How Much Hat Is Too Much Hat?

Monica Ainley is a Who What Wear UK editor-in-residence and a Paris-based fashion and culture writer and broadcaster. She is the co-creator of the influential Fashion: No Filter podcast and the culture podcast Fanfare. Monica also authors Mon Review, a weekly dispatch on aesthetics, literature and contemporary rituals.

Apparently, you are either a hat person or you aren’t. Sure, you might have been told you have a “hat face”, but I find that somewhat subjective. To my mind, it’s more about whether you have a hat personality. I am a hat person. I love a hat, and have rarely regretted any. They are, as far as I can tell, the only good thing about bad weather. And funerals.

Now, as the wind and rain descend upon us (and there happens to be so many good hats on the market), I ask you: why wear a sad waterproof hood when you could wear a splendid hat and look like a timeless movie character? There is something about putting on a hat that instantly makes life feel more interesting. You are no longer simply a woman walking to the supermarket in the rain. You are a woman with a mysterious past, a complicated love life and possibly a train to catch. One need only look at all the references to fabulous hats in literature to understand their power.

F. Scott Fitzgerald opens The Great Gatsby with the immortal instruction, “Then wear the gold hat, if that will move her … till she cry ‘Lover, gold-hatted, high-bouncing lover, I must have you!'”—a suggestion that a sufficiently fabulous hat might be all that’s required to inspire a great romantic passion, and this is a theory I am more than willing to put to the test.

Then there’s the green bowler hat in Evelyn Waugh’s Vile Bodies, an accessory so wonderfully absurd it seems to sum up the entire spirit of the “bright young things”; a reminder that hats have long been associated with people who are having significantly more fun than everyone else. And of course, The Cat in the Hat—arguably the most compelling literary hat experience of all. Would he have been remotely interesting without his hat? I think not. He would have just been a cat. ​

Still, once you are a card-carrying member of the hat lifestyle, you have to realise things can get out of control rather quickly. One minute, you’re indulging in a totally wearable Michael-Rider-for-Celine urban hat fantasy, and the next you’re out there looking like a raging mad duchess who has hit the damson gin too hard and lost her horse.

My brother and I are engaged in a years-long argument about the baker boy cap. You know the one: part train conductor, part Left Bank intellectual, part Karl-era Chanel girl on her way to lunch. A slightly puffed-up cap with a little beak, beloved by stylish women for decades and absolutely intolerable to my brother, who maintains that such headgear is categorically unacceptable. No exceptions. No appeals. I understand his point, because there is something inherently costume-y about the baker boy cap. You are, after all, choosing to dress like a person who might announce the departure of the 10:42 to Marseilles. So how much is too much hat? And which hats are appropriate for which occasion?

Here are my laws of millinery, according to, well, um, me. (And The Cat.) It’s almost like a confidence scale, in that the further you go, the less the hat is about keeping your head warm and/or dry, and the more it becomes a declaration of who you are, or at least who you intend to be that afternoon.

The Gateway Hat

Style Notes: This is where it all begins. A perfectly reasonable hat. A sensible hat, even. The sort of hat that nobody could possibly object to because, well, have you been outside today? Functional, yes, but also an enticing way of adding a little timeless elegance and personality to your winter look when it’s genuinely freezing. Think Anna Karenina arriving at a snowy railway station, all fur and romance and impending emotional catastrophe. Or Julie Christie in Doctor Zhivago. These hats are for women for whom winter is not merely a meteorological inconvenience but an opportunity for a truly excellent silhouette. The great thing about this category, basically, is that you can pretend you are wearing the hat out of necessity, when in fact, you’ve been looking forward to breaking it out since August. This is also a good entry point for the hat-curious.

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2. The “I HAVE A PERSONALITY!” Hat

Style Notes: Now we’re getting somewhere. This is a hat that is not strictly necessary. Yes, it may provide some protection from the elements, but we all know that’s not really why you’re wearing it. You’re wearing it because you think it looks fabulous. And you are correct!! I would still wear this type of hat to any occasion with the right simple and elegant coat, be it Sunday lunch with my in-laws, a mums’ gathering or a fashion show in the rain, as I have on numerous occasions.

The secret here is to let the hat do the talking. A beautifully cut coat, a pair of jeans, some good boots and then bam: hat! An outfit that might otherwise have been perfectly unremarkable suddenly has a point of view. Just don’t count on people not noticing it and asking about it. This is not a hat for disappearing into the background, so don’t wear it if you’re trying to avoid someone.

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3. The Fashun Hat

Style Notes: Ah, we’ve arrived. This is where things can get controversial. This will freak out style-code-loving Parisians no end, but there is something very tasty about this look de temps en temps. It’s a hat that says, “Look at me. I am wearing this hat with enthusiasm, nay, vigour. I am the kind of person who would wear this hat, and now I am. I don’t care what you think of me because I think I look like The Main Character. I am indeed shielded from the elements by my hat, and from your mockery by my iron-clad self-confidence and comprehensive fashion understanding. Muahaha! Clear away, my good people!”

There is something quite liberating about this level of commitment. Once you have decided to wear a truly enormous hat in public and pulled it off, you have truly freed yourself from the tyranny of other people’s opinions without shrinking away—quite the opposite. Of course, there are practical considerations. You may not be able to sit in the back of a car. You may obscure the people behind you. You may find yourself unexpectedly airborne in a strong gust. But these are sacrifices that I am willing to make.

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So, how much hat is too much hat? The answer: exactly as much as you can carry off. Not physically, though that is a factor, but psychologically. A hat demands commitment. You can’t go in half-heartedly or pretend you accidentally put on a giant wide-brim or a baker boy. You have to own it, which is precisely what makes hats so divisive. They announce that the wearer is having a lot of fun getting dressed and is prepared to be noticed doing it. And isn’t this precisely what fashion should be about?