Why can’t a guy wear a hat?

It’s cold, and I want a hat I can wear to work without looking like an idiot.

Used to, a guy could wear a hat. When you went to work, you wore a suit and a hat, and you looked sharp.

But something went wrong in the ’60s. Men’s hats suddenly fell out of fashion, and I don’t think they’re ever coming back.

Guys can wear baseball caps. Guys in Texas can get away with wearing cowboy hats. (Guys in Nashville can wear cowboy hats, too, but only when they’re on stage.) Guys can wear Santa hats if they’re out Christmas shopping. But a fedora? Forget it.

You wear a fedora today, you look like Jack Abramoff (left).

[Photo deleted.]

It’s a shame guys can’t wear fedoras any more, because a hat like that would be really practical.

It would protect you from the sun and rain and, when it’s cold, it would help you stay warm.

But guys who wear fedoras look like they’re trying too hard.

Sometimes,  a guy in a fedora thinks he’s Indiana Jones. Sometimes, he thinks he’s hip.

Sometimes, he’s thinking both things:

[Photo deleted. It was a picture of Shia LaBeouf wearing a fedora, but it wasn’t a scene from the last Indiana Jones movie. He was just wearing a fedora in public.] 

And that’s too bad, because guys need hats, and a baseball cap with a suit just doesn’t cut it:


26 thoughts on “Why can’t a guy wear a hat?

  1. Maybe you could borrow Thing 1’s football helmet hat?

    Only certain types of guys can carry off fedoras (think California or New York, not Mayberry!). Jim looks quite cute in a toque…


    1. I meant to mention toques, which people in the South sometimes call toboggans. I don’t know the etymology of that one.

      Golfers can get away with straw fedoras in the summer, there’s a sort of floppy fedora you can get away with wearing if you’re going fly-fishing. (If you’re going bass fishing, you gotta wear a baseball cap. I think it’s a law or something.)

  2. The young guys around here where their basecall caps in every different manner. Backwards, sideways, and some just a little off kilter. Just trying to be different. I love the fedora, Todd. If you like it, I say start wearing it daily until people are used to seeing atop your head. Quite smart looking! You could always resort to the lumberjack hats we see in Minnesota but then the thoughts naturally go to what you might do to them with your chainsaw…slasher movies…yuck!

    1. You mean one of those hats with the ear flaps? I always liked those. It’s not cold enough here in the South to wear one. My wife’s grandfather had a cabin in upstate Minnesota. If I lived there, I’d probably wear one every day.

      1. Those are the hats I’m talking about. Usually red and black checkered. Although now they are making them in a variety of styles and colors so you could even choose something that would match your coat if that was important! I remember the days when my Dad wore a hat to work. Very nice indeed!

  3. I am a HUGE fan of the Fedora, although that may have more to do with how it looks on Jon Hamm than anything else.

    But while we’re at it, why can’t women wear hats these days? Did anyone ever look classier than Ingrid Bergman in a hat? No. No one ever has.

    1. OK, look at the picture of Jon Hamm. Now, look at the picture of Jack Abramoff. Now, Shia LaBeouf.

      I think you’re mostly a huge fan of Jon Hamm.

      And you’re right about Ingrid Bergman. You’re not going to find a better-looking movie couple than Humphrey Bogart and Ingrid Bergman in Casablanca — and they’re both wearing hats.

      (You’re also not going to find a better movie, period, than Casablanca.)

  4. According to Dean Martin, “a hat’s not a hat till it’s tilted.” Maybe it’s just about the angle.

    Got to agree with the ladies’ hats too. Fashion isn’t the same without hats.

  5. I knew someone was going to write about this and do a better job of it before I could get to it.

    I was just noticing yesterday that it is getting cold enough for the headwear to make a showing and there have been such interesting choices. Ever since last winter I have wanted to write about Fisher Price Man. I just saw him last night for the first time this season. He must work in the same neighborhood and occasionally I see him pass by. He wears a cowboy hat that sits on his head in such a way that he looks exactly like the Fisher Price cowboy.

      1. There is a striking similarity in appearance. In fact, when you posted a picture of your Fisher Price man, I almost stole it. You know, public domain and all that. :-)

      2. I want to start a business where people can order custom made Fisher Price men.

        You can’t wear a ball cap with a suit…another reason we should abandon the suit altogether!

      3. There was a company a few years ago that would make custom action figures. They’d scan your head and make a little doll out of you. I don’t know if they’re still around, but this customer classic Fisher-Price person thing has potential!

  6. I have found over the years that hat wearing is often related to geographic location. Many, many, many people I have met that reside on the east coast wear hats. Hats and scarves – not just the knitted scarves that only serve to keep one warm, but fashionable, colorful and “texturey” scarves that oftentimes are worn simply to complement an outfit. I adore the fact that hats are no big deal where I live here in the suburbs of Washington, D.C. I love wearing hats. As for the toboggan, I was much embarassed to learn, in my early twenties, that the word toboggan, when used to refer to a knit cap, is technically incorrect and only serves to create an opening for those around one to gasp in amazement and to bend over with uncontrollable spasms of laughter. I have found that only my aquaintances that come from Indiana or Kentucky believe me when I foolishly inform them that I grew up calling my hat a sled. Geography is a fascinating subject. :-)

  7. I wish there was a way for guys to wear cool fedoras like the old days. My husband does not own a single hat that doesn’t make him look nerdy. Then there’s the whole “hat hair” issue – no one has found a solution for that yet.

  8. I was just thinking about this last night. I’ll wear a toque if I’m going out to a casual place — say leather jacket / hoodie formal. But if I’m going out to a place where I’d wear a pea coat/ nice sweater or button down, I question the toque, however cold. And if I’m wearing a top coat/ suit, the toque is out.

    It’s not like I got hair to keep me warm either….

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