Oh god, I don't want to be hat guy
October 2, 2012 3:21 PM   Subscribe

Oh god, hats. The fedora thread has made me aware that, as a baldish and getting balder guy, I should be wearing a hat outside, especially when driving as during the summer I'm inevitably in a convertible. Problems: (a) I don't want to be "that guy in the stupid hat" (b) I have a giant, round head.

Brimmed hats would seem to be right out, as I'm also relatively tall and my head sticks up into the airstream.

I cannot wear baseball caps, they just pop off my giant head, no matter their size. Lots of hats do. It's ridiculous.

Is there a flat cap I can wear without looking too goofy? I drive an old MG, so unfortunately I think a tweed flat 'at would just be begging for a pipe and a smoking crater where any self-respect I may have once had used to be.

Something that could be worn with jeans and a shirt is preferable. I would also prefer something that if I drove somewhere and then walked around in the sun I could continue wearing without looking like "that guy." (Maybe that's unavoidable. So be it, I guess.)

So: Give me hat styles to investigate, please. My hat size is 8 1/8 or XXL.

Also, in the current fedora thread, everyone mentions not wearing a hat inside, which I can be hip to...but what, exactly, am I supposed to do with it if I'm in a shirt and jeans? Carry it? That's fine, I just don't know what good manners suggests is appropriate.
posted by maxwelton to Clothing, Beauty, & Fashion (34 answers total) 5 users marked this as a favorite
I have to ask what specifically in that thread gave you the idea you must have a hat? (I'm not up on the thread and all...) Because I would actually say, besides my general lack of affection for hats, no hat is better than an ill-fitting hat. This kind of hat is probably the most likely to stay on your head and not look stupid, but depends so much on what your personal sense of style is. It would work well in the colder months with jeans and a tee, but during the summer months will make you look like a hipster.
posted by DoubleLune at 3:31 PM on October 2, 2012 [1 favorite]

I'm thinking the style of hat that Jason Mraz wears. They seem stylish yet still laid-back enough to wear with a t-shirt and jeans. Google images of him (if you aren't up on the pop singer trends).
posted by jillithd at 3:36 PM on October 2, 2012

When you go inside, you put your hat on the hatrack or coatrack. That's what it's there for.
posted by KathrynT at 3:36 PM on October 2, 2012

A watch cap, to me, doesn't go with a convertible. It's more of a "huddling against the winter wind in my peacoat" kind of a hat.

What about a Kangol? Kangol itself has an XXL, but says that works out to a shade under size 8; Borsalino makes a newsboy cap with a similar profile in sizes up to European 64, which seems to be a shade above size eight. I bought a fedora once for my uncle and his head was about your size; I found that you had to go a little high-end to find anything above an 8. You might do better now though what with the Internet and all.

Either that or just shave it down to military length, slap some sunscreen on your head and stay contently hat-less. I often think that a buzz cut looks quite well on a bald or balding dude.
posted by Diablevert at 3:43 PM on October 2, 2012 [1 favorite]

You are asking for a hat, I see that, but have you ruled out applying sunscreen? Goes with everything, won't blow off in a convertible, doesn't make you look like "that guy."
posted by ambrosia at 3:45 PM on October 2, 2012

Response by poster: I guess I was thinking that "best practices" seems to be covering up. Is there a sunscreen you can wear in your hair (or what's left of it) without it making it look like you've smeared a bunch of goop in your hair? Edited to add I do wear a buzz cut these days. Hm.
posted by maxwelton at 3:49 PM on October 2, 2012

I wear something like this when I don't feel like applying sunscreen to the ol' chromedome. Like you, I can't find baseball caps that fit, but these don't feel as ridiculous for some reason. And although Castro wears hats like this, I don't get the sense that people think I'm trying to be the hat guy for wearing it.
posted by burden at 3:51 PM on October 2, 2012

You're already a big balding man in an old MG. Man, just embrace it.

Not only do you need a driving cap, you need one in, like, patchwork tweed.

(If you ever take up pipe-smoking, I recommend a meerschaum, carved in the shape of a guy wearing a patchwork tweed driving cap.)
posted by box at 3:55 PM on October 2, 2012 [25 favorites]

What, really, is wrong with a tweed flat cap? It doesn't have to be tweed, though. You can get them in simple solid colors or linen for hot weather or even denim. They also conveniently often come in large sizes and there's no brim for you to be concerned about not being in the right ratio of width to your head.

