Hats On

Hats are a major source of dressing up fanfare, which means now is a good time to invest in a well crafted chapeau.
Hats On
Convention once meant that a hat was a gentlemanly necessity, where no second thought was given. Staid traditions of this nature are largely behind us, which has seen classical hats now wholeheartedly embraced by style conscious men. They're seeking to express their individuality and flair from a perspective of creativity rather than adhering to convention.
Sammy Davis Jr. as Sportin' Life in Porgy and Bess. (Photo by Gjon Mili/The LIFE Picture Collection via Getty Images)
Frank Sinatra in recording studio (Photo by GAB Archive/Redferns)
George Raft (Photo by William Grimes/Michael Ochs Archives/Getty Images)
Lauren Bacall and Humphrey Bogart in Paris
Paul Simonon of The Clash in front of a car at JFK Stadium in Philadelphia, PA. September 25, 1982.  (Photo by Bob Gruen)
Gardner McKay,  Hollywood, 1959. (Photo by Allan Grant/The LIFE Picture Collection/Getty Images)
Fedora With a soft brim and indented crown, the fedora is synonymous with Old Hollywood. No one quite epitomised the glamour of the fedora quite so pertinently as Humphrey Bogart in the Oscar-winning film Casablanca, 1942. Despite the fedora’s style credentials, it does keep your head warm, and whatever the season or state the world is in – a well-made fedora is always an excellent hat to have resting on your hatstand.


Artie Shaw with Lana Turner, arriving in New York by train in 1940 (Photo via Getty)
Beanie The knitted beanie is the most casual headwear option. Originally favored by hippies, Beat poets and people of naval vocations, the design has become shorter and more refined, where it now regularly features on the runways for luxury fashion houses. Jacques Cousteau’s iconic red beanie is one of the first to spring to mind from naval backgrounds. The use of red was initially a safety measure to stand out at sea, but became his signature. It is thought you lose most heat out of your head, so why not choose the warmest hat (the beanie) as your hat for long walks in the park.
The Rake, Skiing, Prince Charles, Princess Diana
Prince Charles and Princess Diana
The Rake, 5 Ways to Wear a Hat, Jacques Cousteau
Jacques Cousteau, 1973
Flat Cap Thanks in part to Peaky Blinders and the ever-increasing desire for more informal dress, baker boys and flat caps have been re-adopted in a big way. The structure and design of the peaked cap allows for a wider variety of fabrics to be used, The imbalance of pairing a peaked hat with a tailored jacket, shirt and tie, just like Jean-Paul Belmondo did in Breathless, 1960 makes for a more rapscallion appearance on streets of Paris.


Rocky Sylvester Stallone
Baseball Cap The use of baseball caps for something other than sporting excursions can divide opinion. Very much down on the casual spectrum, its credentials have never been so appropriate.
American astronaut Neil Armstrong lights a cigar, Houston, Texas, March 1969. (Photo by Ralph Morse/The LIFE Picture Collection via Getty Images/Getty Images)
Smoking Hat The festive season is usually the time when you see a smoking hat, whether it be on film or one your father has fetched out for some mild laughs. Humour aside and to stop your hair from smelling of cigar aromas, New & Lingwood’s navy renaissance-print silk smoking hat, with tassel is a foppish winter accessory; put it into into practice with a fat Cuban cigar from Hunter & Frankau, whilst seated in comfort next to the fire.
Navy Renaissance-print silk smoking hat from New & Lingwood