You Should Know How to Do This: Wear a Hat

There’s no reason to be modest about this: I look spectacular in a hat.

I mean, COME. ON.
This is a 7 a.m. car selfie, even. This is the power of the right hat.

Hats occupy the uncanny valley of clothes: they have all the aspects of things one might put on one’s body (softish, cover something up, come in sizes), but a vast segment of the population feels somewhere between uneasy about and repulsed by the idea of actually integrating them into their lives.  Whenever I venture out of the house wearing a hat, someone says, “I love your outfit! I wish I could pull that off!”

I bought this last week when I had a bad day.
I bought this last week when I had a bad day.

Can I tell you a secret? There’s no such thing as “pulling it off.” You don’t have to have amazing bone structure or a certain haircut or be between 18-22 or anything at all. The reason you think I look good in a hat is that it’s novel (if you don’t know me) or you’re used to seeing me in one (if you do).

When I was 15, I was at Dot Fox, talking to my style mentor Sally Bird (I know we’ve talked about Sally), and admiring this big, black felt hat. Since I was 15, I said something like, “I love this but I couldn’t ever wear it! I’d feel so silly about how weird I’d look because I am a teenager and think everyone is looking at me all the time and actually no one cares but I think they do.”

Sally said this: “You know what the trick to pulling it off is? You put that sucker on and don’t take it off until everyone is telling you how goddamn stunning you are.”

I have applied this particular piece of advice to virtually every aspect of my life, and it has seen me through the period where I wore a lot of really brightly patterned pants and hoop earrings, that time when I dressed like some Seth Cohen dream girl and owned only Converse and obscure band t-shirts, and the Winter of the Black Dresses, which we don’t need to discuss. Unfortunately, I have also applied Sally’s sage words to non-sartorial decisions, which led to some questionable romantic and professional outcomes, but that’s another story for another time. The point is, even when I was wearing a skirt made out of neckties with an appliqued sweatshirt and these carved glass clogs, people were telling me how great I looked because I didn’t ask them to tell me how I looked. At this point, you’re already armed with my most important piece of hat advice: Put it on. Don’t apologize.

We can talk about my wigs later, but yes, I wear this top hat Out Places without a shred of apology in attendance.
We can talk about my wigs later, but yes, I wear this top hat Out Places without a shred of apology in attendance.

Now, there are some steps you can take to look objectively good, and not just good because you are confident. A unisex piece of advice before we get started in earnest: when you go to the shop to start looking, you’re initially going to think that you look horrible in all hats. That’s because you’re not used to what you look like in hats, and they change your face and outfit immeasurably. Try on a ton. Ask the attendant. Take some pictures and text them to your friend/mom/stylist. You probably look great, since you have a head and that’s the only barrier for entry.

The other thing is to remember that men need to take their hats off indoors, and women should keep them on if they’re part of the outfit. I didn’t make the rules, but it’s going to really suck when a member of the Greatest Generation approaches you and tells you off, so you should just go ahead and follow their lead.

Let’s start with men, since I think they need to proceed with caution on this one, and because I love a man in a hat and am trying to spread the good word. I take a man in a hat much, much more seriously than a man who does not wear a hat.

I want to make sure you can here me, dudes. Can you? Is this thing on? Are you all listening? Unless you’re really sure of what you’re doing (like, “I can readily distinguish between a trilby and a fedora to the satisfaction of a milliner”-sure, not “I once wore colored chinos out to a tailgate and that one girl said she liked them”-sure), do not buy a fedora and then wear it with jeans and a blazer out places. I’m sorry, but The Situation and Pick Up Artists and Mad Men Cosplayers ruined this for everyone. It’s not fair, I know. It isn’t. But the world isn’t fair, as my access to healthcare and and right to control outcomes for my body will tell you. This is just your cross to bear, and I expect you to do so with the grace and dignity we have come to know and expect. That said, if you look good in a fedora and you’re really sure you look good, buy it in not-black and get down with your positively unfunereal bad self.

