White T-Shirt

It’s hard to imagine what life would be like if arguably the most iconic menswear item in the world remained nothing more than an undergarment.

“It’s not so much a trending piece as a perennial relied upon by many,” says Henry Wilfrid, a men’s stylist who has worked with brands including Tom Ford, Dunhill and Reiss.

The most classic version of the T-shirt, a short-sleeved white cotton crew neck, first sprung to life as standard issue schmutter for the US Navy and later the army in the 1910s. When the war ended, tens of thousands of soldiers took the fashion home with them. Brando, Dean, Beckham. The rest, as they say, is history.

Pilot’s Watch

Ever since man first took to the skies, watchmakers have been working hard to create a ticker to help him land at his destination on time.

The pilot’s watch is the fruit of their labour. “It’s a great example of function over form,” says Terry Markham, head of buying at WatchShop.com. “The beauty of the pilot design is that it comes in a simple colour palette, is easy to read, is not overtly branded, and wears well dressed up or down.”

One of the most popular choices on the market, the best pilot’s watches are chronographs with features such as unidirectional bezels, lumed hands and are flanked by either a leather or nato strap.

The Bomber Jacket

Like most military clothing, the bomber jacket was originally developed as utility wear, designed to keep pilots warm in cockpits so rickety and thin that freezing was as much a risk as being shot out of the sky.

Early styles were cut from heavy-duty leather and lined with insulating sheepskin (more closely resembling what is now known as an ‘aviator jacket’), but today it’s more common to see the nylon MA-1 model flying up and down runways.

“The bomber jacket has been a key piece for a few seasons now,” says Wilfrid. “For a more formal interpretation, look out for leather trims or even styles made with a velvet fabric.”