I Have Discovered the Ideal Number of Leather Jackets Every Man Must Own
This is One Thing, a column with tips on how to live.
A friend once told me that purchasing your first leather jacket is just as important as losing your virginity. In that sense, my cherry popped in the summer of 2019. The scene of the crime was a Los Angeles vintage shop, draped with the long shadows of a late-afternoon smolder. I usually play it safe in these venues, opting mostly for the slightly more luxurious versions of the stuff I already wear—business-casual button-ups, tropical short-sleeves, reclaimed Levi 511s. But for whatever reason, my girlfriend and I found ourselves leafing through the outerwear hangers, which—like nearly all the clothing stores on Sunset Boulevard—were absolutely dominated by thick shawls of black leather.
Before long, I was holding one of the boutique numbers by the scruff of its collar. The jacket was forged in the Joey Ramone tradition: studded with gleaming zippers and buttons, two enormous lapels crisscrossing down the shoulders. It was, in other words, cool. Even so, it was subtle, at least enough to avoid accusations of garish, Bret Michaels–like excess. It was not a costume, but it was still a statement. My wardrobe was not known for its statements, which is exactly how I made it to 28 without owning a leather jacket.
My girlfriend, ever the supportive partner, told me that perhaps my fashion sense could use an update. Maybe, deep down, I was the type of guy who could wear a leather jacket with authority and impunity. Maybe, sometimes, it was OK to look hot. With her endorsement, I took the jacket to the counter and left the store a changed man.
The jacket has gotten a decent amount of wear in the years since. I would not say the acquisition has been as life-altering as, say, the introduction to the infinite possibilities of human sexuality, but I do sort of understand where my friend was coming from. Wearing a cool leather jacket—with copious bits of iridescent metal gleaming in the darkness—is a bit like cosplay. You become something larger than yourself.
Still, I belong to none of the societal sects that treat black leather as a fundamental part of their daily uniform. I am not a biker, nor have I ever been relinquished from The Matrix by Trinity and Morpheus. Therefore, my jacket is reserved primarily for social functions that possess an air of millennial chicness; concert tours, birthdays of hip friends, rooftop parties of questionable legal solvency—all destinations where I’d prefer to attend as anyone but myself. There is simply so much power in letting a leather jacket do all the talking, and frankly, that knowledge needs to be in the core curriculum of every public school.
But there’s a crucial caveat here, and it’s something you really only learn after becoming a leather jacket veteran. For any of the more mundane (and much more common) ceremonies of life—like, I don’t know, running to the store to buy a can of tomato paste—I quickly realized that the cool leather jacket can occasionally have the polar opposite effect on your victorious aplomb, which is to say: You can begin to feel really fucking dumb while cutting a Ramones silhouette in a room of T-shirts and jeans. In its worst applications, a cool leather jacket can leave you looking like a tragicomic clown—trust me, I’ve been there. I have listened to my buckles and straps clink against each other in the fluorescent void of the dairy aisle. I’ve been the single most overdressed person on the C train. I’ve sweated like a pig in a basement den.
This is the key to my overarching theory of all leather jackets, which is that every man needs two of them: one that is cool, another that is normal.
By normal leather jacket, I am of course speaking of the generic types worn by Ross from Friends, Jon Stewart during his MTV era, and, probably, your mom. The normal leather jacket usually is entirely black or brown, includes exactly one straightforward chest-to-belly-button zipper, and is devoid of any punk-rock flourishes (no buckles or studs, and certainly no spikes). It’s stock image–like, neutral, and featureless. The normal leather jacket calls no attention to itself, and therefore can be easily deployed in any social circumstance—a performance-first stand-in for a hoodie, or a cardigan, or any other piece of warm outerwear. It’s identifiable as a leather jacket because of the material it is made of, rather than any imposing, angular verve in its shape or design. Wrap it around your shoulders and you’ll quietly fade into the background, while maintaining the personal satisfaction that you are—in fact—wearing a leather jacket in the middle of Walgreens. What could be more naughty?
A cool leather jacket, on the other hand, is the first thing anyone notices about you when you walk in the door—and there is truly nothing more embarrassing than being fashionable when everyone else is attempting only to be functional. Honestly, you can divide most of life’s pageantry into events that require either a cool or a normal leather jacket, so it’s vital that you give yourself the option between the two.
Of course, Derek Guy—the foremost menswear expert on the internet, and someone who knows a whole lot more about fashion than I do—pushed back on my premise a little bit. To Guy, one must know themself before they know what leather jacket is right for them.
“Some guys aren’t the wine bar type, so they don’t need a very soft, luxurious lambskin leather jacket,” he explained. “Other guys value comfort and sit at a desk all day, so they may not want that heavy horsehide or cowhide jacket that takes forever to break in and is designed to make you look like Marlon Brando from The Wild One. There’s going to be some experimentation. But I would not go through a checklist and think that you need one of each design, like collecting animals for Noah’s Ark. Think about what you want to communicate, what kind of wardrobe you want to build, and how those clothes work for your personality and lifestyle.”
Look, Guy is probably onto something there. If you do the homework and peer deep into your own soul, you’ll likely become a more erudite arbiter of your own fashion sense. But I’m still sticking to my two-jacket policy. No, you probably shouldn’t go around accumulating leather like baseball cards, but the scenario Guy laid out—owning a sumptuous lambskin and an outlaw cowhide—seems like a perfect lifestyle for me. The duality of man!
Still, if your budget (or self-respect) precludes you from owning more than a single leather jacket, I recommend going with a statement piece. There are three days a year when the Ramone form can get you about as close to God as possible, and the investment is worth it for that euphoria alone. But you know what supreme confidence is? Wearing a plain-Jane leather jacket while knowing that you’ve got a ringer waiting in the closet, ready to pounce at any second. Go pop that cherry. You’re missing out.
