I don't want to be that guy.

January 19, 2009 5:26 PM

MadHatterFilter: Will I ever get to have a fedora without looking like a dork?

I'm a hat guy, been such since a little tyke. I have a great Panama, a couple of Akubra's, a small mountain of ball caps, hiking hats, rain hats, you name it.

But no fedora. At least, not since I was six.

Now that I've crossed the 50 mark I'm starting to wonder if I can pull off the fedora without seeming like its an affectation? I'm not a kid in drama club trying to act all Brat Pack. I be all growed up now (on the outside).

So, what's the hive opinion? Are fedoras only for the dorks and great-grandpa's? Or can they be worn by a guy who loves hats?

posted by trinity8-director to Clothing, Beauty, & Fashion (37 answers total)

I've seen guys who pull it off, though it's probably not going to work for most people. It's hard to say without seeing a picture of your head!
posted by Dee Xtrovert at 5:42 PM on January 19, 2009

Please where the hat that you want to wear. You will look very handsome in it.
posted by moxiedoll at 5:42 PM on January 19, 2009

Not in the States, at least. They're outmoded, and as such any actual wearing of them will be an affectation -- and seem as such. However, at 50+, I imagine the innate social respect you command will outweigh the minor social awkwardness of adopting an older fashion, should you choose to wear one.
posted by ellF at 5:42 PM on January 19, 2009

Fedoras can definitely be worn by a guy who loves hats. My 38-year-old boyfriend, who loves hats, wears one all winter and looks super hot with his wool winter coat on. Go for it!
posted by snugglebunny at 5:43 PM on January 19, 2009

I'm all in favor of more people wearing the hats they want to wear-- otherwise, I wouldn't own a drover hat. I'm hardly a fashion plate, and people still accost me and go "oh my God, I love your hat!" all the time.
posted by fairytale of los angeles at 5:47 PM on January 19, 2009

If you are very good looking you can wear whatever you want and it will look "good." If you are a borderline case, a fedora may be seen as trying too hard. Or, you could be an average looking guy with the special spark that makes whatever you wear cool. Without a photo there is no way to conclusively tell.
posted by Optimus Chyme at 5:49 PM on January 19, 2009

Perhaps with a certain jacket. Perhaps best with a jacket with the sleeves rolled up, very much an 80's throwback. Definitely not with shorts. Definitely not with shorts cut above the knee.
posted by ezekieldas at 5:50 PM on January 19, 2009

The key to the fedora, which most of those drama kids who wear it forget, is that you must pair it with appropriate clothing. Wearing it with your black Sisters of Mercy t-shirt will make you look like a d-bag, wearing a brown fedora with a nice yellow dress shirt makes you look stylish and smartly dressed.
posted by Loto at 5:50 PM on January 19, 2009

Mr Mumstheword looked like a dork when he tried on a fedora as a young punk...however, recently (he's now a youthful fifty-ish, like you) we chanced upon one in a secondhand store, he donned it...and voila! Frank Sinatra reborn. I'm getting it for him for his birthday. It was a retro version, in dark brown, (probably from the fifties or early sixties, and made of beautiful felted wool) so it's the real deal. At any rate, he is now adorable in a fedora, where formerly he was simply a callow youth playing dress up. Now he has what it takes....I'll wager you do, too.
posted by mumstheword at 5:51 PM on January 19, 2009

Nah, go ahead and rock it. That's assuming you usually dress formally enough for the fedora to match. Or you dress eclectically enough that one more weird item is irrelevant, which is my approach.

Mind you, this is coming from a twenty-five year old who frequently wears a beautiful Stetson fedora.

Hats are basically out, though, thanks to JFK. At this point, I think just about any hat style but the baseball cap stands out as an anachronistic or nostalgic choice--and is viewed as an affectation by hipsters and fashionistas who can't cope with the concept that some people just like certain kinds of clothing. And all those beautiful styles of hat that you adore are unlikely to come back even if hats in general do, since a nice fedora (or Panama) requires care and consideration that most people of my generation are unwilling to invest. Furthermore, most restaurants and similar establishments have long ago divested themselves of their hatstands, so your hat winds up taking up valuable space on the table.
posted by Netzapper at 5:54 PM on January 19, 2009

For an indication of why fedoras can be a hard look to pull off, the famous fedora guy thread is worth glancing at.

Ever since that thread, I've noticed people wearing fedoras. Mostly, it ends up looking like an affectation, and not a real stylish look. But maybe one time in ten, there's someone who really nails it. So if you can be in that stylish ten percent, then by all means wear the fedora.

But get some honest assessments before making it a part of your daily outfit, because when it fails it can really fail.
posted by Forktine at 5:55 PM on January 19, 2009

The mister manages to wear a fedora (and my granpa's Homburg, and a straw bush hat) without looking like an ass... and he's 29. I think it's partly his demeanour tho. He's an engineer and quite geeky and quiet. And he is, and always has been, a Hat Guy. Hard to explain, but he receives a lot of compliments on his sense of style, so there is that.

