How to wear a hat

Being at Game Developers Conference last week was almost comforting. People were wearing hats! Lots of hats. Granted, this is mostly because the creator of Minecraft sports the “dashing I.T. pro” look, but it’s always nice to see a bit of millinery appreciation in action.

Unnnnfortunately, the show also served a chilling reminder that wearing a hat is more complicated than “grab crown, place atop head, orient peak forward, secure headband around skull.” It’s all well and good that you admire Indiana Jones, sir, but part of why everyone thinks Indiana Jones is dashing and cool is because he did not wear his fedora with a free swag T-shirt from the Nvidia booth. A hat is like any other kind of accessory and needs to be matched by the rest of its ensemble! Unless you are a cute girl (which allows you to wear any damn thing you want and get away with it), you need to avoid wardrobe dissonance. Just as you don’t wear a tie with a polo shirt, nor do you tuck a starched white button-down into a pair of cargo jorts, you have to be mindful of the gestalt of what you’re wearing before putting anything atop your head.

For your convenience, I have selected five different styles of men’s headwear — top hats, classic fedoras, trilbies (short-brimmed fedoras), flat caps, and ball caps — and placed them on what I call the Sliding Scale of Fashion Formality. Gauge the dressiness and overall put-togetherness of your apparel and hat up accordingly!

Of course, there is a great deal of variety even within these styles of hat. A really nice professional-quality woolen ball cap works higher up the scale than a cheap mesh cap with a foam front. (Blinged-out Ed Hardy-style ball caps are never acceptable, however.) Flat caps can range from very simple to very ornate and stylish, and you might be able to get away with wearing one right up to the edge of “business” level apparel if it’s nice enough. The formality level of a trilby varies according to its design and materials, and a colorful straw version is a lot more casual than the high-end felt one with satin band and feather I wore for my wedding photos. I put trilbies at the very upper edge of casual, but exercise caution with that combination: Therein danger lies.

The trickiest hats are top hats and classic fedoras. Top hats are pretty much strictly relegated to costumery, because they’re so over-the-top and dated. Fedoras are perhaps the hardest of all to pull off, because they carry so much Hollywood baggage; you have to be pretty awesome to wear one and not look like you’re trying to be Indiana Jones or Don Draper and failing miserably. Certainly I am not brave enough to try it.

This has been a small, pointless public service announcement.

9 thoughts on “How to wear a hat

  1. I have a short brimmed black fedora that I wear sometimes, usually when the weather is inclement and I have a nice jacket on. I’m not sure I fit the awesome bill sufficiently enough to actually be pulling it off, but I like it so I don’t mind too much.

  2. Last spring I got a trillby and decided it worked for me, but this winter I got a couple of flat caps to match my jacket and coat and haven’t looked back. I’m wondering what to do when it gets to be too warm for coats! I might have to buy some vests!

  3. Your fashion posts always make me think of this song:

    Incidentally, they are also wearing hats.

  4. Since I own both a top hat and a fedora, it’s fortunate that I spend a good amount of my time at conventions more or less in costume. I’m usually sensible enough to leave them off if I’m not. Pretty sure I don’t actually own nice enough close to pull either off as played-straight formal wear.

    For just keeping the sun off, I have a Panama-style wide brim hat. And then I have a beret, which is always a little goofy, but at least not overly formal. (I do not, however, wear it with a scarf, affected glasses, and an air of disdain.)

    I may consider picking up a trilby someday for more options, since as my hair thins I really need to be wearing hats outside. But I don’t actually have much call for “Business” dress in my life right now.

  5. I’ve passed this along to my university chums. Hopefully this will prevent further instances of triblies plus band t-shirts.

    I tend to dress up naturally. I can’t remember the last time I wore a t-shirt in public.

  6. I went to a school when I was younger that forced us to wear straw boaters, as part of the uniform. As much as I hated it then, I kind of miss it now – I wish I was bohemian enough to pull something like that off, but my personal style is probably just a little too clean cut for them. I’m never without a collar, and I think a boater needs to be pretty dressed down, lest I look like a wannabe vaudevillian.

    Actually this all brings me to another point! I have a large (8″+) head, which makes headwear difficult for me indeed. I think that my only options are short brimmed, such as boaters and pork pies, though I’d love to be proven wrong.

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