Hope me hat

October 19, 2021 6:57 AM

I have some nice hats (a black felt fedora, a straw Panama) but I don't wear them often, for two primary reasons: I am afraid the hat will blow off and I get wildly self-conscious. So, firstly, how does one keep one's hat on head while navigating (e.g.) a windy downtown? And secondly, how do you get comfortable with being the only person walking around wearing a hat?

I feel like I have to clap my hand on my head *very* frequently when I'm walking from the subway to work. I try to adjust my head angle kind of the same way I would adjust an umbrella but then I often feel like I'm peering out from under the hat. For situations where I'd like to relax, like a beach or a restaurant patio, keeping the hat from blowing away seems well-nigh impossible. I don't think I want smaller (tighter) hats, but maybe that's the solution?

And then there's the self-consciousness. I am a femme-presenting, 40-something woman. I'm pretty-enough but generally ordinary-looking, with my sole concession to nonconformity being occasional forays into primary-colored hair - ironically I feel much less self-conscious about having long, bright orange hair, possibly because once it's done there's nothing I can do about it besides cutting all my hair off (or, I suppose, having it recolored at great expense), whereas with a hat I can take it off whenever I want so I'm continually tempted to bail on the hat.

I wore the fedora to work today and I was very happy with how I looked in the mirror. I felt mostly OK about wearing the hat among strangers on the subway, but I am even more uncomfortable about wearing a hat among friends! Part of this is that I have bit of fear of coming across as a try-hard.

Is there any hope for me? Can I become a hat person? I like the way brimmed hats look and I like that they provide my face with a little bit of extra protection from the sun. It would be nice if I could get comfy with having them as a regular part of my wardrobe.

posted by mskyle to Clothing, Beauty, & Fashion (21 answers total)

Pretty sure the conventional way to keep a hat on from the days when everyone wore hats was a hatpin.

As for how you feel about it, I sometimes remind myself that nobody (at all, ever) notices or cares nearly as much about my appearance as I do, ymmv.
posted by SaltySalticid at 7:11 AM on October 19, 2021 [6 favorites]

For me hats are about sizing: a friend used to give me his hats, but his head was enough bigger than mine that they just won't stay on. So - if you have long hair, hat pins are groovy, but if not then you're going to have to pick hats that stay on your head and that probably means smaller hats.

For the self-consciousness - mostly what I'm getting is that the hat feels like a really big deal to you even though other people will probably not pay a lot of attention to it, and you feel at some level like you can't rock this look and so shouldn't try. I don't know how to fix this, but I think what you may want to work on after securing the hat to your head is just how to feel comfortable in it. Would it help to wear the hat around the house, or other places where you can just enjoy the hat and kind of get used to wearing it? What about treating the hat like a favorite pair of socks, or matching it to something? "I always wear my hat with these socks!" kind of thing? Maybe you have a friend locally who can encourage you to wear it, or who will wear hats with you?
posted by bile and syntax at 7:20 AM on October 19, 2021

OH! That's what hat pins were for! I just... somehow accepted that they were a thing that could be deployed as needed in a certain type of novel with a certain type of intrepid Victorian heroine, and never really thought any more about it.

I'm not a hat person, but I have a brimmed hat that's secretly waterproof, and I think it looks very stylish with a long coat (rain- or otherwise). I'd feel more self-conscious if I wore it with a short jacket or no coat at all. The fit is what keeps it on my head, and it's expected to be worn in blustery wet weather, so it's got an adjustable strap on the inside so that it can be worn as tight as conditions dictate.

It's perfectly comfortable - I can wear it all day - but the downside of the tight fit is that it leaves a visible mark across my forehead when I take it off, and I feel a lot more self-conscious about that than I do about the hat itself. So I'm more likely to wear it for a day of walking on the marshes or wandering around a city by myself than on the way to work.
posted by ManyLeggedCreature at 7:43 AM on October 19, 2021 [1 favorite]

Response by poster: I will add that maybe my head is also a weird shape? I can't keep headbands or knit hats on (they just slide right up my head) unless they come down to my eyebrows.

(I don't know how I missed this before but I did just find this YouTube video about how to keep hats on, which is more aggressively vintage-styled than I am wanting to go but I guess there's not harm in searching Etsy for hatpins! How do men do it though?)
posted by mskyle at 7:45 AM on October 19, 2021 [2 favorites]

There are a bunch of different techniques but I think a common one is to sew an elastic band into the hat, there are a ton of tutorials on YouTube.
posted by muddgirl at 7:50 AM on October 19, 2021 [1 favorite]

It may also be about the texture of your hair and/or hairstyle. Long, open, sleek and freshly washed hair makes it harder to keep a hat on.
posted by 15L06 at 8:05 AM on October 19, 2021 [1 favorite]

When I interned in a theatrical costume shop, we did 'quick and dirty' hat sizing by fitting an elastic band so it sat comfortably on the wearer's head, and then sewing it to the inside hatband by just tacking it at a few points. We used the kind of elastic that had rubber gripping texture on one side, which did exacerbate hat-hair issues. So this was only for hats that remain on through the performance.
posted by buildmyworld at 8:11 AM on October 19, 2021 [1 favorite]

How do men do it though?

