What Hat Would James Bond Wear with a Suit Today?

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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
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?

27 COMMENTS

  1. It’s funny, Connery wearing a hat in the early 1960s looks very natural. Raises no eyebrows. But 10 years later, he would stand out. It is funny how fashion changes.

    There are times when not wearing a hat looks unnatural. I recently saw Enola Holmes on Netflix because I am a Holmes buff. They had Henry Cavill playing Sherlock. Aside from his arms being so bulked up that he could’t place his arms flat against his side, he wore no hat, which looked so very out of place in 1881.

    Also, you forgot the Hilary Bray hat worn as part of Bond’s disguise. It wasn’t “Bond” but it looked good in context.

      • Very nice article, Matt. I am in my forties, I live in Italy, I often wear a suit and I like to wear a felt trilby in winter very much. I have three, and match them with suit and overcoat. I don’t care how much it looks out of fashion. The current era, in fashion, has got an advantage, if any: anyone feels free to do what he likes. There are not strong fashion trends and “must-wear” anymore. So I enjoy my trilbies, look very stilish around the streets of Rome, and subtly recall the Connery years….

  2. I went through a phase in my late teens and early twenties of wearing traditional wide brimmed fedoras with my suits, and I can attest that it comes across as very costume-y, much to my chagrin. I learned after a while that I had received a level of infamy in my small Australian home city (pop. 100,000) as that fella who might be Jewish, or dressing up as Abraham Lincoln, or that I was Amish, or a preacher, or some other inane speculation.
    I eventually stopped wearing them very often, more to do with changing my hairstyle than anything else. I really do think they’re practical and I lament that hats have fallen so out of favour. I’ve taken to wearing flat caps with my cardigans which tends to be received much more favourably, or at the very least unnoticed. I still keep my panama hat for those scorching summer days that looks fairly acceptable with a cream jacket or linen suit, no queer sideways glances will stop me protecting my body from sunburn.

  3. Felt hats don’t really serve any practical purpose as they do very little to protect against cold. Fur hats protect the wearer perfectly, but wearing a fur hat might pose a challenge, as it is certainly an unusual look nowadays even in the countries where wearing fur hats in cold weather was common practice half a century ago (e.g. Russia). That being said, any hat (except a straw hat) is easier to style when wearing an overcoat.

  4. Hello Matt,
    There is a very nice behind-the -scenes pricture of Sean Connry and Terence Young on the set of FRWL with the Scotsman wearing a flat cap with a suit and peak-lapel overcoat which show the style works on Sean. But perhaps not on Bond…There are also quite a few pictures of Terence Young wearing them and we know the influence he had on James Bond’s style.
    Best regards

  5. I think a straw hat in a Fedora style, in a sunny location, would be a good way to introduce the hat again. With a short sleeve linen shirt and linen trousers.

  6. I don’t see any hat looking right on Bond with a suit today, and I say that as an avid fedora wearer myself. As you identified, he would either look too old fashioned in a trilby or fedora, or too casual in any kind of woollen hat or flat cap. The only hat I could see working at a push would be some sort of fur hat like an ushanka in extremely cold locations where it would not look out of place. Personally I would like to see him in a trilby or fedora because those hats look best with a suit in my opinion, and if they are worn well with proportions that suit the wearer and the rest of the outfit they don’t look costumey.

    As to the reason for the decline in hat wearing, I think the increase in car ownership and the general trend towards more casual clothing post-WW2 were the main factors. Hats lose their practical function if you are travelling by car and have only a short walk between your car and office/home. I don’t think JFK had much impact, as hat wearing was already in decline by the time of his inauguration.

    • Cities in the mid-20th century also had a lot of soot and smoke pollution compared to later in the century. Might have been a factor in the utility of a hat for men and hair-scarf for women whenever outdoors. I don’t wear (proper) hats in cool weather, but find that a straw or other lightweight and light-coloured hat is great against hot sun.

    • It’s not just car ownership, but safety mandates in cars as well. At least in the US, headrests have been mandatory since the late 1960s, which make it very difficult to wear a hat with a full brim.

  7. Thinking of it, wasn’t Daniel Craig, in character, wearing some sort of hat with an overcoat in the wintery Heineken Skyfall commercial? Maybe I was distracted by Berenice Marlohe…

  8. I used to wear a fedora. Nothing was wrong with it, except, well, hat hair.

    These days, I don’t even gel my hair anymore, but I still wouldn’t wear a hat, again, because, hat hair.

    But if I’m brave enough, I might just wear a trilby in the near future. As for now, my Ray-Ban will do well for what I want and need.

  9. The new Bond could contribute to revitalize the trilby/fedora, just like Craig did with the shawl cardigan.

  10. Matt,

    What do you think about hats like the trilby being old fashioned in the way 3 piece suits are? Or do you think it’s different? I remember in the 80s my father wore a 3 piece suit frequently when I was young, but by the mid 90s his office was what we refer today as business casual. When I first started as an attorney in 2008, 3 piece suits were almost never seen. I have seen more in the last few years prior to Covid and again as we begin moving on from it, but generally on older men where, like a trilby, they look better, or on dandier types of younger men. I have always liked the look of a 3 piece, but not wanting to stand out I have eschewed them for the most part (I have one suit that is a 3 piece but I have only worn the vest a handful of times, mainly because the trousers are too low cut and it doesn’t look good with the shirt showing occasionally).