What I'm trying to say is: if you like it, wear it, and don't feel selfconscious about it. In other words, "own it", without having it own you.
posted by lonefrontranger at 5:58 PM on January 19, 2009

There are a small number of guys who can pull off wearing a fedora. If you aren't sure you are one of them, you'll probably look like a dork. It's like poker: If you sit down at a table and can't tell who the fish is after fifteen minutes, you're the fish.
posted by Justinian at 6:00 PM on January 19, 2009

I remember a friend's dad wearing a fedora to work every day (this was in the nineties), and I thought and still think he looked really good--he'd have his suit on and a trench coat or overcoat, and the fedora looked a little old-fashioned but also pretty cool. It was like the male equivalent of a nice piece of vintage jewelry. I think if you're over 30 and dress nicely, a fedora can look great. It's the obnoxious 20-something guys who are all "look at me! look at my fedora! I am interesting! I am sooooo unique!" who shouldn't be wearing them.
posted by Meg_Murry at 6:03 PM on January 19, 2009

I inherited my first fedora when I was 17. I've worn them off and on every since.

I think if you like the hat it will show. If you feel awkward and dumb in it that will also show.

Typically, I wear mine only with my wool overcoat. The hat in of itself won't work if it doesn't have the matching fashion. Honestly, I'm more comfortable in button shirts than I am in t-shirts. About the only time I feel like a dork in my hat is when I'm not wearing the right clothes with it.

Try one on, see if you like how you look. If you do, buy it.

And good God, man, you're 50, it's about time you start sporting some affectations already.
posted by cjorgensen at 6:06 PM on January 19, 2009

I am an ass.

I wear both of my grandpa's fedoras, a bowler, driving caps and a real, old school beanie.

Own the dorkiness (or assiness or whatever it is). Do you care what other's think? If so, don't do it unless you are one of the super-cool people others mention. If not, wear the hat you like and when people guffaw, tell 'em to fuck their nasal cavity with a phillips-head.

But then, I recently got me a wind-up pocket watch, so my advice is generally not considered normal.
posted by Seamus at 6:08 PM on January 19, 2009

Meg_Murry is correct.


Since your wearing of a fedora wouldn't be an affectation, it won't look stupid. Just make sure it's a nice one, dress appropriately, and enjoy your fedora.
posted by Neofelis at 6:09 PM on January 19, 2009

I definitely think that your age bracket will help it look far less like an affectation. Give it a shot, if your friends avoid eye contact when you are wearing it, there's your answer. :)
I really just wanted to chime in to encourage you to read Forktine's link to the fedora guy thread, it really is some of the funniest stuff I've ever seen here.
posted by 8dot3 at 6:51 PM on January 19, 2009

Fuck the haters. If you like it, if you like the way it looks on you, then go for it. As people above have said, if you own it (as in make it yours, not as in legally possess it), it will look good on you, and anyone who doesn't approve probably isn't someone worth your time anyway, at least socially. And at fifty, I imagine that you've got enough professional capital that it's not going to matter to your place of business if you start wearing a fedora, whether they think it's an affectation or not.

(For the record, I'm 25 and wear a fedora, and I don't care what the rest of y'all think.)
posted by Caduceus at 6:55 PM on January 19, 2009

I've always wanted to wear one as well however, I suffer the same afliction as youself. I look back at footage from the 20's to the 50's and stare in jealous wonder at the sight of every man wearing a fedora or other such hat as he goes about his business.

Recently I've found a place that sells the same hat that Indiana Jones wears and I've been lusting after it ever since.

My problem in Australia is there are not many occasions where you need to get around in a big coat and I don't wear a suit to work any more. Although Dr. Jones rarely wore a suit with his and always managed to look extra cool, he was surrounded by professional costume and lighting people and always had someone on hand to make sure his rugged manly beard always looked rugged and manly to match his hat.

Maybe the answer is to start wearing them while doing the gardening at home where it is relativley safe from ridicule. Then we could venture further and further from the back yard until we are proudly strutting down the High Street in our felt hats.

The day is soon approaching where I will just go out and buy one and damn the torpedos!
posted by Man_in_staysis at 6:57 PM on January 19, 2009

You'll stop looking like a dork when you stop caring about looking like a dork. Wear the hat. Fedoras are at the intersection of functional (warm, sheds rain) and fashionable.
posted by theora55 at 7:11 PM on January 19, 2009

It's your head. Put a hat on it if it makes you happy. Don't think about it too much.
posted by chairface at 7:18 PM on January 19, 2009

It depends on what you are wearing with it. If you are wearing a business suit and/or overcoat, you can pull it off. Certainly when you reach 60, you can do whatever you want and call it old age craziness.
posted by JohnnyGunn at 7:33 PM on January 19, 2009

