Men are, as a rule, slightly apprehensive when it comes to hats. Partly because it feels like an unnecessary flourish, and partly because we are haunted by the fear of hat hair. But there is a case to be made for a small, curated rotation of weather-appropriate headwear. The types of hat that don’t try too hard, that serve a purpose, and that feel like a natural extension of your capsule wardrobe rather than an embellishment.
The key is choosing hats that are low on ego and high on utility. Hats that make sense in context – a run to the shops, a walk to the pub, a brutal cold snap – and quietly do the job without demanding too much attention. Below, the types of hat every man should own, and why.
Unstructured baseball cap
The cleanest, most wearable cap in the line-up. Lighter and less rigid than its snap-back cousin, the unstructured baseball cap is more art-school than sports team. It’s the kind of hat that doesn’t need a logo to work (though a discreet one won’t hurt), and can be thrown on with everything from tailoring to gym gear. Perfect in summer, but increasingly a year-round staple. Ideal for bad hair days, impromptu coffee runs, and moments when you’d rather not be recognised.
Wool baseball cap
The grown-up sibling of the above. Slightly smarter, often lined, and more appropriate when the temperature drops. It still says ‘weekend’, but in a more put-together way. Think soft tailoring, wool overcoats, maybe even a roll neck if you’re feeling brave. The sort of hat that makes you look like you’ve got your life together, even if you don’t. It’s also a clever halfway house for men who aren’t quite ready for full-on beanie season.
Merino beanie
A beanie, but done properly. Merino is soft, breathable and never itchy. More importantly, it holds its shape – no stretching, no sagging. This is the beanie you wear with a navy overcoat in winter, the one you leave in your bag all autumn, the one you come back to year after year. Ribbed or plain is up to you. Just avoid slouchy styles unless you’re in a band, or currently backpacking through South America.
Fisherman beanie
These types of hat are the polar opposite of the above. Small, cropped, sits above the ears. Not for warmth, then, but definitely for aesthetics. Looks best with a chore jacket, heavy knits, and a general air of coastal nonchalance. Has a whiff of the artisanal about it – coffee roasting, vinyl sorting, sourdough baking – but that’s part of the charm. Popular with baristas and barbers for a reason. Not ideal in sub-zero temperatures, but it earns its keep on cool spring mornings and chilly commutes.
Bucket hat
The most divisive hat on this list. Some men simply refuse to entertain the idea. But that’s a shame, because a bucket hat is a deeply practical, highly wearable piece of kit. Choose a neutral colour, keep it simple, and you’ll be surprised how often you reach for it. Useful in the rain. Brilliant in the sun. Easy to stash in a bag. Unfairly pigeonholed as a ‘festival thing’ or a ‘dad on holiday’ thing – when in fact, it's a solid option when styled with care.
Trapper hat
Not for the faint-hearted. But when it’s really cold – and we mean really cold – only these types of hat will do. Originally designed for hunting, the trapper hat has long since entered the style canon, thanks to its functional silhouette and rugged charm. Fur-lined ear flaps optional, but recommended. Save it for the depths of winter. Looks completely ridiculous indoors, but noble and practical when there’s frost on the ground and your ears are at risk of falling off.
Cuffless beanie
Trending at the moment because of 'that' Arc'teryx beanie, this type of hat is neat, minimal and slightly under-the-radar. Choose one in charcoal, navy or bottle green, and wear it with anything. Especially good for being active outdoors in the winter when you want the warmth without the bulk. It’s the sort of thing you’ll wear without thinking – which, really, is the mark of a good hat.
Next up: The best light jackets to beat the transitional weather.
