James Dean.
James Dean.
Image: Wikimedia Commons

As with all things built to last, a solid foundation is imperative. With the basics right you can express yourself, show your taste and embrace trends.

We continue with our series on foundational items of clothing and accessories that make up the core of a well-presented gentleman’s wardrobe.

 The T-shirt embodies the spirit of rebellion and insouciance like no other garment except, perhaps, denim jeans. As we make way for Spring and pack away heavy knitwear and tweed jackets we unpack the history of the ubiquitous T-shirt and its undeniable impact on popular culture.  

Introduced by the US Navy at the turn of the 20th century, the crew neck T-shirt was adapted from an earlier long sleeve onesie-type undergarment called the union suit. The short sleeve T-shirt was issued to servicemen to wear under standard issue shirts and jackets which provided a moisture-wicking barrier between the body and the uniform, keeping the wearer looking sharp while on duty. Cut close to the body and relatively high on the neck the T-shirt also covered any chest hair which was considered unkempt. The round, collarless neckline got its name from the “crews” that wore them and the “T” from the shape it formed; arms outstretched.

The T-shirt quickly gained popularity within the military fraternity but it wasn’t until 1950 that it gained broader appeal after Marlon Brando pushed the boundaries of appropriate dress code and donned the undergarment as outerwear in the movie A Street Car Named Desire. A couple of years later, inspired by Brando, it was James Dean in Rebel Without a Cause that cemented the crew neck T-shirt’s status as a men's wear staple.

Fuelled by their good looks and rebellious streak in equal measure, Brando and Dean pushed back at the bespoke tailoring that defined Hollywood masculinity espoused by the likes of Clark Gable and Cary Grant. The T-shirt represented the blue-collar everyman.

As the 1960s ushered in a social revolution, T-shirts captured the zeitgeist with colourful expressions of tie-dye prints and hand-painted flowers and peace signs. The 1970s just didn’t carry the torch, they practically threw fuel on the anti-establishment fires with the rise of subcultures such as the punk scene. Mainstream fashion designer Vivienne Westwood made strong statements with bold slogans and deconstructed silhouettes. The current iteration of the T-shirt was largely influenced by hip-hop and streetwear of the 1980s, characterised by oversized silhouettes and dropped shoulders.

Whether you’re a skater, a death-metal rocker or a flat-white sipping, tote carrying, box logo wearing millennial, there is a T-shirt for you. While I wouldn’t dare tell you how to wear yours, I thought I’d tell you how I wear mine. I have no issue that the accepted definition of business casual these days can be anything from a hoody thrown over a T-shirt and jeans to a two-tone khaki shirt with short shorts from the farm supply store.

For me, though, fit is crucial. Slim, never tight in 100% Supima cotton if I can find it. White, black, navy and grey melange are my go-to colour options with pops of olive or military green to keep things interesting. Nautical stripes are as far as I’ll go with prints. I generally steer away from overt branding or logos. As a rule, if you can read it from three metres away, it’s not for me.

I find the trick to wearing T-shirts as an adult is layering. With exception of going for a run, I will always wear a T-shirt layered under some piece of outerwear. A denim trucker jacket with a crisp white T-shirt and khaki chinos and Chuck Taylors for running errands on a Saturday morning. The denim jacket can be swapped out with a French chore coat or a Harrington jacket, depending on the weather. A navy blazer in linen or cotton over a dark T-shirt and indigo denim jeans and suede boots or horse-bit loafers for date night.

In 1997 Apple introduced the Think Different ad campaign, arguably one of the greatest advertisements of all time. However you decide to wear your T-shirt, I’ll leave you with the opening line from that ad:

Here’s to the crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes ... the ones who see things differently

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