My best friend is a man who favors a cap. When we were teenagers, he festooned his everyday cap with band patches, but has come around to a less exuberant form of expression in his latter years. I cannot find a picture of him wearing it that he wouldn’t kill me for resubmitting to the internet, so you have to believe me. He is a very tall, thin man, and it lends him a certain seriousness (he is already serious, but still). This is a good, entry-level hat, and has the desired effect of not making you seem like you’re Trying So Hard, but that you did mean to leave the house. It looks good on almost everyone, isn’t expensive, and is easy to size. Get one in a subdued gray or brown plaid, and wear it this autumn and winter. You can’t really mess up and look bad in a flat cap unless you buy the wrong size or an ugly one.

The other low-risk hat I think the menfolk should try out is a Panama hat for the spring and summer. It somehow seems appropriate in most settings. As a general rule, remember that a bigger face/bigger guy is going to look better in a wider brim and the narrower brims look better on smaller faces/smaller dudes. You don’t want it to look like a toy, but you also want to avoid the kid-wearing-dad’s-clothes vibe. Keep in mind that the white-with-black-brim can be quite formal, so think battered linen, not madras and boat shoes, to keep yourself from seeming prim.

If you’re feeling more adventurous, by all means, get yourself a Stetson or a beret, but know that you’re into uncharted waters. I know guys who favor both of these styles and look fetching, but they are very, very certain kinds of men. You have to be comfortable being called “hoss” (former) or “Che” (latter), and you have to be sure you aren’t wearing a costume. There is nothing less compelling than a costumey dresser. In either event, go for something more subdued– a Stetson with a lower profile to avoid the Man in the Yellow Hat thing, a beret in not-green– and double check yourself on the way out the door.

If hats become your thing, the Art of Manliness has a pretty decent guide to the more nuanced aspects of how to look good in a hat, and some other options (porkpies! bowlers!), but I thought it might overwhelm you.

Now, ladies, you have a lot of options. All the options. You are less likely to look like a cartoon, and that’s really great. Yay! As a person who dresses kind of like a cartoon, though, I am here to tell you it’s great fun, so maybe think about it.


The only proceed-with-caution hats for you, Miss Lady, are absurd ones (top hats) or colors you know not to look that great on you (for me, that’s pastels and most things on the orange spectrum). Other than that, you can do whatever.

A good way to think about your eventual hat is to consider your face shape. Face shape, to me, is kind of like phrenology (which is to say, Not A Thing), but if you feel like your face is round, then it is round, etc. Round faced girls are going to want to avoid a rounded crown (you’ll think you look like an egg, even if you don’t) and stick to sharper angles. Those really sculptural hats can be your friend, as can a pointier fedora (click with caution, it’s so coveted). You can also cock your hat to the side or up or to whatever angle you please– you’re symmetrical, so do whatever.

If you’re someone who feels like she has sharp angles to her face, you’re first steps out of the gate shouldn’t be a big fascinator or a sharp-edged Panama hat. Try a cloche, try a floppy brim, try whatever sloped, gentle shape you see. You’ll feel softer and that will help you feel like you look good in hats. I am past the “which hat do I look good in” phase of this and just do whatever I want, but I am self-conscious about my strong jaw and sharp nose, so my first forays in the haberdasher resulted in my early hat wardrobe being dominated by these shapes.

The beanie and the beret: indispensable baby steps.
The beanie and the beret: indispensable baby steps.

Unlike outcomes for a lot of men, a beret isn’t necessarily a costume for you, and a pillbox doesn’t have to look hopelessly retro. Do you, and remember to just keep the hat on until compliments are flowing like milk and honey in the Promised Land of the Stylish.

So, have I inspired you to buy a hat? If you’re a hat-wearer, will you PLEASE send me pics of you wearing hats as well as the address of your favorite hat shops? I’m not kidding. At all. Happy hatting!

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