’s Ultimate Accessory—From Gateway Beanies to Full-Blown Fashion Statements**
By Monica Ainley
There is an old adage that suggests you are either a hat person or you aren’t. While some might claim you need a specific "hat face," that notion feels rather subjective. To my mind, whether you pull off headwear successfully is less about facial geometry and more about whether you possess a hat personality. I am firmly a hat person. I love a hat, and I have rarely regretted wearing one. In fact, hats are, as far as I can tell, the only genuinely good thing about bad weather, or funerals.
Now, as the wind and rain descend upon us—and with an abundance of exceptional millinery currently on the market—it is worth asking: why wear a sad, anonymous waterproof hood when you could wear a splendid hat and look like a timeless cinematic character? There is an undeniable alchemy to putting on a hat; it instantly makes everyday life feel more interesting. You are no longer simply a person walking to the supermarket in a downpour. You are suddenly an individual with a mysterious past, a complicated love life, and quite possibly a train to catch. One need only look to literature to understand the profound narrative power of a great hat.
F. Scott Fitzgerald famously opened 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 is required to inspire great romantic passion, a theory I am more than willing to put to the test. Then there is the green bowler hat in Evelyn Waugh’s Vile Bodies, an accessory so wonderfully absurd it seems to encapsulate the entire spirit of the "bright young things," serving as a permanent reminder that hats have long been associated with people who are having significantly more fun than everyone else. And, of course, there is The Cat in the Hat, arguably the most compelling literary hat experience of all. Would he have been remotely interesting without his signature stovepipe? I think not. He would have simply been a cat.
Still, once you cross the threshold into the hat lifestyle, things can get out of control rather quickly. One minute, you are indulging in a thoroughly wearable Michael Rider-for-Celine urban hat fantasy, and the next you are walking down the street looking like a raging duchess who has hit the damson gin a touch too hard and lost her horse.
My brother and I have been engaged in a years-long debate regarding the merits of the baker boy cap. You know the style well: part train conductor, part Left Bank intellectual, part Karl-era Chanel girl on her way to an exclusive lunch. It is a slightly puffed-up cap with a short beak, beloved by stylish women for decades, yet found utterly intolerable by my brother, who maintains that such headgear is categorically unacceptable with no exceptions and no appeals. I can understand his perspective, because there is something inherently costume-y about the baker boy cap. You are, after all, consciously choosing to dress like a person who might stride onto a platform to announce the departure of the 10:42 to Marseilles. This naturally raises the eternal question: how much is too much hat, and which styles are truly appropriate for specific occasions?
The Gateway Hat
This is where the journey truly begins. A gateway hat is a perfectly reasonable, even sensible piece of headwear. It is the sort of hat that nobody could possibly object to because, quite frankly, have you looked outside today? It is functional, yes, but it is also an enticing way of adding timeless elegance and personality to your winter wardrobe when the temperature plummets.
Think of Anna Karenina arriving at a snowy railway station, wrapped in fur and romance amidst impending emotional catastrophe, or Julie Christie in Doctor Zhivago. These hats are designed for individuals for whom winter is not merely a meteorological inconvenience, but rather an opportunity to showcase a striking silhouette. The great advantage of this category is that you can pretend you are wearing the hat entirely out of raw necessity, when in reality you have been eagerly anticipating the first frost since August. It also serves as the ideal entry point for the hat-curious.
The "I Have a Personality!" Hat
Moving further along the spectrum, we arrive at the territory of the "I Have a Personality!" hat. Now things are getting interesting. This is a hat that is not strictly necessary for survival. Yes, it may offer some nominal protection from the elements, but we all know that is not the primary reason you chose to wear it. You are wearing it because you know it looks fabulous—and you are entirely correct. I would comfortably wear this style of hat to almost any daytime occasion when paired with a simple, elegant coat, whether that means Sunday lunch with the in-laws, a school gate gathering, or standing in the rain outside a fashion show, as I have done on numerous occasions.
The secret to pulling off this look is to let the hat do the talking. Pair it with a beautifully cut coat, a classic pair of jeans, and some sturdy boots, and suddenly an otherwise unremarkable outfit is elevated by a clear point of view. Just do not expect people to ignore it; this is not an accessory designed for blending into the background, so it is best avoided if you are trying to remain unnoticed.
The Fashun Hat
Finally, we arrive at the summit of millinery commitment: the Fashun Hat. This is where things can become genuinely controversial. It may freak out style-code-loving traditionalists no end, but there is something deeply satisfying about embracing this look from time to time. This is a hat that proudly announces, "Look at me. I am wearing this hat with enthusiasm, nay, vigour."
It is worn by someone who thinks they look like the main character and is entirely unbothered by outside opinions, shielded from both the elements and potential mockery by iron-clad self-confidence and a comprehensive understanding of fashion. Once you decide to wear a truly enormous or avant-garde hat in public and successfully pull it off, you have liberated yourself from the tyranny of other people’s opinions.
Naturally, there are practical compromises to consider. You may find yourself unable to sit comfortably in the back of a car, your brim might temporarily obscure the view of the person sitting directly behind you, or you may even find yourself unexpectedly airborne during a strong gust of wind. But these are minor sacrifices for the sartorial rewards on offer.
Ultimately, the question of how much hat is too much hat comes down to a matter of psychological capacity. A hat demands absolute commitment. You cannot approach it half-heartedly or pretend that you accidentally slipped into a giant wide-brim or a baker boy cap. You have to truly own it, which is precisely why hats remain so deliciously divisive. They broadcast to the world that the wearer is having a wonderful time getting dressed and is fully prepared to be noticed while doing it—and isn’t that precisely what fashion should be about?
