Like a cross between a polo shirt and a plain tee, with a partial button-up placket but no turn-down collar, the henley started out as 19th-century underwear. Given the absence of collar, which hitherto came as standard on most undies, it was heralded as being comfortable and practical, coming as it did in cotton for summer and wool for winter.
Menswear legend has it that these characteristics led to the style being adopted as the default uniform for rowers in the town of Henley-on-Thames (hence the name) in Oxfordshire, which since 1839 has been the site of the Royal Regatta. This gave rise to a tradition whereby the vanquished crew had to give their shirts to the victors, which doubtless provided extra motivation for chilly days on the river. (A distant cousin of the henley also became popular across the pond for playing baseball, although it typically buttons all the way down.)
Supposedly the henley remained confined to the realms of sportswear and underwear until the 90s, and specifically an incident recounted by the journalist Michael Gross in his biography of Ralph Lauren, Genuine Authentic. A New York merchant showed a vintage three-button long-sleeve henley by Johnstown Knitting Mills to one of Ralph’s buyers, who remarked, “This is a new shirt.” Clearly it was an old shirt, but he meant that the style was ripe for wearing not just as a base layer. This was ably demonstrated by the actor Ryan Gosling in the movie Drive; his henleys were also vintage, dating back to the 40s, and sourced from a store called Mister Freedom in Los Angeles.
D F Meineke Of South Africa At The Henley Royal Regatta, 30 Jun 1955. © Associated Newspapers / REX /Shutterstock.
David Beckham after the birth of his son Romeo outside the Portland Hospital, London, UK (2002). © REX / Shutterstock.
Like the polo shirt, the henley carries athletic connotations; left unbuttoned, it is extremely effective at showing off a powerfully built chest. (See Ryan Gosling.) But unlike the polo, the henley is not associated with a particular fabric, available in everything from lightweight versions to heavier, quilted ones that hark back to its rowing origins. The former lend themselves well to being layered under an overshirt, especially one with a suitably rugged military, lumberjack or western (denim) vibe, but the latter can also be worn over a T-shirt, with the crew-neck visible poking through the placket.
It should be noted though that part of the reason why Ryan Gosling looked so good in his henley was that he filled it out admirably. If your physique is not quite regatta-ready, then it might be an idea to familiarise yourself with the rowing machine at your gym.
Ryan Gosling, Carey Mulligan and Kaden Leo in the movie Drive (2011). © Snap Stills / REX / Shutterstock.
White Henley Style Long-Sleeve Top
Navy Henley Style Long-Sleeve Top
Navy Long Sleeve Slub Effect T-Shirt