What Hat Would James Bond Wear with a Suit Today?

Wearing hats stylishly today is a challenge, and it’s particularly difficult to wear a hat with ease while wearing a suit. Dressier hats have fallen out of fashion and on many men come off looking like costume. But as they go the way of the dinosaur, hats still serve a practical and necessary purpose, whether its to keep one’s head warm in cold weather or to keep the sun off the head in the heat. Is there a solution for what men—and what James Bond—can wear to cover the head in a modern way while wearing a suit?

Bond’s Hat History

Bob Simmons Gun Barrel walking

Bob Simmons Gun Barrel walking

The first image of James Bond in the film series, played by Bob Simmons wearing a trilby

The trilby was an integral part of Bond’s look in the 1960s, featuring in all six Bond films of the decade, even if some appearances only show Bond carrying the hat. The trilby is an English hat of felt or tweed with a narrow brim turned up at the back and a short, tapered crown. It’s in every gun barrel sequence from the era as well. Bond wears felt trilby hats with many of his suits, and he wears a more formal homburg with his dinner jacket and chesterfield coat in Dr. No. Hats were still a complete part of a business outfit in the early 1960s, and men often wore them to stay warm, cool, dry or clean outdoors.

Bond’s first trilby in 1962’s Dr. No was from Lock & Co., and Connery’s others may have also come from them. Bond still has the trilby in the gun barrel sequence in 1971’s Diamonds Are Forever—the sequence was originally filmed for Thunderball in 1965—but it’s nowhere to be seen in the film. New fashions were in, and the hat had fallen out of favour. At the time, the narrow-brimmed hat would have looked old-fashioned and square, and the narrow brim would have clashed with the wide lapels on the suits.

Bond tosses his trilby to Moneypenny in 1969’s On Her Majesty’s Secret Service, and he doesn’t get it back until 1981’s For Your Eyes Only

The trilby returned in Roger Moore’s three Bond films of the 1980s, For Your Eyes Only, Octopussy and A View to a Kill, but only for Bond to throw on the office coat tree. It was a symbol of Bond leaving the silly 1970s behind and returning to his origins. It also signified a return to more classic and conservative style. Though these films brought back a traditional edge to Bond, it would have looked too old-fashioned to see Bond wearing the trilby again, and it wouldn’t have provided enough room for Roger Moore’s voluminous hair. Moore didn’t wear a hat as Simon Templar in the 1960s when Bond did, possibly because his even larger pompadour wouldn’t have fit under the fashionably smaller crowns of the decade.

Moore does wear a bowler hat in his 1970 film The Man Who Haunted Himself to portray his character as a conservative and stodgy London businessman, and he has a new, less voluminous hairstyle to go with it.

The only hats Bond wears going forward are part of uniforms. He wears naval caps in The Spy Who Loved Me and Tomorrow Never Dies to match his naval uniforms. The hat here has a special context so Bond looks appropriately dressed.

He also wears grey top hats with morning dress on two occasions, to follow the uniforms for Royal Ascot in A View to a Kill and Felix Leiter’s wedding in Licence to Kill. Again, the context of the hats makes them look appropriate on Bond and not old fashioned.

Why Did People Stop Wearing Hats?

Americans like to cite President John F. Kennedy as a reason why people stopped wearing hats because he did not wear one at his 1961 inauguration, but he did indeed wear a top hat on the day. However, like many people in the 1960s, Kennedy was wearing hats far less frequently than previous presidents did.

The supposed Kennedy influence to wear hats less wouldn’t apply to people outside of the United State,s who wouldn’t have cared what Kennedy wore or didn’t wear. James Bond still wore hats for years after Kennedy was inaugurated. Significant changes in fashion usually come from practical origins, as much as we like romantic stories about the fashion influences of presidents, kings and princes. Celebrities influence fashion in the short-term, but long-term changes need more substantial reasons.

