The baseball cap has long been one of menswear’s most polarising accessories and the focus of a fierce debate: does donning a brimmed, bonce cover elevate your look to the ‘peak’ of all that is stylish and contemporary? Or is it a one-way ticket to the sartorial naughty step? It’s an argument that has split the fashion world down the middle for decades, but as time progresses, a growing number of men are beginning to realise that, like beanies, the real question isn’t if we should wear them, but how to wear them.

The History Of The Baseball Cap

Unless you’re completely oblivious, it probably won’t come as much of a surprise to learn that the baseball cap was first brought into existence by a baseball team. That team was the Brooklyn Excelsiors and the year was 1860. But it was another half a century before the concept fully took off. After 1900, the baseball cap became an important means by which to identify teams, as well as offering the practical benefit of keeping the sun out of players’ peepers while pitching and hitting their way around the diamond. The explosion of television sports in the 20th century brought the baseball cap into people’s homes and onto their heads. Suddenly, the piqued interest in the peaked accessory saw it become a part of the everyday man’s casual uniform. The idea of only ever wearing one on the field was now – pun fully intended – old hat.

Today it plays to the wider trend of sportswear infusing contemporary wardrobes. Combine this with the influence of hip-hop figures like Jay-Z and his much beloved New York Yankees cap, celebrities wearing them incognito, and even Gucci adding upscale versions to recent catwalk shows, and it’s plain to see why the baseball cap will always have a place as a staple menswear accessory. However, this modern essential’s wide range of variations mean it’s a famously tricky item to style. So, when it comes to picking one out, stick to these tried and tested favourites to guarantee yourself a home run.

Baseball Cap Styles

The Snapback

With its flat peak, six-panel construction and structured design, the snapback cap has become uniform for Major League heavy hitters, hip-hop heroes, hairy hipsters and countless others in between. Its name comes from the snap-closure to the back of the hat, but adjustable ‘strapback’ versions are also common. If you were looking for a classic, this is it.

The Five Panel

With its roots in performance cycling, the five-panel cap became an unlikely skateboarding icon in the 1990s, before finding its spiritual home in the the streetwear world. Favoured for its rounded, low-profile shape, the five-panel was immortalised by skate stalwarts like Supreme and Danish minimalists Norse Projects, both of which made the style its headwear calling card, sparking thousands of imitations.

The Trucker

Okay, we’ll put our hands up. We know the trucker cap isn’t exactly a must-have in the hat world. In fact, thanks to Von Dutch, Ashton Kutcher and, well, truckers, it’s quite the opposite. But there’s still hope. Pick out the right one, team it with the right gear and it might just be possible to make this mesh-panelled pariah palatable once again.

The Dad Cap

The dad cap has been around for years, but it’s only recently that it got its name. So-called because of its resemblance to the sort of thing your old man would wear (obviously), it’s often characterised by a simple curved-peak design, unstructured body and additional details such as a faded appearance, it’s a simple lid that’s a good place to start for beginners.

The Sports Cap

The traditional baseball cap may have been brought into this world by sport, but that was over a 100 years ago. These days there’s no shortage of high-tech, lightweight fabrics and cutting-edge manufacturing processes that would make the athletes of yesteryear cry witch and probably have the CEO of Nike burned at the stake or something.

Premium

Fashion’s role in forcing the baseball cap to grow up can’t be emphasised enough. The introduction of quality materials, textured fabrics and stripped-back, minimalist designs helped to turn headgear from something out of Fred Durst’s walk-in wardrobe to a stylish accessory that could, at a push, even be worn with tailoring.

Ways To Wear A Baseball Cap

Luxe Minimalism

We men owe a lot to those stylish Scandinavians, so what better way to doff a cap to them than by going understated, clean and minimal in the headwear department? And everywhere else, for that matter. Tactile fabrics like suede, wool and corduroy are all great options for affording your headgear a touch of luxury; particularly when paired with classic wardrobe staples such as a lightweight jacket and slim-fit chinos.

Summer Ready

When it comes to true summer essentials, a baseball cap is up there with warm tins of beer, a sand-filled picnic and sunscreen. But more than just being a way of avoiding forcibly squinting at the sun, the right style can also add some personality to a bog standard shorts and T-shirt look. On warmer days down at the beach or in the beer garden, use your cap to tie your outfit together by picking one in the same colour as another part of your outfit – be it your shirt or your sandals. Just make sure your chosen topper also goes with the other layers in your bag for when day drinking inevitably becomes a night session.

Tonal Tailoring

If you’d told someone in the nineties that in two decades’ time people would be wearing baseball caps with suits , they’d probably have choked on their 3D Doritos and dropped their Walkman. Yet, here we are. This look is as contemporary as they come, and the perfect way to wear a cap without looking like an angsty teenager. Simply pair a plain, premium-looking cap with an unstructured blazer worn over a T-shirt and finish with and a pair of crisp sneakers. Even someone from the nineties couldn’t say that doesn’t look great.

From The Streets

The love affair between high fashion and streetwear is still very much in its honeymoon period. However, the look can be more than a little OTT for most people’s tastes. So before you rock up to the pub in a floor-length Vetements anorak and a pair of Ozweegos, consider giving a nod to the scene in a more subtle manner. Opt for a 5-panel or dad cap style, along with a hoodie or logo T-shirt and some cropped trousers or jeans. That way you can embrace the streetwear aesthetic in public, without looking like a try-hard.

Transitional Topper

The two annual periods of limbo between the scorching heat of one season and the frigid cold of the next can be notoriously difficult to dress for. But ditching the bobble hat or bare head for a baseball cap is a great place to start. Navigate such style seas with a wool/twill cap (depending on season), then throw on your favourite transitional jacket and layer underneath accordingly.

Tips For Wearing A Baseball Cap

Take the sticker off the brim, for the love of God. You’re not 50 Cent.Make sure it fits snug on your head. There’s nothing like frantically chasing a windswept cap down the street to ruin your carefree look.On the same note, make sure it’s not cutting off your circulation. A big red line across your forehead isn’t likely to elevate your look either.Wear it backwards seldomly and carefully. Never wear it sideways.Opt for simplicity over showiness wherever possible. A plain cap is classier and will go with more of your wardrobe.If you’re going to wear a cap for the day, make sure hat hair isn’t going to be an issue later on.