This cap comes in XX-Large, and four different colors. It's liable to sort of fade into the background, because it's well-constructed and simple, and won't call attention to itself as being either too fancy, out of place, or badly made. That's how you avoid being "that guy".
posted by Mizu at 3:55 PM on October 2, 2012 [1 favorite]

How about a Greek fisherman's cap? Many of the images have the traditional grey wool but they are also available in black, navy and khaki, etc. canvas or cotton.
posted by likeso at 3:58 PM on October 2, 2012

My big very bald father used to do yardwork in a straw hat. Of course, he grew up on a farm so I think he felt very comfortable with it (psychogically). I suspect it provided shade/cover without heat buildup because it is very breathable (thus also being physically comfortable on a hot, sunny day).

For the car hat, I would suggest you take a friend with good taste shopping with you and get their opinion of what looks good on you. Though for your practical requirements, a beret comes to mind because you can fold it and stick it in your pocket. Some people look very dashing in them.
posted by Michele in California at 4:04 PM on October 2, 2012

There is already a handy guide for this.
posted by tel3path at 4:04 PM on October 2, 2012

Surely these are the only thing to be worn when driving a convertible?
posted by cromagnon at 4:18 PM on October 2, 2012 [5 favorites]

Flat cap, non-tweed.

I see nothing wrong with a hat with a brim. A trilby would be fine, but since we're talking about summer and sun instead of something you'd wear with a jacket, a panama hat might be better. A straw trilby would be OK, too. Maybe experiment with a pork pie, though I think the look is a little too late 90's Ska/extra from Swingers.

Steer clear of anything too formal or too wintry. Make sure you get something that matches most of your summer clothes. If you do decide to go with a brim, just go and properly try on hats at a real hat store. Pick something that actually flatters you. Get help from a sales associate if you're not sure. The main problem with dudes and fedoras, trilbies, etc. is that they just pick up the nearest available hat and wear it without thinking about the normal things one thinks about when choosing clothes. Ask the same questions you'd ask if you were shopping for shoes or jeans or whatever. Does this fit? Does this suit me? Does this match the clothes I already have?
posted by Sara C. at 4:31 PM on October 2, 2012

but what, exactly, am I supposed to do with it if I'm in a shirt and jeans?

Leave it in the car.

If you are sans car, just take it off and carry it while indoors. If you're going to a restaurant on foot, I'd probably err on the side of not wearing a hat that day. But if you must, maybe check it? Put it on an empty chair and don't forget it? Some restaurants have coat racks where you could leave a hat. If in doubt about the restaurant at all (will there be a coat check or rack? will we be able to get a 4-top?), just leave the hat at home.
posted by Sara C. at 4:36 PM on October 2, 2012

That's an great hat guide, tel3path. I have a long, thin (but also huge) head, a big nose, and big ears (that's right. I'm pretty much 100% weapons-grade sexy). It looks like it's a fedora for me.

Yeah, I don't think I can carry that off.

maxwelton - I have, as I mentioned, a huge head and although most baseball caps don't fit me, there are a few that do. Perhaps you just need to search a little longer.
posted by It's Never Lurgi at 4:38 PM on October 2, 2012

As a bald man, I can tell you that flat caps are the only caps I think look good on bald men. Find one that you like and go for it. I promise you won't be 'that guy.'
posted by saul wright at 5:26 PM on October 2, 2012

It looks like it's a fedora for me. Yeah, I don't think I can carry that off.

Flat cap. The man who posted his photo in this thread does not look like an asshole. You will not look like an asshole. Who does classic menswear in Seattle? Go there, try on hats.
posted by DarlingBri at 5:40 PM on October 2, 2012

Flat caps are great on virtually everyone. So taken am I with the Borsalino linked upthread that I may get one myself, plus it comes in Hats For Giants sizes.

Vis-a-vis hats indoors - it always looks a bit affected to me, but less affected when there's nowhere obvious to put the hat and the hat itself doesn't have a lot of brim or crown height. A tophat or even a homberg indoors looks pretty silly unless you're in very particular settings; a flat cap or a watchcap isn't as bothersome. I'd say it's probably worse to inconvenience your host by insisting on putting the hat somewhere when there's nowhere obvious available than it is to wear it.

In Peter Beagle's wonderful novel The Folk of the Air, Farrell is buttonholed by a very strange stranger at a cafe, and reflects that he wishes he wore a hat, because when you wear a hat and you pick it up to put it on, even the Ancient Mariner recognizes that you have to leave.
posted by Frowner at 5:47 PM on October 2, 2012

Dude, you're my age.

