Most men look like they’re wearing a costume when they put on a leather jacket. They put it on and suddenly they think they’re Steve McQueen or some brooding extra from a 90s grunge video. It’s painful to watch. The jacket ends up wearing the man, mostly because they’ve overthought the ‘vibe’ and forgot that it’s just a piece of animal skin meant to keep you warm and not die if you fall off a bike.
I’ve spent way too much money trying to get this right. Over the last eight years, I’ve owned six different leather jackets, ranging from a $200 thrift store find to a $1,200 Japanese horsehide monster. I’ve tracked the wear. I even weighed them—my Schott 618 weighs exactly 5.4 pounds, which is basically like wearing a small, angry toddler on your shoulders all day. But after all that, I’ve realized most ‘guides’ tell you to wear things that look ridiculous in real life.
The mistake I made in London
It was 2016. I was in London, feeling fancy, and I walked into the Sandro store on Regent Street. I bought this black, slim-fit biker jacket for $895. It was beautiful. The leather was soft as butter. But I bought it one size too small because the salesperson told me it would ‘stretch to my body.’
That was a lie. A total, expensive lie. Leather stretches a bit, sure, but it doesn’t fundamentally change its molecular structure to accommodate your love of craft beer. I wore it to a dinner that night and I couldn’t even reach for my water glass without feeling like the seams were going to explode. I looked like a stuffed sausage. I spent the whole night sweating and miserable, trying to act ‘cool’ while my circulation was being cut off at the armpits. I ended up selling it on Grailed for half what I paid two months later. Never again.
The biggest lie in menswear is that a leather jacket should fit like a second skin. It should fit like a jacket. If you can’t wear a hoodie under it, it’s too small.
The part about brown leather that people hate
I know people will disagree with me on this, and I might be wrong, but I think brown leather jackets are almost impossible to pull off unless you’re over 50 or literally own a horse. Every time I see a guy in his 20s or 30s wearing a brown cafe racer, he looks like a geography teacher who’s trying to reclaim his youth. Or Indiana Jones. Neither is a good look for a Tuesday at the office.
Black is the only real option. It’s forgiving. It hides the fact that you haven’t cleaned it in three years. What I mean is—actually, let me put it differently: Black leather is a neutral. Brown leather is a statement, and usually, it’s a statement about how much you like the 1940s. Stick to black. It’s just easier.
How to actually wear the thing
If you want the best leather jacket outfits, you have to stop trying to be ‘edgy.’ The best outfits are the ones where the jacket is the most boring thing you’re wearing.
- The Uniform: Plain white tee (heavyweight, like a 280gsm Uniqlo U or a Bronson Mfg one), black selvedge denim, and some beat-up boots. Red Wings are fine, but everyone has them. I prefer something like Truman Boots or even just some old Docs if you don’t mind the break-in period.
- The ‘I Work in General’ Look: A grey hoodie under the jacket. This is the only way to make a double rider (the one with the big lapels) look like a normal piece of clothing and not a costume. It kills the ‘tough guy’ energy just enough to make you look approachable.
- The Risky Move: A black turtleneck. I used to think this was peak pretension. I was completely wrong. If the jacket is rugged enough, the turtleneck makes you look like you actually know what you’re doing.
I refuse to recommend AllSaints, by the way. Everyone loves them because they’re ‘accessible,’ but the leather feels like it was harvested from a very stressed-out hamster. It’s too thin, the hardware is cheap, and they smell like chemicals. If you’re going to spend $500, just wait and save another $300 to buy something that won’t fall apart when you look at it funny. Total waste of money.
A brief tangent on my dad’s jacket
My dad had this old fringe jacket from the 70s. He looked like a budget version of someone from Easy Rider. He wore it until the fringe literally started falling off in the grocery store. It was hideous. But the thing is, he didn’t care. He wore it to fix the lawnmower. He wore it to get the mail. That’s the energy you need. Anyway, I don’t recommend fringe. Unless you’re actually in a commune.
The weight matters more than the brand
I’ve tested this. I wore a 2.5lb ‘fashion’ leather jacket and my 5.4lb Schott through a Chicago November. The fashion jacket was useless. The wind went right through the seams. The Schott felt like armor.
If your jacket doesn’t feel slightly heavy when you pick it up, it’s not going to drape right. Cheap leather is light and crinkly. Good leather has gravity. It should feel like it could protect you from a low-speed slide across asphalt, even if the closest you ever get to a motorcycle is an Uber XL.
I genuinely think people who wear leather jackets with dress shirts look like undercover cops trying to blend in at a rave. It’s a disaster. Just don’t do it. The collar conflict alone is enough to give me a migraine. Keep it simple. Tee, hoodie, or a sweater. That’s it. That’s the whole trick.
I still have that Schott 618. I’ve had it for five years now. It still isn’t fully broken in. The sleeves still have those rigid tunnels where my elbows bend, and it still smells like a tannery. Every time I put it on, I wonder if I’m actually ‘cool’ enough to wear it, or if I’m just another guy in a costume. I honestly don’t know the answer. Maybe that’s the point. Buy a real one, wear it until it’s grey, and try not to look in the mirror too much.
Buy once, cry once.
