The classic denim jacket is the ultimate casual outerwear piece for any man's wardrobe. This seemingly simple garment has stood the test of time and will never cease to go out of style (trust me). Given its pedigree in fashion and personal style, it should come as no surprise that this piece affords the wearer virtually limitless outfit options. To prove this point further, I will showcase eleven outfit ideas across various dress codes utilizing the same Levi's trucker jacket in a classic blue colorway.
A QUICK HISTORY
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.
OUTFIT #1: CLASSIC STREET STYLE
This first outfit is simple enough. Black t-shirt, black jeans, white sneakers, and a ballcap to lean more into the casual nature of this fit. Simple, comfortable, and effective. This combination presents a very clean and low-contrasting silhouette, which can be effective for slimmer or fitter men. For those who are heavier-set, the darker palette of this outfit can do a lot to present a slimmer aesthetic, but of course, committing to an adequate diet and nutrition routine is always the best way to look dapper for every occasion, full stop.
OUTFIT #2: STREET REBEL
Like the previous example, simple can often be the most effective way to go for a denim jacket. An old-fashioned gray hoodie with dark-wash jeans can look sharp atop a sleek pair of minimal white sneakers. This is a tremendous minimal street-style uniform that's as comfortable as it is classic.
This is a denim-on-denim ensemble, but I'll explain how you can best pull this look off in the next outfit.
OUTFIT #3: SMART CASUAL DENIM-ON-DENIM
I know what you're thinking, "denim-on-denim?" Yes, it can be taboo, but I will tell you a little secret... What gives the denim-on-denim combination a "bad wrap" is when the washes (a.k.a. shades) of denim match the top and bottom pieces. Breaking these up by adding more contrast will prevent you from looking silly, guaranteed.
This 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!
OUTFIT #4: CLASSIC NEUTRAL
Let's take that same ensemble from the previous outfit and swap out the dark denim pants for classic khaki chinos. This is a textbook example of how to quickly change the entire look and feel of an outfit with just one garment change. The lighter-colored chinos are decidedly less casual and are thus a great way to "smarten up" the look.
If you need to add a sweater underneath for warmth, go right ahead! Speaking of which...
OUTFIT #5: LAYERED SMART CASUAL
Layering outfits is a great way to provide warmth to the wearer and add sophistication to any outfit. Here, I have thrown on a gray crewneck sweater to the previous outfit to achieve a more smart-casual vibe. Keep the neutral-colored boots, or wear some clean white sneakers; the choice is yours! Classic, timeless, and dapper.
A quick note about layering: two layers is often fine, four is generally too much (depending on what you're wearing), but three layers are perfect. A great way to nail your layered looks every time is to ensure that each layer becomes thicker as you work your way out; that's to say that whatever your outer-most layer is ought to be the thickest garment, the mid-layer second thickest, and inner-most layer the thinnest. Each layer should look good on its own, so if you must subtract layers (i.e., removing your jacket if you enter an area where it is no longer needed), then ensure to bear this in mind.
Stick to those guidelines, and you can rarely go wrong!
OUTFIT #6: AUTUMN VIBES
This look is an excellent example of incorporating fun colors into neutral-colored outfits. Here, the crimson chinos work well with the blue in the denim jacket because of the hues of purple found within the red. I think a look like this is great for the fall season when darker colors compliment the crisp, cool air often commensurate with the changing of the season (depending on where you live that is). Of course, fall means boots, and including the sand suede Chelsea's is a great way to remain dapper while still wanting to be both rugged and sophisticated. Throw on a ballcap to lean further in a more casual direction (Go Braves).
OUTFIT #7: SWEATER WEATHER
I think that a chunky cable-knit sweater looks excellent because of its texture. You'd be hard-pressed to find a woman who didn't like a strapping man in one of these. Taking the texture of this kind of sweater and pairing it with the rugged sophistication of a classic denim jacket can be an incredibly effective way to stand out and remain warm. The cream-colored sweater looks exceedingly handsome atop a navy blue pair of chinos. I finished this look with a pair of leather coffee sneakers, which I think harmonize well with the lighter brown hues in the sweater.
OUTFIT #8: FALL & WINTER DATE NIGHT
A classic turtleneck is simply a must-have for any man. Here, I have a black one paired with black chinos and a charcoal knit beanie. This look is simple overall, but I'd like to draw special attention to the boots. These Chelsea's in a honey-duke suede are both rich and elegantly textured. Trust me, this is a clean and straightforward look that any woman would love to see you in for a nice date on the town.
OUTFIT #9: RUGGED BLAZER
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, selecting one with an apparent texture is critical. 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.
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.
It's never easy to tastefully stick the landing with a look like this, but as you can see, it is very much possible.
OUTFIT #10: NEUTRAL RAINMAN
Of course, we have to cover our bases by adding an option for the rain. In fact, this could be its own article (how to style a denim jacket in the rain), but for now, this example is a great way to showcase the garment's versatility in a single outfit.
I have chosen a patterned brown Mac Jacket (a.k.a. raincoat), a beige turtleneck sweater, white jeans, and dark olive suede boots. The denim jacket is an excellent mid-layer to this look and adds a bit of ruggedness to an otherwise clean ensemble. Of course, the dark olive suede boots go with just about anything, and I think they are a great way to pair smartly with the boldness of the white denim jeans.
OUTFIT #11: COZY COATED
Continuing to cover our bases, here is the final look, which includes a camel overcoat (great for winter). One of the drawbacks to this type of denim jacket is that it doesn't afford a lot of warmth during the peak winter months when it can be frigid (especially if it snows in your region). Luckily, what the denim jacket lacks in warmth, it more than makes up for in versatility. Again, relying on a neutral-colored palette, this ensemble is another testament to the power of color. Green and blue are analogous colors and look great when paired with the camel overcoat. Timeless, simple, and effective.
DON'T SLEEP ON THE CLASSICS
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.