    • The three-piece suit is not a whole lot different from the two-piece suit. Both are suits. The trilby and other felt hats can’t be compared to anything else. That’s why they look more old fashioned.

  11. Another great entry Matt.
    As for your original question – I think the producers missed an opportunity to get Bond hatted at the end of QOS in Kazan. In a heavy overcoat outdoors with snow falling a brimmed felt hat (trilby or fedora) or something more exotic / local like a ushanka or karakul could have been deployed.

    Conversely, a pale skinned Blondie like Craig could have got away with a panama for some of the scenes in Jamaica in NTTD.

    As a pale skinned Blondie myself I often say that if anyone is nervous about dipping their toe into the hat pool, get a panama and wear it on holiday. There will be nobody else you know there to poke fun and dent your confidence, and any other anxiety can be dampened by the sheer practicality of wearing a light summery hat in a hot location to shield the eyes and protect the forehead from sun damage.

    Panamas are very versatile – allegedly made popular by the labourers working on the Panama Canal so they’re at home with workwear. A classic fedora style can look equally good with a polo and shorts at the beach or with formal businesswear. I have several in several colours aside from the standard beige, and often wear them in the summer months for work, along with linen blazer, shirt and tie etc. They are also the perfect complement to an outdoor summer / beach wedding no matter the level of formality.

    • PS forgot to add – another reason for the decline in popularity of hats was the decline in popularity of hat check booths at bars, restaurants and clubs. Many restaurants used to have a large hook on the side of the screens separating booths but they are very rare these days, as are coat rack / hat stands in public buildings. Also chairs used to be made with the horizontal slats beneath the seat which was a perfect place to keep a doffed hat safe from marinara sauce but they are all too rare these days too.

  12. I can see Bond wearing a hat again if the context is to use it to conceal a gun (cf. Harry Palmer) or other weapons/gadgets such as razor blades (cf. Peaky Blinders), etc.

    • I can see Bond wearing a hat to secure some kind of documentation device captured from the opponents as well.

  13. I’m a personal fan of hat wear. I actually like to collect vintage hats and wear them on different occasions. I would not mind to see Bond wearing a hat again. However Bond did wear a top hat during the Day of the Dead celebration. I live in a rural area and many people love my hat choices.

  14. I have a Cuban, basically a straw trilby, that I wear during the summer, but it doesn’t look like costume since it serves a purpose. It’s in natural straw, so it really doesn’t work with business suits, but I wear it with casual clothes and more sporty suits, like my cream silk one. If I bothered to get one in gray it could work with business suits in the summer as well.

  15. Hat-wearing is a major perk of being older. I remember getting a fairly nice fedora (fairly western-styled but not a cowboy hat) when I was in my 20’s. Rarely wore it except for when it was pouring the rain. I see a lot of smooth-faced young guys try the Crocodile Dundee style or even gangster-ish fedora, and it just looks cartoonish.

    Now that I’ve got a fair amount of gray in my beard, that fedora is getting worn out and I constantly get compliments on it. I’m about to need to replace my Panama, too. While I never go outside without one or the other (or a flat cap), the fedora always has to get taken off in the car due to the headrest. Headrests are likely a large part of why wearing brimmed hats has declined (that and the lower roofline to accommodate a sunroof).

    Sunglasses are fine and dandy, but they don’t protect your head and neck from the sun’s rays or the weather.

    We’ll just have to see what the next 007 wears (or if it’s even a guy… don’t even get me started) but if that Bond is old enough, I would think the trilby would still be the go-to.

  16. As a bald guy of 58, I love my hats and caps, just adjust to whichever outfit one is wearing. I bought my first trilby in 1982.

  17. Speaking as someone who has worn wide brimmed hats consistently (narrowest brim I’ve got currently is right at 2.5 inches/64 mm) since the last couple years of high school through my post-collegiate years and is now currently in my early 30s: the answer to the question is he wouldn’t. As utilitarian an accessory as they are, the kind of hats you’d potentially see Bond with in a suit – as Bond and not as part of disguise – are largely an affectation and have been for the past six decades. Hate to admit it, but it’s true.

    Now with that said, I absolutely can see him in a casual outfit with some sort of more utilitarian hat. Like a knit for a winter mission, or a panama in an introductory scene to a tropical locale. But a hat with a suit for Bond does not feel like something that will happen again until either Eon decides to start readapting the books as 1950s-set period pieces or the sorts of hats that could work with suits for Bond go through a massive international revival, whichever happens first.

    • Good post and let’s not forget that like it or not, wearing a brimmed hat these days is likely to make you stand out, which is not exactly desirable when you’re a SECRET agent!

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