While hats took longer to fall out of fashion in the United Kingdom than they did in the United States, they fell out of fashion in the 1960s in both countries. The increasing use of cars is thought to be the primary reason why hats went out of favour. Cars in the 1960s typically had lower roof lines than cars of a decade earlier, providing less room for hats to be worn inside them. Men were also growing tired of the formalities of hat wearing.

The trilby would have ruined Roger Moore’s hair

Hairstyles were also changing and didn’t play well with hats. Men’s hats of the first half of the 20th century were designed for neat and trim hairstyles, not the longer and shaggier hair styles that were becoming fashionable.

By the end of the 1960s in On Her Majesty’s Secret Service, James Bond was still wearing hats. The brims were narrow to follow the fashions of the decade, but the hat was quickly falling out of favour and painted Bond as a conservative Englishman and a traditionalist.

What Hat Would Bond Wear with a Suit Today?

In the wintertime, an overcoat alone isn’t always enough to keep a man warm with a suit, particularly if he needs to be outdoors for any length of time. Hats and hoods serve a practical and necessary purpose, no matter how we’re dressed, but today’s usual choices for headgear do not look right with a suit.

Bond has not donned a hat with a suit since the 1960s. While Connery looked cool in his trilby in the 1960s, it looks old-fashioned today, as does any kind of felt hat. Many men of all ages still like and wear classic trilbies, and many still wear them well, but they’re not easy to wear. Younger men can look like they’re playing dress-up in their grandfather’s hat or in a costume because it’s unusual for them. At best they look stylish but nevertheless old fashioned or eccentric.

Older men can pull off wearing a hat more easily, and older men today wear more hats. Maybe it’s because they were used to wearing hats when they were young men at a time when hats were more commonplace. Or maybe they’ve turned to hats as they get older because they’ve lost hair, not to cover up hair loss but to shield their heads from the sun and the cold. Older men tend to look more fashionable in hats than younger men do, but that’s because we associate hats with being a more mature look.

Bond has never looked old fashioned in his suits. He looks like a traditionalist at times, but never old fashioned. Since Bond is not meant to look like an older man, his 1960s trilby might look too old fashioned on Bond in the 2020s. Still, it would look more modern than a wider-brimmed fedora.

The hats that men commonly wear today are casual hats. Caps are most common, whether its a baseball cap to keep out the sun or a knit cap (also called a watch cap, woolly hat, beanie, toque among many other names) to stay warm. Bond has worn knit caps for skiing or other casual winter activities. But no matter how luxurious the cashmere is that it is made from, it will never match the formality of a felt hat. As a purely practical item, the knit cap can work with a suit, but it won’t look formal enough. As of No Time to Die, Bond has even worn a baseball cap, which is a truly casual cap, but only for sailing.

Daniel Craig himself has long been a fan of flat caps, which can look good with a sporty suit but not so much with a dressy suit and overcoat. Flat caps have an old-world look too, but they look more fashionable today than a felt hat. Being more casual helps them fit into modern fashion more easily. In a solid dark-coloured flannel or cashmere, a flat cap could work with a suit to keep one’s head warm in a way that looks more modern than a felt hat. It won’t look as formal, but it can still look stylish and not inappropriate. But it isn’t a look James Bond has ever been associated with apart from a disguise in Octopussy.

The key to wearing a cold-weather hat with a suit today is pairing it with an overcoat. It gives a trilby, fedora or cap some context as a practical accessory over a fashion accessory. In the 1960s, Bond often wore his hats without any coat, but today the hat would only come on as a necessity when an overcoat is not enough to keep him warm.

Connery’s hat and coat go together in Thunderball

Straw hats—like panama hats—with summer suits can also look good today without looking as old-fashioned as felt hats. James Bond has never worn a straw hat with a suit, and it’s unlikely he would ever do so. He has only worn straw hats casually, like for golf in Goldfinger or to shade himself from the sun in Thunderball.

Until Bond wears a hat with a suit again, there’s no way to know for sure what kind of hat Bond would wear with a suit now. What kind of hat do you think Bond should wear with a suit today?

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