10 pieces of headwear every man should own in their lifetime

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Jamie Carson
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They’re there to save the day when you’re hungover and can’t be bothered doing your hair, when it’s raining and when you start to go bald, hats truly are little miracles.

But when it comes to branching out from the archetypal baseball cap, men can be a little reluctant, fearing that they may look like Heisenberg if they wear a pork pie hat. So we’re here to help you on your journey into experimenting with different headwear…

Image source: Rex/ Getty

  • Military cap

    It’s got Beckham’s approval, so you really shouldn’t need any more convincing than that. If you’re sick and tired of your everyday baseball cap, this Ben Sherman hat is the logical step up as it doesn’t stray too far from it, but alters the shape just enough to make a point.

    Score one yourself

  • Pork pie hat

    Enough time has passed since Breaking Bad to wear these without having “I am the one who knocks!” shouted at you in the street. Reclaim the look and wear it as the early 2000s indie staple it was meant to be.

    Get the look

  • Fisherman beanie

    Not just for fisherman, as you will clearly see in East London when a fixie bike speeds past you. If your ears get irritated with the average beanie, cut off a few inches with this style and give them the fresh air they need.

    Catch one now

  • Fedora hat

    You don't have to be into organised crime in the Fifties or be of Italian descent to pull off a fedora, as it's become a modern headwear staple that can be worn in both smart and casual ways.

    Use your head

  • Baker boy hat

    In no way are we suggesting that you sew razorblades into your cap like the Peaky Blinders - all we're saying is this is a fantastic show to get your vintage headwear inspiration from. So please don’t sue.

    Get yours now

  • Panama hat

    Panamas are part of the smart headwear family. So if you’re at a summer wedding, this is an acceptable piece to wear with a linen suit. But make sure you take it off when you sit down, you don’t want to spoil any pictures with your massive head.

    Get ahead-wear of the game

  • Trilby hat

    When you say trilby, you think of a smacked out Pete Doherty or maybe some guy in his late twenties playing World of Warcraft in his basement, but it really is so much cooler than that, as Frank Sinatra proves as he lays down some vocals (note to millenials: that's what artists used to do before they dropped beats in their bedrooms).

    Do it Frank's way

  • Straw hat

    Your holiday cannot possibly start without wearing a straw hat. This is almost as important as, if not more than, your passport. But make sure it’s supported in its upright position in your suitcase, because nothing ruins a trip quite like a crushed hat.

    Start your holiday

  • Cowboy hat

    This is a style you should wear when you get to a grand old age where you can tell people what you really think of them without any repercussions. Best worn sat at a Los Angeles bar supping neat bourbon.

    Get your Motorheadwear

  • Russian winter hat

    In Soviet Russia, hat wears you! If your flat is freezing in the winter, then this is a warm and comfy hat to fall asleep in. It’s been tried and tested by us, we’ve lived in some rotten places.

    Join the (Communist) party


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Jamie Carson

Jamie Carson

When he’s not pretending to be on the front of an album cover, Online Style Writer Jamie Carson can probably be found criticising your fashion credentials. Follow Jamie on Twitter @_jamie89

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