We see James Bond in swimming trunks, pyjamas and dressing gowns, but we never see James Bond in his underwear in the films. There’s a slight peak of it in Casino Royale, but we can’t tell what kind it is. Bond most likely has varied his underwear styles throughout the decades. Ian Fleming specified “nylon underclothes” in the novel Diamonds Are Forever, which have great drying properties. In The Man with the Golden Gun novel, Fleming wrote about a different, more luxurious type of underwear:
Bond then took off his clothes, put his gun and holster under a pillow, rang for the valet, and had his suit taken away to be pressed. By the time he had taken a hot shower followed by an ice-cold one and pulled on a fresh pair of sea island cotton underpants, the bourbon had arrived.”
The “sea island cotton underpants” are undoubtedly referring to the woven boxer short style, since old-fashioned men in Britain at the time wore little else. The cotton material would be similar or identical to Bond’s sea island cotton shirts that Fleming specified. Some shirtmakers make boxer shorts to match their customers’ shirts. Sean Connery and Roger Moore most likely also wear woven boxer shorts as Bond, considering that was traditionally what men wore in Britain. Roger Moore can be seen in cotton boxer shorts in the 1969 film Crossplot, which took its wardrobe from Moore’s television show The Saint. Connery’s and Moore’s trousers have enough fullness in the thighs to accommodate boxer shorts.
In the unofficial James Bond film Never Say Never Again, Sean Connery wears cream boxer shorts with a white vest (also known as an A-shirt). Bond had just discarded his dinner suit to escape on a bicycle, so he must have been wearing these clothes under his dinner suit. The British ordinarily aren’t fond of undershirts, and Bond almost never wears them. To blend in as an American in Fleming’s novel Live and Let Die, Bond wears “nylon vests and pants (called T-shirts and shorts)”. However, the “nylon underclothes” that Fleming writes about in Diamonds Are Forever may also include vests.
Underwear is a very personal garment and there’s no way we can guess the different styles of underwear that Bond has worn throughout the series apart from following what the trends were at any given time. Trends in underwear sometimes followed trends in trousers. Boxer shorts were very popular in the 1980s and 1990s when full-cut trousers were popular. However, in a 1985 episodes of Remington Steele titled “Forged Steele”, Pierce Brosnan wears white knitted cotton briefs.
The James Bond Dossier announced last month that Sunpel, who made some of Daniel Craig’s polos and t-shirts for Casino Royale, has provided their stretch cotton brief and their stretch cotton low waist trunk (a short boxer brief) for Daniel Craig to wear in Spectre. This underwear is made of a 92% cotton and 8% elastane blend so it has more stretch than a pure cotton knit. Neither the brief nor the trunk has a front opening. Briefs and trunks are necessary for Daniel Craig since loose boxer shorts would bunch up under his tight trouser legs and prevent the trousers from hanging smoothly over the thighs.
What kind of underwear do you think Bond would wear?