5 hat wearing tips from Humphrey Bogart’s hat maker (or 'How I Learned to Stop Worrying and Love the Fedora')

I sometimes look at film stars from yesteryear and feel so inadequate. The smooth way they glide around the screen, with a nod or a flick of the hat, before wandering on to the next adventure, glibly delivering killer lines to whoever needed to be taken down a peg or two.

So when I was invited down to the London boutique of Borsalino, the makers of Humphrey Bogart’s iconic hat from Casablanca (so famous that the company now has its own range of Bogart fedoras) my feelings of dread are two-fold:

Firstly, after watching the new documentary into his life, Humphrey Bogart: Life Comes In Flashes, I realise just how far I am from ever being able to evoke his effortless cool. Putting the Hollywood golden-age star under the microscope, through the lens of his relationships, the documentary offers a rare insight into one of the true stars of the silver screen.

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Xan Brookes, writing about the documentary in The Guardian, described Bogart (far better than I ever could) as having a “hard-boiled coating [that] contained an air of refinement…He was American cinema’s fallen angel, its shop-soiled cynic; sometimes drawn to darkness.”

Compare that to me, who recently fought (and paid over the odds) to get Girls Aloud tickets and once fell over at a bus stop trying to see if my backpack was open, and I feel I’m not going to suit the same hat style as he.

In fact, the only thing I suspect we’d have in common is neither of us have ever been referred to as ‘traditionally handsome’.

The second reason I’m worried: I do not look good in hats. Never have, and have a strong suspicion I never will.

I can’t tell you why - it’s just, over time and through ‘looks’ from other people, I just don’t feel right whenever I’ve put something on top of my hair.

So the thought of having to go through the experience with a company that has decades of experience adding fancy felt flourishes to people’s heads is not something I’m looking forward to.

Expert help

As I enter, I meet Marco and Imane, the people running the London branch of Borsalino, two people who I can instantly tell are far more stylish than I’ll ever be.

And yet, somehow, within minutes I’m unloading my worries about the shape of my head to them like they’re some sort of head-focused therapists - and it’s actually making me feel like there’s hope.

Marco firmly tells me anyone can wear a hat (which, on reflection, isn’t surprising given it’s his profession to sell them), but is certain that it’s just a matter of going through the options to find what works for me.

And so, we do. I’m taken through colours, brims, construction, materials and fit - and Marco makes every effort to hear what I want and how he thinks we can achieve it.

I start to get a little over-excited at one point, asking to try on an electric blue number, and this is where we can see the value of having an expert helping out. Marco is great at letting me try all the options, then kindly, but firmly, hinting what he thinks might work (which turns out to be a more understated, dark blue fedora).

Well, if this is to be the birth of my ‘person that wears hats’ era, I figure I’m going to need to learn how to embrace this lifestyle.

So, during the fitting, I talk to Marco and Imane about the things they’ve learned through selling hundreds of hats, and they have a very clear view on some of the things you should think about if you want to join me on this head-warming journey.

How to wear a hat — and not feel like an idiot

1. Find a hat that fits your attitude

When I entered the Borsalino shop in London’s Burlington Arcade, I’d already walked past a number of high-end retailers selling things I didn’t know how to buy (including a glove shop so fancy that it, somehow, instantly made my hands themselves feel as if they’d been picked out from the bargain bin).

So on entering the milliners, I just had no idea what kind of hat I was ‘supposed’ to have. But it turns out, it’s the one that makes me feel the most comfortable. While I loved the idea of walking out wearing a cheeky electric blue hat, it wasn’t something that felt like it fitted my style - going for something dark blue, with a medium brim, felt less ‘risky’.

The point to this being: a hat is the same as any item of clothing, where if you don’t feel like you can wear it with joy, then it won’t be the right one for you.

2. Always go for a larger size

If you’re not being fitted for a hat, knowing how to find the right one (especially as a new hat buyer) feels rather daunting.

The rule of thumb is that a good-quality hat will never expand, only shrink, so it’s best to go for a size slightly larger and get some felt inserts to find the perfect fit for you.

Marco tells me the hat should never touch the sides of your head between your temples and ears, so find something that slots into that spot.

3. Take it off with your whole hand

I’d watched Bogart remove his hat multiple times during the documentary, but there was no way I could explain how he does it with both impunity and softness.

Thankfully, Marco was on the case, explaining that the right way to do it is to clasp the front gently between thumb and forefinger… but never pinching hard.

“Then, with three fingers in between, you grab your hat very gently, not putting a lot of pressure [on the top],” he says.

This action creates the well-known teardrop shape on the top of the fedora. This pinch was actually born from Giuseppe Borsalino (the founder of the hat sellers), and Marco says “The pinch [has become] a statement, but it was [created] just to make it easier to grab and remove the hat.”

4. Keep it straight

In my bid to not look like a proper newbie hat wearer, I did some research on how to wear a fedora, but it turns out I needn’t have bothered.

Where I thought a slightly rakish angle was the right way to go about things, it turns out that the classic look is far simpler:

“The proper rule is to wear it straight,” says Marco. “There are a lot of people who are more creative who twist, they wear it differently, it’s just how you feel.

“But for the classic look, the rule is to wear it straight, especially if you’re going back to the age where all the men were wearing a suit.”

5. You wear the hat, the hat doesn’t wear you

This was the hardest point for me - and one that Imane had to really coach me through. I opened up to her that I just felt foolish wearing a hat, that people would be ‘looking’ at me.

She advised me to put the hat on and then just observe myself in the mirror for an uncomfortably long time.

“Keep looking, because you’re going to get used to it,” she said. “You might think ‘I don’t like it, but I like the idea’. Then after 10 minutes, maybe 20 minutes, you start to think ‘actually, I like it. You know, it’s not bad?’”

So I do it, and it’s as deeply uncomfortable as I expect it to be. I’m just looking at myself wearing a hat, wishing it didn’t look so odd.

But after a little while, I start to get a sense of longing. I want to be part of a world where a hat was expected, that taking it off meant something, whether that’s leaving the outside world to the comfort of my home or just a kinder way of saying hello.

I wanted to be like my grandfather, who I can imagine passing it off with effortless nonchalance. I want to be able to touch the brim like Bogart and make some sort of clever, non-verbal point that a lifetime of my terrible jokes could never recreate.

So maybe I will - or maybe I’ll just crack it out when I’m wearing my fanciest suit and want to add a stylish touch to proceedings.

The thing I take away from the experience is actually quite overwhelming - that it’s OK to want to try something different, and forcing yourself through the discomfort of facing up to that can lead to experiences you’d never expected.

Am I now a hat person? It’s hard to say… but I’m far less worried about covering my head than I used to be, and if I can ever muster a flicker of the cool nonchalance of Bogart in the years to come, that’ll feel like a massive success.

Lead image: Photo by Donaldson Collection/Michael Ochs Archives/Getty Images
All other images courtesy of Borsalino

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