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A Detailed Guide to Denim Jackets

11 min

Here is a comprehensive guide to one of the most stylish jackets any man can own.



The classic denim jacket is an essential casual outerwear piece for any man's wardrobe. This simple garment has stood the test of time and will never go out of style. Given its strong presence in the world of fashion and personal style, it should come as no surprise that this piece offers the wearer countless outfit options.

To demonstrate this further, I will showcase five outfit ideas for various dress codes using the same Levi's trucker jacket in a classic blue colorway at the end of this guide.


Denim jackets don't get any more classic than the Levi's Type III trucker. If you care about the history, all you need to know is that this jacket's origins date back to about 1905 when Levi Strauss released a workwear denim jacket (production code 506) to accompany his famed pair of work pants.

Following the jacket's inception, six variations of the Type I denim jacket from Levi's would be produced over about forty years. Those workwear roots would stand the test of time, and in 1936, the classic red tab would debut in its original "big E" form, eventually leading to the Type II in 1953.

This marked a boost in the jacket's overall popularity; worn by the likes of Elvis Presley and Martin Sheen in his cult classic film Badlands, rock and roll enthusiasts and many additional pop-culture followers very quickly adopted the jacket. This iteration would last less than a decade before revision to the Type III.

This leads us to what has often become synonymous with most denim trucker jackets today. The fair price point also makes a classic Type III denim jacket from Levi's so great. You can get one of these in various fits, sizes, and colorways for under $100. Considering how durable the piece is and the cost per wear, I think it is an excellent buy for the price.


Nowadays, denim jackets come in many colors, from white to black, deep indigo to acid blue, green to brown, etc. The options are virtually limitless.

When most people think of a classic denim jacket, they think of a medium or deep-wash blue Levi's jean jacket. I will showcase this type of jacket throughout this post, as I think it is the most classic variation of this iconic menswear piece.


In most cases, a tried and true jean jacket will include the following characteristics:


Denim jackets are available in various sizes, ranging from big and tall to as large as 6XL, making it easy to find the perfect fit. I prefer a more traditional style when wearing denim jackets. However, if you prefer a boxier, oversized look, you can follow the advice I'm about to give you and try sizing up. Just remember that we are all built differently at the end of the day.

For the classic fit of denim jackets in a trucker style, you want to ensure that the length remains cropped. This means that the jacket should not fall lower than your hips and certainly shouldn't completely cover your butt. When the buttons are fastened up the front of your torso, the jacket should fit a little snug (not tight).

The jacket's shoulder seam should rest just past your shoulder bone (no more than three-fourths of an inch). This ensures sufficient room for any additional layers of fabric you wish to add under the jacket and prevents it from being too tight. The sleeves should fall right at your wristbone and never be too long.

Again, these jackets should be fitted, but if you want to layer your denim jacket with thicker sweaters or numerous shirts, you might need to size up if you are between sizes (so buyer beware).


Numerous types of denim "washes" exist. Washed denim refers to denim fabrics that undergo a "washing" process to modify their texture and color. This process involves chemicals, stones, and other natural agents that can work together to soften materials in the denim fabric, install patterns, and lighten colors.

Various washes exist, such as "acid" washing, where bleach is introduced to create a lighter and subtly contrasted aesthetic. Stonewash involves the addition of pumice stones, which add a faded look and a softer feel to the denim. Vintage wash employs various methods that cause the denim to look faded and worn.

These are just a few examples of the different types of washing processes. Given the advancement in technology and the refining of washing methods, nearly limitless colors, shades, and patterns can be created for denim.


Suppose you're wondering where the term "Canadian tuxedo" comes from. Legend has it that the term was first coined in 1951 when, after a long day of hunting, American singer and actor Bing Crosby checked in at the Vancouver Hotel but was denied entry due to his double denim attire (denim upper garments of the same color, shade, and material as the bottom trousers).

Crosby's attire was said to have been too relaxed for the elevated ambiance of the hotel. One of the bellhops supposedly recognized that Crosby wasn't an ordinary guest and let him in. Levi's soon caught wind of this event and decided to lean into it by fashioning a custom denim tuxedo jacket for Crosby.

The outfit included a red corsage, a pair of their signature 501 jean trousers, and an interior patch that read "Notice to All Hotel Men." As you can imagine, the name stuck (hilariously so).


Don't be afraid to rock a denim-on-denim look. There are many stylish ways to pull off an all-denim outfit without appearing comical in a "Canadian tuxedo." Before we get into it, I'd like to point out that this guide section is about pairing a classic jean jacket with denim jean pants (not denim shorts). I typically don't wear shorts with this type of outerwear piece, but I do not oppose doing so. I bring this up because I don't have any photos of me wearing denim shorts with jean jackets.

The good news is that everything I'm sharing in this post also applies to shorts (you'll see what I'm talking about as we proceed through the guide).


The most critical aspect of nailing the denim-on-denim look is breaking up the shades of denim. Ensure that the jacket shades with jeans are substantial enough to be noticeable. This is how we can mitigate any "Canadian tuxedo" look.