My dad was probably one of the last of the old-time hat wearers. He would get hats sized to fit him - since he had a large head, he had to special order them. When The Great Gatsby came out in the 70s, I went with my brother to god knows how many stores trying to find a Gatsby hat big enough for him. I would expect having a hat made to fit your head to make a difference. I have a bunch of the old-fashioned ladies hats, and they were more made to perch daintily on top of the head. Thus the need for hat pins.

(I love this question. I have some of my dad's old fedoras and really want to wear them, but I feel too conspicuous.)
posted by FencingGal at 8:33 AM on October 19, 2021 [1 favorite]

In the olden days, hats came in different sizes. So you got one that fitted. I have a cloche hat and a baker boy cap that I wear sometimes in the (British) winter, and both of those stay on my head but that's partly down to the shape as well as the size. If you're wearing a hat like Kate Middleton wears, then she uses either or both clips inside the hat or a hat elastic that goes under her hair at the back. Hat elastic might not be a terrible solution for you if you have bobbed or longer hair.

In terms of wearing a hat, I think that you have to just be confident in your overall look. And then not get too hot. It's not that unusual to wear a hat.
posted by plonkee at 8:54 AM on October 19, 2021

How do men do it though?

As a man with peach-fuzz length hair, the answer is "make sure it's really tight", to the point where it can leave crease marks on my head. This will sometimes include sewing an extra layer of material and/or elastic band into the band area.

And the hat will loosen up a bit over the day from my head stretching it out plus (I assume) body heat.
posted by soundguy99 at 9:08 AM on October 19, 2021 [1 favorite]

Best answer: Male, shaved bald (so I wear hats all the time), but I keep hats on by buying ones that fit: They should slip on easily when pulling evenly, but be tight enough that if you lift with just one side they bind a bit (this last weekend I was wearing a very comfortable fedora that my 8 year old niece decided she was going to appropriate, so she climbed on my back and started yanking, and couldn't get it off because she wasn't pulling evenly). I have worn well-fitting felt hats while out whale watching on the Pacific Ocean, as the 40MPH wind and spray blew all around, because they fit.

And, yeah, head shape may have something to do with that. But I have a long history of hats that were either too tight or too loose (I also have a huge head, so finding hats that fit me is pretty rare).

As for feeling comfortable in them: A few years ago I went off to a full-weekend event (square dancing), and as I got about an hour away from home I realized that on my way out of the house I had managed to grab a mismatched pair of shoes. I wasn't gonna drive home, so I decided "fuck it, I'm gonna wear the hell out of these mismatched shoes".

It was so successful that it has has now become a bit: I deliberately buy matching styles in differing colors for square dance weekends, and if I show up with matching shoes, people ask.

If I can wear mismatched shoes, you can rock an elegant hat. Take that space and own it. And a woman in a wide-brimmed '30s-'40s fedora? Holy crap yes.
posted by straw at 9:29 AM on October 19, 2021 [2 favorites]

Response by poster: They should slip on easily when pulling evenly, but be tight enough that if you lift with just one side they bind a bit

Ah, this is actually super-useful! I believe my hat is the "correct" size for me according to my head measurement and the manufacturer's size chart (non-adjustable one-size hats are generally way too small for me - they either perch on top of my head uselessly or wedge onto my head uncomfortably). But! with the hat firmly on my head I can give it a good tug from the front without it moving, *but* it's easy to dislodge from the back. So it might be a little too loose, or it might be my hair being slippery at the back of my head, or it might be my head shape or some combination. I may try just adding a little sticky elastic at the back as a first resort.

Thank you all for your suggestions!
posted by mskyle at 10:08 AM on October 19, 2021

Best answer: In my experience, the only way to get over the self-consciousness is to keep wearing hats. It will take longer than you expect for it to feel natural (or if not natural) then not something you're worried about. I'd say it took me a few years to reach that point, but I was much younger (and more self-conscious in some ways) but in conflict with that I really, really wanted to wear hats, which mean I was at odds with myself. I'm happy that my hat-wearing side finally won.

