In an interview way back when, Liam Gallagher was asked whether trainers or a jacket were the most important part of an outfit. I can’t quite remember his answer, but whatever it was – it wasn’t the right one. The most important part of an outfit is a hat.
What you wear on top of your dome completely changes the way everything beneath it is perceived. A baseball cap instantly turns up the Americana-ness. A foldless beanie evokes imagery of the late-’90s. And anything with earflaps will have people thinking you’re either a hill walker or a washed-up Hacienda head.
Headwear sets the tone. And for something that takes up so little space, the self-expression-to-size ratio is about as impressive as it gets. With that said, it’s easy to get addicted to headwear. Hunting for the perfectly shaped cap is a never-ending pursuit I know all too well – my collection of headwear on top of my wardrobe has been steadily growing over the last five years like a wearable tumour. Before joining Proper, I spent all day looking at caps. After joining Proper, I still spend all day looking at caps – only now I’m paid to do it.
So here are 15 of my favourite pieces of headwear on the market right now – some I own, some I want to own, and some I’m desperately trying not to press purchase on.

Big Rock Candy Mountaineering Truckin’ Grizzly Cap
I’ve always loved Big Rock Candy Mountaineering’s headwear offering – they absolutely nail that late-’80s shape – and this grizzly bear cap is a perfect case in point. The colours are great, the bear is cool, and it somehow only retails for £29. Which is why it’s now sitting in my cart.
Khakis is my favourite brand on the planet right now – and that’s probably got something to do with their delectable headwear. This Mark 6P Cap is the pick of the bunch from the current lineup, appearing in a shade of green I’m fairly sure I last saw in Primary School.


Don’t be fooled by the bucket hat’s simple appearance – from my experience, they’re about as complicated as headwear gets. Finding the fit right is essential if you want to avoid drifting into bad Oasis tribute territory, and this Burlap Outfitters Sailor Hat lands firmly on the right side of it. Much more Serpico than Slide Away.
Cafe Mountain Music and Arts Cap
As mentioned earlier, few things deliver quite as much self-expression per square inch as headwear – and this Café Mountain cap makes the case perfectly. Ideal if your perfect Sunday involves hiking to a jazz café on top of a mountain while doing a landscape painting.


The North Face Purple Label Ripstop Field Cap
The sort of cap you’d see a bellboy (do bellboys still exist?) wearing when checking in at a really cool Japanese hotel.
@presta94 posts a load of cool old mountain bike pictures, and makes some very tasteful headwear. This incredibly ’90s design is predictably sold out at the moment, but rumoured to be re-released soon.


However you spend your Saturday – fifteen pints and every Premier League kick-off, or fifteen kilometres followed by an ice bath – this Saturday Project cap is up to the job. Cut from a sturdy ripstop fabric, it’s built to handle the odd knock, too.
Every time I spend a morning commute with a wet head (which is unfathomably often), I start thinking about this Snow Peak GORE-TEX Bucket hat. Should probably just buy one already, to be honest.

In the ever-growing pile of headwear perched above my wardrobe, this Montbell cap is the one I reach for time and time again. I’ve worn it to death, and my only complaint is that they haven’t produced it in every colour under the sun.


Another piece of Montbell headwear that’s been on my wishlist for way too long. Although the only real similarity to the one above is the logo – beyond that, it’s considerably less watertight, an entirely different shape, a different colour, and, in fact, a completely different genre of hat altogether.
Usually, you’d associate Barbour with heavyweight waxed apparel, but this Festival Pocket Cap proves they can turn their hand to lightweight gear too. What the image doesn’t show is the pocket on the side panel – which is frustrating, because it’s arguably the best bit.


These Goodlids Splash Soft Brim Caps have been a staple in the Proper office for what feels like forever. And that’s down to their impressive lightweight, packable and wearable properties.
From what I can tell, TDR have taken inspiration from the golden era of Disneyland merchandise for this Team Cap, and the results are fantastic.


