Style Debate: Can A Regular Guy Pull Off A Leather Jacket?

It works for rock stars and movie icons. But can it work for you? Two distinctly non-rock or movie star Esquire writers hash it out.

BY Sam Parker and Finlay Renwick | Sep 5, 2016 | Fashion


Most men have a 'leather jacket story'. Unfortunately, they're usually tales of horror rather than romance.

For a brief window in the winter of 2007, I took to wearing a genuine, honest-to-God biker jacket made from worn brown leather, with a fixed mesh lining and vents at the back to keep you cool as your tore down Highway 61.

It didn't matter to me that I didn't have a motorcycle or even—thinking about—a driving license. The jacket tricked me in believing I could be someone else, because for 99 percent of us that's what the leather jacket is: fancy dress. In your mind you transform into James Dean in Rebel—in everyone else's you're Henry Winkler at a Happy Days fan convention.

Like a soft-top sports car, the jacket felt wonderful to slip on and was certainly a thing of beauty in its own right but anyone who saw me in it automatically thought 'tosser'—and they were right. It took a week of piss-taking from my friends—who frankly couldn't believe their luck—before good sense prevailed and, with a vague sense of Bildungsroman, I folded it up and put it in the attic where I hoped one day some distant progeny could discover it and embark on their own leather jacket horror story.

Because let's be honest: there is a sweet spot when men—some men—can pull off a leather jacket, and it's around 22. The problem is that by the time most have plucked up the courage to try it, they're 44.

Nothing—not the sudden earring, not the half-hearted tattoo, not the seedy afternoon at an InterContinental with your PA—nothing screams mid-life crisis like the leather jacket.

Even the young bucks rarely get away with it and that's because a good leather jacket costs money, so they often end up dressed in 'pleather' instead, a material so noxious it warrants a solemn debate the next UN Security Council.

If you do happen to be young enough, slim enough and edgy enough—by which I mean a little bit tough, a little bit arty and more than a little bit charming—to pull off a leather jacket, then congratulations: you've won the style lottery.

Just be sure to enjoy the moment—and more importantly, recognise when it's passed.

- Sam Parker


Leather jackets are a funny one, aren't they? The kind of item that always looks so daring and effortless on famous, handsome men of old, men like James Dean, Marlon Brando and Johnny Depp (before he got fat, sad and covered in eye liner), but the thought of actually wearing one? Probably not.

That was my opinion too, before I found the one.

It was last year and I was in Brighton (no jokes please) wondering aimlessly through the rabbit warren of the lanes where, in a dusty second hand shop that smelled how I imagine the '60s to have smelled, I found the leather jacket that was to completely change my opinion and my life… well not my life, but still.

It was a black leather biker and it was half-battered, with a broken zip and an illegible receipt in the torn inside pocket, but it fit like a dream and straight away I felt two feet taller and 33.5 times cooler, which brings us to the beauty of the leather jacket: it's a Power item of clothing.

A proper biker jacket, like a well-cut suit, is the kind of thing that you can wear like armour. It is both risky, timeless (We'll always remember Brando in his Schott Perfecto… and Danny Zuko, but let's try our best to forget that one) and a challenge, but when worn well looks like the most insouciant thing in the world. It is contradictory and bold and that's why I love it.

In my opinion the leather jacket has a bad rep because too many people overdo it, the jacket is your statement piece, all other aspects of your outfit should fall into step. Black boots, black slim-fit jeans and a monochrome t-shirt and you're done; a clean, cheap and versatile look that you can run with all year.

 I'd be lying, however, if I were to say that I don't feel like a complete pretender in it sometimes.

I am middle class and from the countryside and at times when I'm rolling through east London feeling like a mad punk on my way to some seedy basement club, rather than an exposed brick brunch spot, I catch myself in the reflection of a shop window and my sub-conscious screams "TWAT, TWAT, TWAT, TWAT" at me like an ego-shattering internal machine gun.

But in this current fashion landscape of throwaway quality, blink-and-it's-gone trends and bright, branded and cringe-worthy streetwear, there's something comforting in owning an item that was cool 50 years ago and will remain cool for 50 years more (and more), which the leather jacket inevitably will.

There aren't many pieces of clothing you can say that about, even if I do have to grapple with feeling like an extra from Grease every now and again.

- Finlay Renwick

From: Esquire UK.