My first “real” cowboy hat love started life crushed crown down in a milk crate at a garage sale outside Greensburg. Buried under a pile of schlocky looking fishing hats no one wanted. Soft as hell in that way only a decades-old hat worn properly will get. Not like the wrist-sandpaper bruisers you find artificially dulled out at retail these days. Sweat stain inside the crown band, the good kind. Nearly walked past because one side was mashed flat in the brim and I assumed it was totaled.
Flipped it over out of curiosity, found a vintage stitched-not-printed Resistol label inside. Suppered out the brim with a kettle and about fifteen minutes of patience I didn’t know I possessed.
I bring that up because when I picked it up to finally bring it home the woman manning the table—having eyed me down through perhaps a dozen garage sales by that point—asked if it was for my wife. Casual conversation question, not weird asked-to-get-polite-but-really-just-nosy at all. But it occurred to me how much hangs on that one simple ask, whether a perfectly good hat constructed on a men’s hat block is implicitly some sort of no-go for women who feel like wearing them. Which is a ridiculous question at heart, because a hat doesn’t care who wears it. But it’s asked so universally that we should probably dig into what is actually true about it and what’s just idle/customary sexism.
The sizing issues no one chats about until they try to buy a hat
The honest things that matter, which actually has nothing to do with semantics and everything to do with math. Men’s hats and women’s hats, when hat makers care to distinguish between the two at all, are traditionally constructed on different-sized oval hat blocks. That, y’all is the official term for it. The oval. The template manufacturers use to cut out the head opening on a crown of felt or straw. Men’s hat sizes tend to run rounder, fuller. Many women’s heads are slightly more oval, and can be smaller circumference, which wouldn’t matter if you didn’t put a men’s size 7 1/8 on someone with an actual measurement of 21 and a half inches around and then watch the hat perch on their ears for dear life.
Crown height is the second hang-up. Older men’s hats, particularly from the mid-century through the Seventies tend toward a taller crown size than you might expect. Four and a half inches, five inches, six before anyone’s had a chance to shape it down yet. Taller crown on a smaller head can overwhelm the features of someone wearing it, again making the hat look top-heavy and oversized. I stumbled across this gorgeous open road style Stetson last summer, massively tall crown, huge brim and couldn’t get over how well it looked on the hang Tag and … not at all on roughly half the dudes who tried it on at our hat swap table because of proportion, not gender discrepancy.
Brim width is another factor but in reverse. Too narrow a brim on a woman or person with a smaller frame can have the opposite effect, making their head look disproportionate to their shoulder by comparison. Fun to actually look in a mirror at side-on when trying anything on, feels weird at first because we’re used to judging hats as if we look at them from straight on 100% of the time IRL, but it’s the side-angle that sells you on whether or not the proportions are fighting each other.
And then of course there’s hair. Which is the bizarre exception in all of this because it doesn’t matter what hat block you start with, if someone is buying a hat to cover a full head of hair it’s going to change how that hat fits them. But it applies more often to women wearing a men’s hat with the expectation that they can get it to fit as if there’s nothing under the bill because companies traditionally cut their hat blocks based on hats sitting on naked scalps or very short hair.
Why we should have known the real answer wasn’t about asking permission anyway
Once you get through all that sizing nonsense the question of is it EVEN ALLOWED starts to sound pretty dumb,TBH. There’s no barcode scan at the hat ranch. The women I know who rock a men’s cowboy hat and can’t be bothered even trying to look like they cognizant of the silliness of wearing one look that good in them because they Found The One that fits, not despite the hat being cut for a man’s head but because somebody took the time to size a hat block close enough to their actual measurements that it sits on their noggin the way it was intended to sit. Confidence has nothing to do with it, though being confident in your eventual choice sure doesn’t hurt. It’s about fit above everything else, just like it is for anyone walking into any establishment looking to purchase clothing.
I’ve sold men’s straw boaters to women, cowboy hats to women. Nothing against either, I love shirts and hats on anybody who rocks em right, but the cowboy hats that work for women going big in a men’s size are almost never the largest brim styles or the mushiest crown you have on display.
They’re the ones where the purchaser takes the time to actually try it, tip it, walk around with it on for a minute rather than clutching it to their forehead and peeking at themselves in the five-inch circle of reflective bathroom retail-mirror before deciding it “just doesn’t feel right.” Something that large and tall that isn’t sized properly will fall down your forehead and look like cosplay. The same hat, sized with care will look like it was made for you.
If there’s any takeaway to this entire thing it’s that men’s and women’s labels on a cowboy hat were likely applied because it was easier manufacturing-wise from the jump and not because anyone’sowing a hat in 1952 stopped to consider it a hard-and-fast rule. Classic hats especially were built without that level of gender-exclusive nonsense in mind. Block cutter cuts a hat block,_FACTORY_BUYSLOTS OF STUFF MADE ON THAT BLOCK,_somebody walks out with a hat that fits their head. Repeat. It still works that way today, generally. Try hats on first, curse at the size chart second. Problem solves itself.
Callum has spent ten years digging through car boot sales and charity shops in Glasgow. He writes about vintage menswear and old workwear, and he’s happiest when he’s found something good buried at the back of a rail.
