President John F Kennedy (aka Hatless Jack) is said to have been responsible for the decline in the popularity of men’s hats. For years, we habitually wore them as unthinkingly as we now wear coats, shoes and shirts, and yet these days many men regard them as too hard to pull off. So how do the others do it? As street-style pin-ups Messrs Sam Lambert and Shaka Maidoh so ably demonstrate above, it’s all down to familiarity. So, once you find a hat you like, hang it by the door and put it on whenever you leave the house.

Finding the right summer hat needn’t be difficult, it just requires a little thought. Style, as ever, requires a man to blend his taste with an objective view of what suits him – a tall man with a big head should look at wide-brimmed hats, such as fedoras or Panama hats, just as a short guy with a thin face may find it easier to wear a hat with a narrow brim. Traditional caps are no different, because a full eight-piece baker boy cap will create a very different effect to a neat summer flat cap.

As for how and when to wear them, the good news is that we’ve never been freer to wear what we like, when we like, which means that when it comes to summer hats for men, it’s open season. Want to pair a taupe fedora with faded workwear? Go for it. A finely woven Panama hat with a navy blue suit? Knock yourself out. There’s only one piece of etiquette that remains relevant, which is that a man should remove his hat when he’s inside. The trick is to remember it again on the way out.

It’s hard to avoid the suspicion that the Ecuadorian hat industry missed a trick when it allowed its finely woven straw hats to become known as Panamas. But how to work one of these classic men’s summer hats into an outfit? Look and learn. There are more blues in the shot above than there are on an album by Mr BB King. But vitally, these white Panama hats are brought smoothly into the mix thanks to their blue bands, which work much better than black ones (brown bands are another welcome variation). Both men are dressed in very modern interpretations of smart casual, thanks to the mix of soft tailoring, spread-collar shirts, faded denim, jewellery and sunglasses; the Panama hats lend an air of sophistication and elegance. By the way, if you have never worn a Panama hat before, you will be pleasantly surprised by its ability to keep your head cool while protecting you from the sun.

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A faded, logo-free summer cap is an important element in the wardrobes of men in thrall to vintage workwear. In this case, it’s being worn with an artfully distressed, beautifully made hickory-striped chore jacket – note the chunky burnished-metal buttons and the raglan sleeves. It’s stylishly worn buttoned at the neck, falling open to reveal the white shirt beneath. The cap itself looks like those worn by US airmen in WWII and it visually reinforces the coat’s blue colour, while metaphorically reinforcing the coat’s blue-collar origins. However, this is ideal weekend-wear regardless of a man’s profession.

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The fedora is a remarkably versatile hat. For a long time it was only associated with a certain kind of dandyish Englishman, but it has now been liberated as a casual accessory, something for which Mr Pharrell Williams probably deserves some thanks. Felt hats are robust, and their history has more to do with pioneers in the outdoors than it does with flâneurs in the city. In this photograph, both men are in what appears to be the most elevated form of artisanal Japanese workwear, with an intricate collage of patches on our right, and an unusual kimono-style jacket on our left.

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The snapback baseball cap – so named because of the adjustable strap on the back, with a wide brim and an association now closer to basketball than its baseball origins – is a blank canvas, worn by everyone from rich, old, white presidential candidates to the latest hip-hop star to the guy next door. In this case the snapback baseball cap is being deployed as part of an outfit that’s winningly simple, but still fashion-aware. The virtues of the less-is-more approach can hardly be more neatly expressed than by pairing dark jeans with a loose-fitting white T-shirt. The cap’s subdued pattern is noticeable enough to provide some visual depth, without diluting the pared-down palette.

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For a masterclass in wearing a flat cap, look to the BBC gangster series Peaky Blinders. The British show is set in Birmingham’s criminal underworld in the years following the Great War, and the antiheroes are walking adverts for the tweed cap – to the extent that the flat cap is now known as the “Peaky Blinders cap”. But how does a man wear a flat linen cap in summer without looking like a pétanque-playing French pensioner? By looking like an artist instead. Ensure that one’s radical credentials are beyond doubt by spending a lot of time at the tattoo parlour. Then, wear some hard-to-place pleated black trousers with an attitude that can only be described as Gallic. It’s an unusual look that’s defiantly contemporary, even though it’s assembled from a series of classic elements. We’re betting that there’s at least one book by Mr Jean-Paul Sartre in that backpack.

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Anyone who lived through the Madchester era of the late 1980s and early 1990s will forever associate the bucket hat with the laddish fashion of Messrs Liam Gallagher, Ian Brown, Richard Ashcroft et al, but there’s much more to this soft-brimmed hat than just that. Take, for instance, the gentleman pictured here, whose khaki-coloured hat offers a casual contrast against the buttoned-up military rigour of his army-green shirt. In terms of formality, the bucket hat occupies a sweet spot between the laid-back sportiness of a baseball cap and the gentlemanly elegance of a Panama hat, and this versatility makes it an appropriate choice for a wide variety of summer outfits. 

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