5 Leather Jacket Outfits (Classic & Modern Men’s Style) | Gentleman’s Gazette

Contrary to what some people assume, the leather jacket has a place in the classic menswear canon, but you have to pick the style and material that’s right for you. Because a quality leather jacket can be a substantial investment, we’re making this guide to help you make the right choice. We’ll provide insight on how to get the most out of your leather jacket by showing off some outfits that really anyone can pull off.

Leather Jacket History

Leather jackets might be associated with stylish bad boys, but their origins are actually classically utilitarian. In the late 19th and 20th centuries, leather jackets were essentially practical garments. Motorcycle jackets actually began as safety equipment as they would protect the rider from road rash in the event of crashes, and provide insulation and warmth while riding.

Leather jackets were also favored by early motorists as they drove through the countryside at the ludicrous speed of 15 miles an hour. These garments would protect their clothes and kept them looking good.

Motorists doing tricks while riding a motorcycle
Motorcycle jackets began as safety equipment, protecting the rider from road rash and providing insulation.

Aviators wore them for vital insulation at a time when airplanes either had open cockpits or lacked climate control. In fact, the famous bomber jacket got its start on the crew decks of bomber planes. For this reason, prior to World War II, leather jackets were rarely worn in social settings, but that changed after the war.

Leather jackets became a popular garment among young men and they were seen as distinctly casual. While some modern men wear a leather jacket to formal events, you really want to keep this jacket as a casual style, which is why it’s featured so prominently in our overall rundown of casual jackets.

Leather jackets were seen as a sign of teenage rebellion in the 1950s, as evidenced by the Marlon Brando film, "The Wild One." [Image Credit: Columbia Pictures/Sony]
Leather jackets were seen as a sign of teenage rebellion in the 1950s, as evidenced by the Marlon Brando film, “The Wild One.” [Image Credit: Columbia Pictures/Sony]

Leather jackets as a whole have had a considerable impact on our popular culture. On the one hand, young men who grew up in the 1940s and after associated the leather jacket with the brave airmen who fought in the skies of World War II, and, conversely, leather jackets were seen as sort of a sign of teenage rebellion in the 50s, especially motorcycle jackets worn by Marlon Brando.

Off the silver screen, in real life, young people copied Brando’s wardrobe and made the Schott Perfecto a household name. But, did you know that some people actually don’t believe that Brando wore the Schott Perfecto in The Wild One? We elaborate on that in our Is It Worth It? review of the Schott Perfecto.

Ryan Reynolds speaking at the 2015 San Diego Comic Con International, for "Deadpool." [Image Credit: Gage Skidmore, Wikimedia Commons]
Ryan Reynolds speaking at the 2015 San Diego Comic Con International, for “Deadpool.” [Image Credit: Gage Skidmore, Wikimedia Commons]

Nowadays, leather jackets remain associated with dynamic and stylish men, such as Dwayne “The Rock” Johnson, Ryan Reynolds, and Donald Glover, or the roles they play on film, like The Place Beyond The Pines starring Ryan Gosling or Daniel Craig in Casino Royale, with other prominent appearances like Ralph Fiennes’ flight jacket in The King’s Men, Brad Pitt’s iconic red leather jacket in Fight Club, and Tom Hardy’s famous Bane jacket in The Dark Knight Rises. 

So, it’s clear that Hollywood has found a lot to love about leather jackets and so can you. What makes the leather jacket appealing is the combination of styles, features, and quality that can be mixed and matched to your preferences.

Picking the Right Leather Jacket

With a myriad of examples from celebrities, it can seem difficult to pick out the right leather jacket, but we’ve narrowed it down for you.

1. Leather Quality

First, you can separate most of the wheat from the chaff by focusing on good leather quality. This tends to remove a considerable of poor-quality or novelty jackets from your choices and if you need help identifying quality, feel free to pursue a lot of our guide on good leather quality, as well as our reviews of the Schott Perfecto and the Belstaff Trialmaster.

Raphael wearing a Belmaster Trialmaster jacket.
Buying the right leather jacket will give you a great cost-per-wear return.

Quality leather jackets will be considerably more expensive, but if you buy the right one, it’ll give you a great cost-per-wear return.

2. Color

Color is another initial consideration to keep you grounded. For a classic leather jacket, you really want to start off with black and shades of brown and tan. Blue, red, and green can be interesting expansion colors, and white, orange, and other colors can be really interesting, but you’re really getting outside of the realm of classic men’s style.

