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What hat should I wear?

What hat should I wear?

It wasn’t so long ago that no man would be seen outside without a hat. But since JFK forswore one for his inauguration, what was once a menswear staple has become something more divisive. For every man who wears one all year, there are five who think that no style of hat suits them at all.

“Some hats have a certain level of stigma to them,” says Thread stylist Alexander McCalla. “And the relationship between the hat and outfit can be confusing. Some guys question whether they can wear a certain hat with a suit, or if it will work a relaxed look. So they tend to play it safe and not wear one at all.”

But a well-worn hat can be an easy way to elevate your style. “It can make an otherwise uninspiring outfit look different,” says Alexander. “And unlike a coat or a pair of shoes, it requires little investment.” The best hats work with multiple things in your wardrobe – unless you want to develop a deep collection, it’s best to find a versatile style that fits your personal aesthetic. “Let your wardrobe dictate what type you go for.” Just answer these four questions to find the perfect hat for you.

1. Are you nervous about wearing hats?

Yes – get a beanie

No – go to question 2


The beanie is the simplest hat to wear, because it’s the most functional. “It’s designed to keep you warm,” says Alexander. “So it doesn’t make too much of a statement if you don’t want it to.” That practicality means beanies tend to go with anything from a suit to jeans, provided you stick to dark colours with no bobbles or branding. “It’s the most accessible and looks as good on older guys as it does teenagers.”

Do you feel a bit old for a baseball cap?

Yes – get a baker boy cap

No – go to question 3

Baker boy cap

There’s no real cut-off when something is age inappropriate. But style is about being comfortable in the clothes you wear and if you’re worried baseball caps are too youthful, the baker boy is a more refined option with centuries of heritage. “The materials should reflect your wardrobe,” says Alexander. “Things like denim or canvas are great with workwear, but tweeds or wools are good if you’re a bit smarter.” And because they’re lighter than a beanie, they also work all year round.

3. Do you wear a suit regularly?

Yes – get a trilby or fedora

No – go to 4


This was the smart man's default choice in the 1950s, but they’re now trickier to wear as clothing has grown more casual. “It can be quite a fashiony thing for younger guys, particularly styles with wider brims,” says Alexander. “But if you’re a bit older then it looks really refined with a tailored look. It’s the kind of finishing touch that shows you’ve thought about what you’re wearing.”

4: Get a baseball cap

Baseball cap

As with beanies, the subtler your cap, the better. “No teams or logos,” says Alexander. “And a curved brim is better than a flat peak.” Materials can add interest in a more nuanced way. “Try wool in winter and cotton in summer. It gives your look some really great texture that can lift a look that feels a bit stale.” Stick to casual looks – a baseball cap with a suit is a tough look to pull off. And never, ever be tempted to wear it backwards.