The best example is a classic denim jacket with a medium wash and dark indigo (or "rinse") jeans for trousers. The darker wash of the jeans is almost black, providing the right amount of contrast.


Black jeans are also almost always a safe bet for the same reason as the previous indigo-wash jeans. Black and blue don't always look great together, but when you have a versatile wash of denim that isn't too light or dark in the shade, it can look very nice, provided you are dressing well for the occasion.

For more advice on how to dress well in general, read this post here.


White jeans pair wonderfully with a classic blue denim jacket. White is a blank canvas that blends well with neutral colors, and shades of blue and green naturally complement white pants (as shown in the above example).

White jeans should be in your wardrobe and can be worn every season. Read my separate post here for more ideas on how to wear white pants throughout the year.


With so many color options available, it can be hard to select just one. Your best bet is always anything in a classic neutral color scheme, such as navy, tan, brown, olive green, etc.

Read my article here to learn why neutral colors are the best for men to wear and pair together.

Leveraging the power of neutral colors can help you get creative. Here's a denim jacket outfit example featuring white jeans, dark olive suede boots, a brown turtleneck sweater, and an earthy-patterned raincoat.

Read this article here to learn why dark olive in suede is the best boot color for men.



This is a textbook example of how to get the most out of your neutral-colored wardrobe staples.

Read here to learn how to build a neutral-colored capsule wardrobe with just fifteen items to craft outfits like this one.

A classic pair of khaki chinos is an easy way to "smarten up" any look. Depending on the weather in your location, this is a great outfit for the spring and fall months, as it provides just enough layering to combat the breeze while remaining light enough for comfort. Swap the white sneakers for brown or olive boots; it's entirely up to you!

See my other article here for over thirty ways to wear khaki chinos.


Here is one of my favorite denim-on-denim looks. It is another stylish example of getting the most out of your neutral-colored capsule wardrobe. I'm wearing a crisp oxford cloth button-down (OCBD) shirt with dark indigo jeans and a classic jean jacket.

Pair it with white sneakers or neutral-colored boots; it's entirely up to you. There are numerous options for a look like this, so long as you remember to break up the shades of denim!

To see more white sneaker outfits, read this article here.


This outfit is a great example of adding fun colors to classic neutral-colored outfits. The crimson chinos go well with the blue denim jacket because of the purple tones in the red. This look is perfect for the fall season, when darker colors complement the cool, crisp air.

Of course, fall means it's time for boots, and adding the sand suede Chelsea boots is a great way to look stylish while still achieving a rugged and sophisticated look. You can also throw on a ballcap for a more casual vibe (Go Braves).

Read my article here to learn more about incorporating color into your outfits.


This next outfit is more of a "proof of concept." When people think of a denim jacket, they aren't expecting a dress shirt and tie. I recognize this pairing is tricky, but it can be done if you pay close attention to the details!

I have a striped blue and white dress shirt, a knit tie, charcoal flannel trousers, and chocolate loafers. If you opt for a tie, it is critical to select one with an apparent texture. The tie and denim jacket should not contrast too starkly when worn together (i.e., shiny necktie and textured denim jacket).

A stark contrast can be very distracting and draw unnecessary attention to one or two pieces of an outfit. I think this can backfire and disrupt the harmony that any good outfit ought to retain. If I opted for a shinier silk tie, it would directly clash with the rugged texture of the denim jacket.

To learn about the best five ties I recommend for men, read this article here.

You can avoid this disruption by complementing textures and patterns. For example, I have a very coarse silk knit tie in a relatively bold striped pattern. The tie's chunkiness looks right at home with the denim jacket. When pairing patterns together, such as the stripes in the dress shirt and the tie, always remember to break up the scales of each to create some distinction between the two.

If I wore a tie with an equally scaled set of stripes, it would look too "busy" to the viewer, with no apparent definition, which could also backfire.

Read this article here for my complete guide to tie clips and bars.

It's never easy to tastefully stick the landing with a look like this, but as you can see, it is very much possible.


A classic turtleneck is an essential item for any man. Here, I have a black one that I pair with black chinos and a charcoal knit beanie. This look is simple, but I want to highlight the boots. They are Chelsea boots in honey-duke suede, rich in color and elegantly textured.

Suede and denim are an elite combination. Trust me, this is a clean and straightforward look that any woman would love to see you in for a nice date in town.

Read my other article here for more fall and winter date night outfit ideas.


If you're trying to decide whether you can wear this classic jacket, stop doubting! Always consider the fit and ensure you pick an easily interchangeable option by paying attention to the style, silhouette, and color.

From ultra-casual street style to elevated dapper to wearing the denim jacket as a blazer with an edge, these are just a few examples of the treasure trove this jacket can be. Unlike other masculine pieces, such as the leather jacket, this is almost always a fraction of the price and is routinely listed as a sale item.

Pick one up if you haven't already, and always remember to stay stylish and blessed!

"The Lord is merciful and gracious, slow to anger and abounding in steadfast love." - Psalm 103:8



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