I googled “what men’s hats are in style” at 11pm on a Tuesday night like any normal well adjusted human being would and was presented with a carousel full of, a fedora, a bucket hat, a thing called a “gorpcore beanie”, and a flat cap next to a stock photo of a dude just inches away from selling me a horse. None of this is inherently wrong. All of it is still useless if you’re half naked in your hallway wondering what the fuck to throw on before you run out the door. Internet style tends to address the question of “what’s in” as if it’s a boardroom matter. It’s not. It’s you questioning whether or not you look like a fuc*ing idiot wearing that and those are two very different lists.
I stopped scrolling and started looking.
Not at online magazines, at my neighbor on the train, at my barista, at dads at pickup, at myself in store windows feeling mildly defeated by my own reflection. And honestly, once you start looking at what people are actually wearing instead of what websites want you to think they’re wearing, the list becomes a lot shorter and a lot more fascinating than any algorithm will tell you.
The truth about what people are wearing vs what publications want you to
Both the flat cap and the fedora, the two hats every online “mens style guide” will rotate through, have become in practice costume hats. I own a flat cap. Bought it too much gusto in 2019, wore it to four separate occasions before Covid ended that behavior, and every single time someone asked me if I was going somewhere. Somewhere, specific. Like to a wedding or a funeral or god forbid, a heist. There’s your tell right there. If your hat is reaching an ask-about-your-day level of intrigue, it’s not street style, it’s costume, and they are categorically not the same.
What I’ve actually seen worn on normal heads in normal weather, though? A much, much smaller pool. The five panel has made a resurgence, and not the loud logo stitching, rock-bottom price acetate version, I’m talking about the ones that are plain wool or corduroy in a neutral color that doesn’t nod at any surrounding trends. I now own three of these. Three! After firmly committing to only needing one before realizing they hide any existing style sins you may or may not be entertaining. The key is they’re not trying to look like a hat. They just look like… a hat on your head. And once you pull that paradox off nothing else will satisfy you quite the same.
The beanie is having a quiet resurgence as the go-to cold weather hat in mens street style. And not wool textured or overly long sleeved like it’s making up for lost time in the closet. Just your standard beanie that fits snug to your head, stops right above your ears, and doesn’t bunch up in the back like a melted pumpkin mold. I used to roll my eyes at how bland they looked on other people until I tried it for myself and realized I had been wearing my beanie too large in an attempt to look cool. A coworker actually told me not-so-jokingly that I looked like I was wearing a sock on my head. She was technically right. I had been wearing a sock.
Last but not least we have the glorious bucket hat. Boy did I judge that trend. For no other reason than I kept seeing bad festival photos pop up anytime someone talked about bucket hats I was out here convinced they went away. They didn’t! A friend with terrible taste (joking, love you Mara) and one excessively hot sunburnt weekend spoiled me on how great they are and now I have two, likely will not stop buying them, and they’re the only hat I’ve found that can handle actual weather. Rain, shine, a spilled beer onto the brim at a BBQ, they shrug off everything.
The concerning lies about baseball caps
This is where I start to rant because the whole conversation around baseball caps in men’s street style has become problematic at worst and disingenuous at best. Every article tells you you “need a baseball cap”, period. No discussion on shape or fit, no mention of different contexts where a baseball cap can actually work and others where they just scream “mall tourist”. Give me a break. Any fucking blogger can google “baseball caps in men’s style” and paste a stock image of some cap worn too high on some sketchy influencer’s head and call it a day. Tips, guys I want tips.
The baseball cap that I actually wear on my head that doesn’t look like a souvenir is bent and worn down in all the right places. Stuck with me so long the brim has curved exactly how I like it, and the hat itself is faded from my scalp naturally. Doesn’t everyone’s look like that? The ones I tried on before that felt “too stiff” just felt… stupid. Like I put it on and my head looked enormous under the flat brim. But when your cap is molded to you, it looks like you picked it that way. Like you wore that hat every goddamn day until it was yours.
I went through a bad baseball cap phase in my late twenties once. Bought four all within the same month because I was convinced that since I liked the way one looked I just needed to grab different options within that “system” I was sure Nike was selling me. Thing is, I didn’t like any of them. One was too loose at the back, one sat too high on my forehead making my head look like a cantaloupe, and did I mention I still have all of them? Caps are twenty eight dollars.
Throwaway twenty eight dollars. It takes me months to get rid of clothes that aren’t this expensive and the thought of literally throwing out a dumb hat just hurts my soul.
The thing that will work for you looks like whatever you already have and loved wearing so much you wore it until it fits you better than it did the person who made it. Not the logo, not the color options “available in fall 2022”, not whether or not Little Glossy Magazine said they were “rebuilt streetwear” this season. Hoodies aren’t trendy, they just exist, and hats are the exact same way if you wear them long enough for them to get past that manufactured perfection.
If I’m being honest, that means my list of “what to wear” is pretty small right now. A standard five panel in a muted color. A basic black fitted beanie for when it actually gets cold outside, not just “fall-ish” like everyone else thinks it does. A trusty bucket hat I spent far too long mocking, and one baseball cap worn until the brim dropped just how I like it. Until it stopped looking like a hat and started looking like mine.
Marcus started the menswear section after getting fed up with coverage that called a two hundred and fifty pound hoodie an easy Tuesday buy. Based in London, he writes about pricing, returns policies and what brands actually deliver.
