket became a staple in our nation’s fashion, symbolizing rebellion and individualism.

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 when trying to wear one, below is a guide to help you bring the timeless classic to life in your own wardrobe.

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.  

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.

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, a 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. 

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. 

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. 

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.

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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