Baseball caps have endured more highs and lows than a Prince song. Just think, the preferred headgear for teenage terrors of the nineties is also the celebrity disguise of choice, not to mention a campaign-trail fixture for a certain Mr President with a certain dubious slogan.

Yet credit where credit’s due. Despite the onslaught of bad press, baseball caps have retained an essential spot in men’s wardrobes generation after generation. Just without the Burberry checks or promises of greatness – two things that occurred way after the baseball cap’s birth in 1860.

First worn by amateur baseball team the Brooklyn Excelsiors, the founding father was originally designed to shield players’ eyes from the sun. That entailed a long-peaked cap – a big departure from the Peaky Blinders styles of the era – with a button to the crown. Later designs in the 1940s encompassed a latex material to the interior, a way to add structure and stiffen the material from within.

Since that initial home run, the baseball cap has been employed by various designers, subcultures and even the armed forces, with US submarine forces donning a red iteration for some officers. For civilians however, the piece still requires deployment with military precision.

“The key to a baseball cap is keeping it clean and simple, with little to no branding and nothing too loud,” says Alexander McCalla, stylist at Thread. “Neutral tones always work best; navies, greys, black or khaki are particularly good, as they work with most complexions and they’re easy to integrate into an outfit.”

The rules don’t end with colour, either. “Factor in shape and material, too – the go-to is standard cotton. Consider your head shape, too. A flat peak, New Era cap might not suit your skull, while curves or five-panels can be a little more forgiving.”