The Hat Man Cometh
Hello! I started compiling this post a week or so ago, when I was feeling extremely off about the state of my hair and wished for a litany of interesting hats with which to cover it up. Since then, I’ve shaved it off again—I wish I could have an interesting mullet with braids down the back, but the years-long growing-out phase plummets me every time into a state of gender dysphoria and general feelings of ugliness. Having my flavor of curly hair is all fun and games when it’s long, but when it’s in the two-to-four inches state of growth, it’s hopeless to me unless smothered in the stickiest gel I can find at a drugstore or stuffed shamefully into a cap.
I like having a shaved head, and have about ten times in the past ten years, but the one thing a buzz does not lend itself to is hat wearing. They gape awkwardly above the ears, make my forehead look never-ending, and just don’t jibe with my hairless skull. Something about the fringe peeking out of the brim is so essential to my experience of hat-wearing. It’s one of the few reasons I keep fruitlessly attempting to overcome the growing-out phase, but I’ve given up. If hats aren’t for me, they can be for you. Below is a selection of incredible ones I’ve come across in my travels, plus my thoughts on each. I’m sick right now, so if there are any typos below, just know I’m hopped up on cold medicine. Is it only Benadryl that summons the Hat Man? If I see him, I’ll tell him you say hi.
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Before I shaved my head, I was seriously considering purchasing this beanie—it selling out felt like a sign that it was shaving time. I generally do not like beanies, as they feel so rote and uninspired in their usual shape, but this frayed mohawk design stitched with little x-es is unlike anything I’ve seen before. I hope Hurtence (my favorite milliner) makes more like this for whenever I decide I can dip my toe into the hat pool again or it just gets too cold for me to resist.
As you probably know, I’ve been watching One Piece, and the idea of owning a utilitarian straw hat to accompany me on all my adventures is so appealing. This one is the platonic ideal in shape, brim size, and straw color, and it’s a great price.
This vintage cap reminds me of some of Hurtence’s best designs—I love how it’s sleek but kind of severe, like a shark in dark water.
The antithesis of a beanie. Wearing this with a fur coat would be the epitome of glam winter styling, but I could also see it with a long white dress in the spring, when the cherry blossoms actually bloom.
This Comme cap would look really cool on someone with a pixie cut and thick bangs, probably straight-haired, but I could easily be convinced of other configurations. It would be so easy to throw in a bag or scrunch into a pocket, and is another antidote to the beanie tedium of winter.
This beanie looks like it was drawn by a child, which makes it good. Its colorway can pass as neutral because of its variance, and this would be a great signature hat to have as your go-to all winter long, especially with some sort of dark trench coat or puffer underneath.
This Issey Miyake number frames the face so perfectly and reminds me of the Nicklas Skovgaard cap two images below for cheaper + all the benefits of secondhand shopping.
This velvety hat is so Baby Sitter’s Club to me, I wonder if one like this was ever in a cover illustration because of how strong my association is, but its sunset orange keeps it from feeling too childish.
Incredible either for super short hair or super long hair. Drama in length adds to the drama of the hat.
This kind of looks like a Chasidic man’s cap, but I’ll chalk it up to Yentacore and just say I like it. Perfect for a goth summer.
This cap has the elements of a biker’s hat that I like—jaunty, short-brimmed, sporty—without the usually-heinous colorways or sponsor logos that so often mar them. I like that the snap can be unsnapped, though I don’t see how it could be worn that way, but I’m open to having my mind changed.
This is a very jester-y hat and I think it’d look best on someone with huge, curly hair.
This is a pirate hat. Idk what else to write, it’s insane, I just included it because this is my blog/newsletter and I can.
One of the few hats I’d consider wearing with no hair because the bow functions as kind of an updo in and of itself, much like how J.Kim has experimented with braided nylon “hair hats” in the past few years.
I really think true purple will have a huge moment in culture soon. It was my favorite color as a kid (nonbinary foreshadowing).
Another hat that’d look best with big, curly hair. The mannequin actually does it justice—I love the contrast with the bleach blonde. This shape is so relegated to fur, to see it in feathers is unexpected and cool.
There are a billion vintage sailor hats on Etsy if you don’t have a Vaquera budget, I like that this one is leather and its navy/crimson (lining) colorway is neutral enough for daily wear but not boring in the slightest—even Vaquera didn’t do a navy leather version of their sailor cap, which I think would have been very compelling.
I love the idea of a pillbox cap, though I can’t see myself wearing one, but if I did, I’d avoid the mod, streamlined ones like at Bagtazo and favor something textured and musty-looking like this one. I just think it’s paradoxically more contemporary and less costumey, perhaps because it has some slouch to it.
I love a cloche shape and think this is the PERFECT shape for people with chin-length hair or growing out Fuck Ass Bobs.
Another great, neutral straw hat, but this one shows off your face more and would be cuter with short hair than the one above. The intense texture would work especially well with a straight pixie.
Inspired by traditional Ukranian hat silhouettes, this cap takes things horizontal, which I almost never see knit hats do. Another great candidate for a non-rote winter hat, and this one is truly neutral—it could be the signature hat you wear with every outfit for the rest of winter.
I have a love-hate relationship with bucket hats—maybe I’ll come back around to the cheapo, tourist-y ones sometime in the future, but for now, the only kind I can imagine wearing are structured and slightly prim or funereal, like this one. If Harold from Harold and Maude were a hat, he might be this one.
I can’t believe I missed this hat when I made my post about clothes as armor. I’d wear this right now—the less hair, the better for this hat.
I like ear flaps on a hat, and this one showed me that that’s not a winter-exclusive proposition. Very contemporary gaucho.
Another hat I’d never even dreamed of before coming across it—I’d wear it with a long, black cotton dress with lots of lace or a Peter Pan-collared white shirt and jeans.
I love the subtle detail on this beanie, saving it from boring oblivion—makes me feel like a few choice stitches to pucker a place along the brim of a plain beanie could DIY it out of hat hell.
Love everything Jaded Made makes, and this hat is simply a sculpture.
Ending this hat hullabaloo with another Hurtence pick, on sale. Would look so good with a trench or camel-hair coat in the same creamy khaki as the base felt.
Hope every hair on your head is happy today, and if you have no hairs currently, my scalp salutes yours.
I might make a small commission if you purchase from some of the links above, at no cost to you! If you do, send me a pic of you wearing the item and I’ll comp you a month of HR.