We're way too old to be "that guy in the stupid hat." We wear hats for utilitarian purposes, not as an affectation, or in some attempt to mold a "personality" out of the amorphous mass of our still-developing character.

We have character because we've lived. We can wear hats without looking like dorks because we're already past the point of much caring whether we look like dorks. Wear whatever dam' hat you want.

Having said that, I don't see how anything but some kind of flat cap is gonna stay on when driving a convertible.
posted by soundguy99 at 5:54 PM on October 2, 2012 [5 favorites]

My Mr has a giant round shiny head and he rocks the Kangols.
posted by matildaben at 6:20 PM on October 2, 2012

My brother has a giant bald head and he looks great in flat caps. My brother-in-law has a fairly large bald head and he looks OK in bucket hats/fishing hats.

Wearing a hat to keep your head shaded or warm isn't what makes you The Guy With The Hat; what makes you The Guy With The Hat is when you wear a hat as a fashion statement.

It's like sunglasses. Nobody looks like an asscandle when they wear sunglasses in the sun; it's when they wear sunglasses to look cool when the doucherie line is crossed.

My brother, who looks like a handsomer Michael Chiklis, looks like a million dollars in this hat. I promise that the largest size will fit your giant head, because it fits the brother's enormonoggin.
posted by Sidhedevil at 6:31 PM on October 2, 2012

I keep my hair cut short (I use a number 1 or 1.5 guide on the trimmer). My hair is thinning on top and I can't always wear a hat (a boonie) so I put sunscreen on my scalp. I've never noticed it once applied other than that my hair seems a little softer.
posted by VTX at 6:38 PM on October 2, 2012

Response by poster: soundguy99, point taken. I think I'll try a flat cap and see if I like it. It occurs that hats may have a bonus property in the winter of providing some insulation; I like driving the car on clear, cold days but it does get chilly.
posted by maxwelton at 6:44 PM on October 2, 2012

I think a flat cap would be awesome/adorable. I'm super-conservative in terms of men's dress and I don't like dudes trying to be all "oh, look at me! I'm unique!" And even I think it'd be totally appropriate and/or adorable.

"Also, in the current fedora thread, everyone mentions not wearing a hat inside, which I can be hip to...but what, exactly, am I supposed to do with it if I'm in a shirt and jeans? Carry it?"

First, inside is "a social or professional destination." It's nice/excellent manners if you take it off in line at the bank, but not required. You also don't have to take it off when you enter the lobby of an office building or in an elevator ... only when you get to the office you're visiting. So in theory you should only be taking it off places you'd also take off your coat and you'd have somewhere to put it. (Exception: You should always take it off indoors where kids (boys or girls) are wearing ballcaps, to set a good example. I have found that etiquette in schools is like 30 years behind the times in order to teach kids actual formal manners.)

If you're at a party, where are the ladies leaving their purses? Leave it there. Or on a hatrack. Or stuff it in the pocket or sleeve of your coat. Or if you travel with a female-person, their purse can be a great stashing-place. It's been common for 15 or 20 years for guys with ballcaps to stuff them into a back pants pocket, which means a lot of those guys are now in their 30s and it's socially acceptable (and more and more common) to stuff a hat into a back pocket, if the hat suffers stuffing. It's not elegant, but people accept it as a necessity and don't think it's weird, and you see more and more hat-wearing men doing that.

Carrying it in your hand is fine. Tucking it under your elbow (if it suffers folding/crushing) is fine. Putting it on the floor under your seat is fine. Most hat-wearing men I know put it on a nearby chair if they're in a conference-table sort of meeting with no hatrack or chance to get rid of outdoor clothes before the meeting, or on the table off to one corner. But really, absent a coat/hat rack, any place you see ladies stowing purses (under the arm! on the floor! on a chair!) is a good place.

If you see anything like this (especially in church!) it's a hat hook. Command adhesive makes them too, but they're hard to find.
posted by Eyebrows McGee at 8:15 PM on October 2, 2012

A hat to wear when you're driving your convertible is a separate category from 'that guy' hats. You're using it for utility, not as personality substitute, and it can live in the car when you're not driving. Get whatever you like as long as it fits and won't fly off your head on the freeway. Problem solved!