Even if a hat fits properly, a good gust of wind can still blow it off. But you'll be quickly enough (in most cases) to bend down and pick it up before it gets too far. (Note this doesn't happen very often at all.) I've only ever lost one hat and that was a cheap straw hat that didn't fit very well that I wore on the beach. The wind grabbed it and took it way down the beach, and the thing just kept going.
posted by sardonyx at 11:19 AM on October 19, 2021 [2 favorites]

Guys might wear a short connector called a hat trolley or wind trolley, that clips to the hat and to his collar -- much like an "idiot string" for mittens. :7)

As for fit: it's worth finding out whether your head is a "long oval" shape like mine. Most quality hats are made for people with a wider & shorter skull than yours. This can be misleading because they are sized by circumference, but not by shape. So your head might be the same measurement of someone else -- but if one of you is a long oval, then your hats won't be interchangeable. And since most hats are not long oval, it limits the choices for those of us with *cough* such a lovely, superior form.

I have a nice Akubra hat that I wear outside. I really don't care what people think: I am wearing it to prevent skin cancer, and that registers with me as far more important! :7) So you do you, and wear what you like.
posted by wenestvedt at 12:13 PM on October 19, 2021 [2 favorites]

Hats are good, Hats look good, and only snobs don't like how they look. You should wear your nice hats on calm days.

Now that I'm older, I mostly wear a Tilley-style knock-off bird-watcher hat with a loose neck string outdoors on windy days (and my beat-up old panama on calm sunny days). This style kinda implies not trying to be stylish (some Tilleys look pretty good tho). Also, bird watching is fun.
posted by ovvl at 4:55 PM on October 19, 2021

Just popping in to say I'm a person who would see you on the street or subway or at a bar and think, "Damn! That person has such style! I should wear a hat!" I know (not believe, know) we, people who admire hat-wearers, are legion. I hope you can get more comfortable about wearing your hats.
posted by Ink-stained wretch at 6:47 PM on October 19, 2021 [3 favorites]

In The Adventure of the Blue Carbuncle, Holmes refers to a “hat securer,” but they seem to have fallen out of favor since the late 1800’s. Using that as a search term does turn up some patents and the mitten-retaining gizmo an earlier post referred to.
posted by Gilgamesh's Chauffeur at 9:58 PM on October 19, 2021 [1 favorite]

And then there's the self-consciousness. I am a femme-presenting, 40-something woman

So there are a lot of negative stereotypes out there about fedora-wearers, and I think you might have picked up on some of these.
Fedora Guy
https://www.gq.com/story/the-bad-hats-of-tinder
What do women really think of the oft-mocked 'fedora personality'?
However, these are by and large stereotypes about male-presenting people wearing fedoras. As a femme presenting person your wearing of a fedora has a different context than this, unless you are leaning really hard into picking up women by negging them or something. Note that I'm not saying that there is anything wrong with a male-presenting person wearing a fedora as a personal accessory, just that it happens to come with more cultural baggage to contend with. As a femme-presenting woman these stereotypes don't apply to you, just as many stereotypes faced by women wearing various feminine-coded clothing items often cease to apply if the same clothing is worn by a burly bearded man.

how do you get comfortable with being the only person walking around wearing a hat?

Maybe you can visit a place where more people wear hats? This might even be just a different part of town than usual. I wear hats pretty frequently myself and haven't felt like other people treat it as something unusual or that I'm the only person wearing a hat, and if I'm wearing a nicer hat sometimes other hat-wearing people come up and ask where I got my hat (I usually send them to the local hat shop, because what they really want to know is where they themselves can buy a nicer hat, not that I bought my hat somewhere far away). Maybe just visiting a hat shop might make hat wearing feel a bit more normalized to you - surely if you are in a city large enough to have subways there must be a hat shop, if not several hat shops?

For the blowing away issue, sounds like your hat is mostly fitting properly, but you might try adjusting the angle on your head. (or if you want to throw money at this issue, you can buy a custom made hat for your specific head shape) If you can get it to sit slightly below the widest part of your head it will stay on much more easily. Also, increasing the friction of the hat against your head can be helpful. I see several answerers have offered suggestions around modifying the hat for this, but you can also increase the friction of your head by using hair styling products.
posted by yohko at 2:45 AM on October 20, 2021 [1 favorite]

Response by poster: Thank you all for your suggestions and encouragement! I've marked a few "aha" moments as "best answer" but I appreciate all of it.

Update on my first day of felt hat-wearing: it was still breezy but dramatically less windy when I left the office, and I think I may have just had the misfortune of wearing the hat for the first time on a particularly windy morning. Also a woman said "excuse me, sir" to me later in the evening which was briefly startling* but I'm guessing is something that happens if you wear a black fedora in a neighborhood with a highly visible Orthodox Jewish population.


* last time someone called me "sir" was when I went to Sandals (the couples' resort) with my sister
posted by mskyle at 5:53 AM on October 20, 2021 [3 favorites]

My Akubra hat came with some strips of white felt, which go behind the sweatband in order to make it fit more snugly on my 'uuuuge 'ead.

You might try something similar.
posted by wenestvedt at 12:17 PM on October 20, 2021

This is the exact thing the phrase "hold on to your hats" refers to.
posted by Billiken at 12:31 PM on October 20, 2021