Hats are not generally cool, other than certain overbent bill baseball caps etc. So, the general trend is not cool, but to be cool you certainly do not need to follow the general trend. You have to make your own personal trend. The fedora itself is not enough, but you probably already know that. If you have a certain personal style that has appeal you can integrate just about anything as long as it fits well with the rest of your style. Because fedoras are out of the style norm you have an extra high burden of integration. Yet, it is far from surmountable.
posted by caddis at 7:36 PM on January 19, 2009

"Outmoded" refers to fashion, not style. If you have a sense of style, you can wear whatever you darn well please. Personally, I have a lot more respect for people who clearly enjoy dressing themselves than I do those who only worry about what other people think or if something is in fashion. If you think it looks and feels good and it's not wildly inappropriate for the situation (black tie event, sailboat regatta, the gym), wear it.
posted by oneirodynia at 8:16 PM on January 19, 2009

If your hair is gray, yes. If your beard is gray, double yes. If your hair is not yet gray, or you don't have a beard, sorry no.
posted by zpousman at 8:19 PM on January 19, 2009

"YES YOU CAN!"
Life is too short to worry about stuff like this. The world is too cookie cutter as it is. Wear your hat (any hat) LOUD & PROUD. There are no rules. It's all about confidence. If you think you look silly, you just might convince everyone else.
posted by sequin at 8:55 PM on January 19, 2009

If you want to look "right" in a fedora, you need to be wearing what people wore with them- a suit. I don't know my hat style too well, but my memory says that the fedora is a fairly formal, cool-weather hat. I remember something about there being a certain day when it was socially acceptable to switch from a fedora to a lighter summer hat.

I see plenty of business-types walking down the street in the business area of the city wearing fedoras, and they don't look out of place at all. But they are wearing suits, and probably overcoats.
posted by gjc at 9:00 PM on January 19, 2009

Fedora Guy! Yes, that was exactly what I thinking of wrt the negative side.

Thank you all for your input. I agree that the right clothes are a must. A topcoat of some sort feels right (he says lusting after the long, cashmere coat at Nordstroms). Thankfully, Seattle weather makes those appropriate much of the year.

My hair is has more silver (yes, silver, dammit!) to it than brown these days. I remember a hat store downtown. Might have to pay a visit there soon if it is still in business.
posted by trinity8-director at 9:14 PM on January 19, 2009

My boyfriend of 30 wears a trilby, which is a step removed from a fedora. He will wear it with a buttoned-down shirt, a sweater, or even a t-shirt. What makes it work for him (and it is generally agreed he can pull it off) is that he doesn't CARE what other people think of him and his hats. And that makes all the difference in the world.
posted by Windigo at 9:43 PM on January 19, 2009

I remember a hat store downtown. Might have to pay a visit there soon if it is still in business.

Byrnie Utz Hats
310 Union St
Seattle, WA 98101
[phone]

It's where I got my Stetson years ago; and it seems like it's still in business. I adore that joint. And the name.
posted by Netzapper at 9:47 PM on January 19, 2009

Can you pull off a (tied) bow tie? A three piece suit? Suspenders? Tortoiseshell spectacles, cufflinks, tutones? (not necessarily simultaneously.) if this sort of foppery fills your closet for dapper occasions and makes your heart go pitty-pat, then yes, you can pull off wearing a fedora and probably you can look good in anything else that strikes your fancy.

--married to one.
posted by Lou Stuells at 10:02 PM on January 19, 2009

Byrnie Utz! That's the spot. I used to walk up there every so often when I worked in Pioneer Square. Classic place.

Lou Stuells: not the tortoiseshell specs or tutones but I have or have done all the others.
posted by trinity8-director at 11:28 PM on January 19, 2009

well in that case, run with it! Guys like you are a ball to shop for :)
posted by Lou Stuells at 8:09 AM on January 20, 2009

Oh, wear the damn thing with whatever clothes you want. Though you may wish to consider the color of the coat uyou wear most often with the color of the hat. Any maybe your pants, too.

And consider hats other than fedoras: Akubra makes lots of different things these days. I wear a Cattleman, but I bought it sight unseen and now wish I had half an inch less in the crown. Different hat shapes match better or worse with different head- and body shapes. (Also, you may be a Long Oval, so try on a hat before you buy it.)

I had a fedora for a dozen years that I was always too timid to wear out of the house. But I secretly wanted to. And when I finally did, I loved it!

man_in_staysis, how come you can't find an Akubra you like?
posted by wenestvedt at 9:27 AM on January 20, 2009

Buy a high-end fedora, one with a good cut that fits your head as it should.

The generic stuff will ALWAYS end up looking cheap.

It's worth checking vintage/resale places too - usually better made and made for the era as opposed to costumey throwback.
posted by HolyWood at 2:09 PM on January 20, 2009

Do it. Not enough guys who are interested in wearing a hat *well* wear hats.
posted by fantine at 2:58 AM on January 26, 2009