This is what I tell myself while I drive through town wearing a ladies white golf hat. WTH, it's more fashionable than a sunburn.
posted by Space Kitty at 8:34 PM on October 2, 2012

My husband wears a plaid fedora and he's not 'that guy'. He also has a giant balding head and yeah, a hat is the best way to stop both sunburn and winter wind burn. Frankly I roll my eyes at the metafilter fedora hate, I know several guys that wear natty hats of various descriptions and none of them are 'that guy' or any guy, they're all just normal people without much hair. I've never seen the attitudes outlined in that FPP actually play out in real life despite all the hat wearing guys I've encountered, maybe because I don't hang out in bars or whatever.

So I'd say go to a menswear store that sells hats and try a few on, both different types and different materials within each type. Buy the one that you like the most. The largest part of carrying off a hat is feeling comfortable with it being up there. If you don't think it's some kind of thing that makes you a manly man then no one else will either. And frankly, as long as you're not skeezing on young ladies you'll be fine regardless of what's going on on your head.
posted by shelleycat at 12:21 AM on October 3, 2012

Response by poster: I ordered one of these, as the price was low enough that if I end up feeling foolish wearing it I won't be too put out. And if I like it, I can move up from there if I want to.

Many, many thanks, everyone!
posted by maxwelton at 3:08 AM on October 3, 2012

I see you've already chosen a flat cap, and it looks nice, but I'm concerned about the logistics of a wool hat in the summer. If it were me (granted, I'm female with a lot of hair), I'd die of the heat in that. Even if you don't, your head might get sweaty and stinky (and so will your cap).

For a summer alternative, have you considered a bush hat? My brother-in-law and two of my friends (all of whom are totally or mostly bald) wear these in the summer for protection against sunburn. I bought one myself this summer as an alternative to my big straw beach hat, and I like it quite well for shade/avoiding sun headaches. They're cool, vented, and have the nice feature of being adjustable via drawstring, so the issue of fitting/staying on your big head will be addressed. They're collapsible, so they're easy to take off, carry around, stuff in a pocket, what-have-you, without getting messed up. I actually bought my cheap one in a Walgreens; you can order nicer ones from places like L. L. Bean.
posted by dlugoczaj at 3:39 AM on October 3, 2012

Big Hats for Big Heads
posted by Comrade_robot at 4:06 AM on October 3, 2012

Seconding bush hat. I froth with rage at hipster hats but it's mostly teeny trilbies with almost no brim that really set me off. A hat that you need because your poor scalp has inadequate protein to protect you? That is fine. Even better if it has enough brim to protect your neck and ears from summer sun and winter rain. The cap is a good start.
posted by gingerest at 4:21 AM on October 3, 2012

Here's how your figure out when to take your hat off. Imagine you're wearing a coat. I mean, not just a suit coat, but a big bulky winter overcoat or raincoat or ski jacket or something. (You might find that you're actually wearing that sort of coat. This makes it easier to imagine! Just look down!)

So then just ask yourself, would the situation normally call for taking your imaginary coat off? If so, then take your hat off too.

Actually I'm sometimes guilty of wearing coats indoors when it's not totally socially appropriate. And so what I do with a hat is, whenever I'm in a situation where I could imagine someone ribbing me for leaving my imaginary coat on ("What, leaving so soon?" "Hey, siddown and stay a while"), that's also a hat-removal situation.

Also, your hat goes wherever your imaginary coat goes. Coat's on a rack? Okay, hat too. Coat's in a closet? Okay, hat too. Coat's slung over the back of your chair? You can do that with the hat too if the chair has corner bits that stick up, or just set it on your lap or on the chair next to you. Coat's slung awkwardly over one shoulder? Okay, it's hold-your-hat-awkwardly-in-your-hand time.

The one specific exception to this is that for public prayers or blessings outdoors, your hat comes off and your coat stays on. But you knew that one already.
posted by nebulawindphone at 8:19 AM on October 3, 2012 [4 favorites]

Careful about bush hats. They magically look absurd in some places, and wonderful in others. I only know because I wear one. Picked up the habit in South Africa, after getting my head shaved for a cancer fund-raiser. LOL! Now I'm loosing the hair anyway.
posted by Goofyy at 8:25 AM on October 3, 2012

My late landlord Scott, who had a pretty sizeable noggin, used to wear a straw flat cap a bit like this one from an Amazon vendor, which comes in a range of sizes, looks pretty summery, and fits unobtrusively under your arm.
posted by tangerine at 12:45 AM on October 4, 2012

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