3. Features Relevant To You

Because leather jackets began as practical garments, different styles will have different features dependent upon their intended use. And while we don’t have time to cover all the features of different leather jackets, it’s probably best to pick out features that have to do with you and your personal circumstances.

A gentleman wearing a B-3 Sheepskin Leather Bomber Jacket from Schott NYC, a leather jacket with an insulating lining
A gentleman wearing a B-3 Sheepskin Leather Bomber Jacket from Schott NYC, a leather jacket with an insulating lining

Do you live in a colder climate? Then consider a naturally insulating lining like wool or fur or shearling to keep your body warm. But, if you live in a warmer climate, I would opt to not do the shearling just to live out your fantasies of flying a B-52. You won’t feel or look very cool if you’re all sweaty with all that superfluous insulation.

If you prefer more functional jackets, make sure to pick a pocket configuration that fits your needs. For instance, if you’re left-handed, some of the pocket layouts on a motorcycle jacket favor a right-handed dominant person, so that might not work for you.

An upclose look of a black leather jacket
The minimal the details of your leather jacket are, the more classic it is.

Of course, hardware detailing can be a purely aesthetic choice, so go with what you like but, keep in mind, keep it minimal and it’ll be classic.

4. Jacket Style

Most jacket features will be dictated by the jacket’s overall style. In the classic style, there are really two types of jackets.

First, the more vintage – this has a looser fit, more bulky cut, but it has a lot more hardware on it with styles like the Schott Perfecto and the Belstaff Trialmaster, and second, the more modern jacket, which has a tighter cut and sleeker appearance.

To avoid looking dated, we recommend staying away from styles that are associated with certain eras. For instance, leather jackets that are cut like a blazer can be really reminiscent of styles from the 70s and 80s. While excessive quilting and detailing should really be left in the club scenes of the late 90s and early 2000s.

Finally, it also needs to be said that we’re not going to cover full-length leather coats, like a full-leather trench coat, or dusters

A leather jacket cut and styled like a blazer
A leather jacket cut and styled like a blazer.

5. Fit

You might find advice online encouraging men of specific body types to avoid certain styles of jackets. For example, they might recommend that shorter men wear a more vintage jacket in order to look bigger. But, in our opinion, that advice is really broad and not generally useful. What’s more important is finding a jacket that fits really well for your body type

For many gentlemen, leather jackets represent the ideal of masculine suavity. So, it’s really important to feel cool and confident in whatever you pick.

Find a jacket that fits your body type best.
Find a jacket that fits your body type best.

For instance, for me personally, I don’t like leather jackets that have a whole lot of detail and stuff going on. The Belstaff Trialmaster and Schott Perfecto, while classic, have details like belts and hooks on them that personally don’t do it for me. There’s nothing intrinsic about my physique or my personal style. It’s just something that I learned and discovered by trial and error with time.

So, don’t be afraid to experiment with different styles of other jackets to figure out which one works best for you. But, to help you get started, some styling suggestions coming right up.

Leather Jacket Outfits

We start off with looks good for everyday wear in most climates, as well as cover more seasonal outfits.

Outfit #1: Casual Streetwear

So, this first look is a very modern outfit that most guys can pull off. I’ll start off with brown leather jackets, which are both in suede. One of them is a moto jacket. The other one has these sort of pockets on the side. Both are really good because the suede keeps them nice and casual.

Nathan wearing a casual streetwear look.
Nathan wearing a casual streetwear look.

With the rest of the outfit, we want to compliment the minimal appearances of these jackets, so we’ll add in light T-shirts, whether it’s gray or white, maybe a Henley, jeans are great, whether light blue or dark blue, and sneakers of your preference. I prefer a pair of minimal white trainers, whereas Chris might like Jordans or Air Force 1’s.

The lighter colors keep the outfit airy and casual, but the clean front of the shirt and the simplicity of the jeans don’t jar with the minimalist jacket. And if desired, you can darken this color palette, maybe with a darker T-shirt, a dark polo, or a dark pair of boots in order to formalize the look.

Outfit #2: Everyday Elegance

For another everyday look, albeit a more formal one, I’ll style a brown leather Belstaff Trialmaster. With its attached belt, prominent patch pockets, and exposed stitching, this jacket is the opposite of the minimalist moto. So, I’ll take a different approach.

