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.”

Baseball caps firmly belong in the casual realm, says McCalla, working best in a dressed-down approach. “Think jeans, trainers and a shirt for a timeless look. Or you can also do smart-casual for the risk-takers – chinos and an unbuttoned Oxford shirt nod to the diamond without overdoing, which is why you should avoid actual baseball threads or collars lest you look like an extra for the Yankees.”

So, with your thinking cap firmly corrected, these are the only baseball caps to consider this season.

(Related: How to wear a hat without looking like a fool)

zara aw15 saturdays surf nyc ss15 h&m ss15 banana republic aw15

Carhartt WIP Backley Cap

If American workwear has gone fully viral, consider Carhartt patient zero. The New England outfit has long crafted durable, wardrobe staples, with the WIP line – short for Work In Progress – adding caps and the like for a more contemporary edge.

Available at The Idle Man, priced £29.

Ralph Lauren Polo Cotton Twill Baseball Cap

Ralph Lauren’s Polo line has long been repurposed for cool streetwear looks, and the baseball cap is no exception. Style with wide leg trousers, white tees and a crisp Oxford shirt.

Available at Mr Porter, priced £30.

Stone Island Classic Embroidered Baseball Cap

No longer associated with chair-throwing hooligans, Stone Island’s range of baseball caps are now as welcome at Milan as they are at Millwall. What’s more, limiting the brand to simple accessories is way more subtle than going full tracksuit.

Available at Matches Fashion, priced £75.

New Era New York Yankee Baseball Cap

The New York Yankees cap is one of the most popular ways to top off an outfit, with the likes of Jay-Z, Orlando Bloom and even Harry Potter (well, Daniel Radcliffe) nodding to the East Coast major league.

Available at Selfridges, priced £10.

Nike Swoosh Baseball Cap

The New York Yankees take the throne for the most iconic baseball cap. Nike, however, is very much the crown prince. If you prefer getting your head into something more minimalist, America’s biggest sports brand deserves your coronation.

Available at ASOS, priced £13.

Stüssy Smooth Stock Strapback Cap

Stüssy may have Californian surfwear origins, but today, the American label is a firm streetwear go-to. Case in point, the multitude of caps that are more A$AP Rocky than Rip Curl.

Available at Size?, priced £37.

River Island Yellow Copenhagen Baseball Cap

A choice cap needn’t flex big branding to complement your look. River Island, keen to espouse the best of British, can provide the full stop to a streetwear get-up that won’t finish your bank balance.

Available at River Island, priced £12.

Saturdays NYC Stanley Miller Printed Shell Baseball Cap

Less a bona fide surf brand and more an homage, Saturdays NYC melds West Coast cool with city temperaments in its range of caps. Which translates to grand slogans relating to the Big Apple housed within relaxed Californian shapes.

Available at Mr Porter, priced £45.

Wood Wood Beige Pink Baseball Cap

Add some Scandi minimalism up-top with Wood Wood. The Danish answer to Supreme boasts a line of baseball caps that pares down on the streetwear statement (and the six hour queues).

Available at Zalando, priced £29.99.

Les Basics Le Peak Baseball Cap

Why the term ‘basic’ is levelled as an insult, we’ll never know. Les Basics – a Portuguese label known for unrivalled simplicity – instils a baseball cap range with the same pared back approach.

Available at Flannels, priced £45.