There are some men who can pull off leather jackets effortlessly – thrown carelessly over a white tee and paired with black aviators and holding a cigarette for extra swagger. James Dean nailed that look in Rebel Without a Cause (1955). John Travolta sensationalised the too-cool-for-school style with his coiffed hair in Grease, a movie released in 1978 and even after 40 years, is referenced as the catalyst the bad boy look that is still all the rage today. 

Marlon Brando wearing the iconic black Schott Perfecto leather jacket in the 1953 movie, The Wild One. (Credit: Rex Features/Everett Collection)

Worn as flight jackets in the early 1900s, black leather jackets first shot to fame in 1953 when Marlon Brando donned a black Schott Perfecto in the now-cult film The Wild One. It then became the uniform of hedonism for 1970s punk bands and soon associated with rebels and bad boys.

Brushing off all nuances of style leather jackets have been through, it is one of the most timeless (and toughest) items you can own in your wardrobe. It is an object of desire — a purist symbol of rebellion and freedom, transcending time, subcultures and history.

In fact, history and celebrities have played a pivotal role in ensuring that the leather jacket has remained a menswear staple. If you look at the most stylish men of our era, they all have been photographed in a biker jacket at the peak of their career. The likes of Steve McQueen, Johnny Depp, Brad Pitt, Justin Timberlake and Chris Evans would instantly come to mind. The hottest Hollywood stars like Robert Pattison, Ryan Gosling, Drake and Idris Elba have all been snapped in leather too.

Robert Pattison photographed in a leather jacket ensemble. (Credit: Esquire UK)

How you wear the leather jacket is almost as important as the jacket itself. It has to be dressed up – each time you put on a leather jacket, you up your game in fashion.

Think crisp cotton shirt – white to be safe but coloured ones are great to switch things up a little. Pair it with a sweatshirt or a turtleneck for a more dapper look. Complete the refreshed bad boy look with a pair of pressed formal trousers in black, and white sneakers. Black leather boots give a more rugged feel. Don’t go down the stonewashed jeans, plaid shirts and t-shirt route – that’s a bit of a mid-life crisis dad vibe.

The good news? You have years to perfect the leather jacket style – bomber, biker, racing, you name it — because this classic look is not going anywhere. Here are three easy ways to style a black leather jacket without having to try too hard.

Keep it Classic

Keep it simple but unpretentious when putting together a full leather jacket look. (Credit: George Elder)

You can never go wrong with a well-fitted leather jacket. It should feel slightly heavy and sit comfortably when worn over a t-shirt. Choose a piece that is slightly oversized so that you can breathe but it should still hug your body nicely. Too many creases mean it’s too tight for you. Invest in brands like Givenchy or Saint Laurent for a timeless statement piece. Look into the finer details such as asymmetrical fastenings and the diagonal zips to block out the wind, pockets for utility, inner linings for comfort, and the quality of its material.

Less is More

Dave Franco puts on a dapper look with the leather jacket. (Credit: Getty Images)

If you are able to maintain a ‘less is more’ ethos when dressing up, that’s great. Achieve a more formal and spiffy look with a leather jacket by swapping black jeans for pleated wool trousers; boots for patent leather derbies and a casual t-shirt for a crisp white dress shirt with all the buttons done up. It’s the same method, and probably the same jacket; you’re just upgrading the pieces around it. Never, ever attempt a tie with one – they don’t go well together.

Add Layer, Break it Up

Japanese footballer Hidetoshi Nakata in a layered leather ensemble. (Credit: Trunk Archive)

Going all out by pairing a black biker with slim black jeans can sometimes look very flat. Dressing in just one colour can look rather boring. Break things up with coloured pants and a few extra layers. Perhaps a gilet under a simple, roomy bomber would do the trick; or a hoodie for a more casual look and a nice wool scarf to ramp up the sophisticated look (only if the weather permits). If you’re really up for an all-black look, put on a white shirt inside for an extra dimension.

Martin Teo
Deputy Editor
Martin loves traveling the world to see ancient ruins and classical architecture. He enjoys the culinary experience of various cities but (still) refuses to eat anything insect-like. On a daily basis, he finds time hitting the gym to compensate for the amount of food he needs to eat just to write an article.