Nathan wearing a brown leather Belstaff Trialmaster
This look is a bit more formal and more unique in keeping with the bolder appearance of the Trialmaster. Shadow Stripe Ribbed Socks Dark Brown and Beige Fil d’Ecosse Cotton from Fort Belvedere

Let’s add in a light blue OCBD to create color visual interest if the jacket’s worn open or at the neck if the jacket is worn closed. Because the blue shirt contrasts with the brown of the jacket, let’s pair a complimentary tan chino to keep the look tied together. And finish it off with a pair of brown suede chukka boots and our Fort Belvedere shadow-stripe socks

This look is a bit more formal and more unique in keeping with the bolder appearance of the Trialmaster. For a more casual look, consider adding more color like olive trousers or a patterned shirt.

Outfit #3: Insulated Urbanity

Next up are some cold-weather looks. After all, we are working with jackets. So, returning to the suede moto jacket, I’m going to emphasize a really soft silhouette without sacrificing warmth.

Chris wearing an insulated urbanity look.
Chris wearing an insulated urbanity look which is best worn during colder seasons/weather.

Directly under the jacket, Chris is wearing a cotton-cashmere, hooded sweatshirt. The plush texture adds visual interest without being distracting, and the unexpected layering effect, especially when the jacket is open, make it look more memorable. And, of course, the hooded sweatshirt will keep Chris warm with layers, which can be added and removed as needed.

For warmth and style, Chris has on dark wash jeans, which set off the colors on the top half of the body nicely, and he finishes it off with a pair of boots. They illustrate the practical considerations of this outfit, but still look great.

Outfit #4: Accessorized Warmth

For this next look, I’m going to tackle those days when it’s really cold outside. You’ll soon see why I’m opting for the Trialmaster and all of its pocket space for holding accessories. I’ll start off with a dark turtleneck under the Trialmaster, which I’m closing three-quarters of the way up.

The turtleneck creates visual interest at the neck and helps trap my body heat. I’ve gone with a thinner turtleneck fabric to avoid appearing too bulky. This one’s in cashmere. I also have to contend with the Minnesota winters, so let’s add some redundant warmth with a quality scarf. It’s always wise to invest in menswear articles that keep you warm, so I’m opting for a scarf from Fort Belvedere.

Accessories are ideal for adding warmth, so I’ll add another. A pair of denim blue lamb Nappa leather gloves. And Raphael goes into more detail about the utility of leather gloves in cold weather as part of our Men’s Gloves Definitive Guide.

If you’ve ever stood in the freezing cold and felt like your fingers were going to fall off, then I don’t really need to tell you anymore. You know what I mean. While walking or waiting for a ride, it’s great to be able to use your phone with gloves. So, I appreciate that Fort Belvedere offers a line of gloves that work with touchscreen devices.

Fort Belvedere offers gloves that work with touchscreen devices. This is the Denim Blue Lamb Nappa Touchscreen Gloves with Periwinkle Contrast by Fort Belvedere.
Fort Belvedere offers gloves that work with touchscreen devices. This is the Denim Blue Lamb Nappa Touchscreen Gloves with Periwinkle Contrast by Fort Belvedere.

In this look, I opted to match the scarf and the gloves, and you can learn more about pairing gloves and scarves in another post.

How to Pair Overcoats with Gloves
and Scarves – Gentlemen’s Winter Outfit Ideas

To ground this look, I’ll finish off with warm, wool trousers and charcoal and a pair of dark brown boots to tie the look together, and their more muted appearance will give a greater pop to the scarf and the gloves. 

Outfit #5: Moto Cool

When warm weather comes, you don’t have to put your leather jacket away. Here’s a look to help you keep looking and feeling cool in your leather jacket. Because it’s a bit bulkier, we need to be careful with leather jackets in the summer. So, to that end, I’m starting off with a white pique polo shirt for maximum breathability and I’ll be sure to keep my leather jacket open to catch every breeze.

Nathan wearing an outfit that is best suited for warmer weather.
Nathan wearing an outfit that is best suited for warmer weather.

You might be tempted to try on shorts to stay extra cool, but the bulk of a leather jacket will make you look top-heavy. So, instead, let’s go with a light brown or tan pair of cotton trousers and finish it off with a fresh pair of white sneakers. These bright and neutral colors contrast with the richer brown of the leather jacket and help the entire outfit sparkle while staying light enough to beat the heat. 

If I lived in a really hot and humid climate, like Florida, I would be tempted to ditch the leather jacket right away. But, here in Minnesota, where we have transitional seasons, I can keep wearing it and wear it in layers to help me go through the seasons. 


We hope that today’s guide provided you with a lot of inspiration on how to wear a leather jacket. All these leather jackets and leather jackets talk kind of has me wishing I owned a motorcycle.

Which of the outfits did you like best, which one did you not like, what do you want to wear? Let us know in the comments!

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