Though I don’t know if it was a trend in 1965, Bond wears a matching sports shirt and trouser set in Thunderball. And it’s in a vivid royal blue. Out of Sean Connery’s casual Bahamas outfits in Thunderball, this one dates the worst. It looks like a well-fitting set of pyjamas, but Connery pulls it off. The shirt has a camp collar, four buttons down the front, and a straight hem. The hem of the short sleeves is turned up and sewn all the way around. The back of the shirt has shoulder pleats, which are pressed all the way down the shirt. If the shirt is of the quality we have come to expect from Bond, the white buttons are likely mother of pearl.

Though we see little of the trousers, they have a tapered leg and are pressed with a crease. Bond wears black slip-on shoes—probably the same shoes we see later when Bond puts his foot in the basin—and no socks. Goldfinger and Thunderball are the only times that Bond wears a straw hat. This pork pie hat is natural straw with a blue and white checked cotton ribbon. The hat has a telescopic crown with no pinch, and a short brim that’s turned up in back. A short brim is unusual for a straw hat since it provides little shade from the sun, but it’s part of the more typical pork pie style. To make up for the short brim, Bond wears the Wayferer-style sunglasses that we see more of later in the film.

None of Roger Moore’s infamous safari suits are identical. The safari suit in Octopussy is one of the most classic, being in tan, and it doesn’t have the flared 1970′s trousers to date it. It’s now 1983, and Moore has continued to wear safari suits. And why not? It’s a classic piece of English clothing, and most appropriate for the safari that Bond finds himself being hunted in. Frank Foster said he made the shirt-jacket, and he said it’s made of worsted wool. High twist wool in a plain weave is very comfortable in warm weather, and that’s what this cloth appears to be. The lack of wrinkles in this safari suit also shows that it’s made of wool and not pure cotton or linen. Though cotton or linen would be more comfortable, wool is very durable and looks great on screen. Plus, the tan colour is great camouflage against the Monsoon Palace’s stone.

The shirt-jacket is tailored like a shirt, as a safari jacket should be. But the cut is more complex than a typical shirt. It has two front panels, two back panels and a western yoke across the shoulders with a point in the middle. The front panels have darts under the arms that extend forward to the middle of the hip pockets, and the side seams are pushed back and have deep vents. There are four buttons down the front, on a wide placket. The collar is a formal-shirt-type point collar, but larger and without a button. The front has four patch pockets with box pleats and pointed button-flaps. The sleeves end in shirt-style cuffs, fastening with a single button. Completing the safari shirt look are the essential shoulder straps. The trousers have a flat front and straight legs. Here in light brown are Moore’s usual—but inappropriate—slip-on shoes.

A close-up of the open-weave cloth and Seiko G757 digital watch

Marc Ange Draco (Gabriele Ferzetti), the father of the bride, wears the most traditional version of black lounge at James and Tracy Bond’s wedding. Draco’s button one lounge coat has notched lapels, flapped pockets, three-button cuffs and no vents. The shoulders are straight with roped sleeveheads. The waistcoat matches the jacket in black and has six buttons with five to button. The trousers are in the traditional cashmere stripe pattern, cut with a flat front and most likely worn with braces.

M wears a less formal ensemble with light grey trousers and a cream shirt, and without a waistcoat

Draco’s white shirt has a small spread collar with mitred barrel cuffs. Whilst a striped tie isn’t the traditional choice for a wedding, the colour scheme is right with black, silver, white and pink and is perfect for the occasion. The stripes go in the British direction, from lower on the right-hand side to higher on the left-hand side. The shoes are black, and most likely they are cap-toe oxfords. With the rest of the wedding party, Draco wears a white carnation in his lapel.

Felix Leiter, James Bond’s American counterpart, has never been as cool as when he was first portrayed by Jack Lord in Dr. No. Lord’s successor Cec Linder plays Leiter as a stodgier character, dressed in Ivy League style, whilst Lord dresses younger and more fashionably. Since it’s only 1962, the suit has a lot in common with 1950s styles. The suit is made in beige tropical wool. The button three jacket has padded shoulders with roped sleeveheads, and a relaxed cut through the body with front darts. The back has short double vents—a popular 1960s style—that are no deeper than 6 inches and are more for style than for function. The hip pockets are welted like the typical breast pocket, another style that was more commonly seen in the ’60s. The lapels are a little on the narrow side, with tiny notches. The cuffs have three buttons, spaced out, and the suit’s buttons are light brown horn. The suit trousers have a flat front, cross pockets, side adjusters and turn-ups.

Leiter’s white shirt has a spread collar, double cuffs and a front placket. The tie is solid dark brown. His shoes are brown moccasins. His most well-known accessory is his pair of cat-eye sunglasses, which have since become primarily worn by women. Nevertheless, Felix Leiter looks hipper than Bond with his sunglasses, which he places in his outer breast pocket when he removes them. No Felix Leiter other than Jack Lord comes close to having a competing screen presence with Bond, and his cool look has a large part to do with it.

In The Man with the Golden Gun, Roger Moore wears a more adventurous wardrobe than he did in Live and Let Die. For one of the furthest suits from what Sean Connery had established as the classic Bond look, Moore wears a dark olive, double-breasted suit cut by Cyril Castle. The suit has very closely-spaced lighter pinstripes with wider-spaced red chalkstripes. The jacket has six buttons on the front with two to button, double vents, slightly slanted pockets with flaps, and flared link-button cuffs. The trousers have a darted front and flared leg.

The shirt is a white and gold bengal stripe in a twill weave, made by Frank Foster. The shirt has a spread collar, placket front and and two-button cocktail cuffs. The tie is light olive shantung silk, tied in a four-in-hand knot. Even though the outfit is in all earth tones, Moore wears black shoes. But because this suit is worn after dark, black shoes are appropriate, and they don’t clash when not in daylight.

Bond’s Rolex Submariner with a close-up of the striped suit and shirt cloths

Though not in his manner, Oddjob makes a convincing servant in his dress. He wears black lounge, the same type of outfit that Bond wears for his wedding. The black button-three jacket has a high button stance and high lapel notches, which are more flattering to the shorter man that Oddjob is. The jacket has has three-button cuffs and jetted pockets and no vent. The jacket has some fit problems in the chest and shoulders, but a servant wouldn’t likely be wearing a bespoke suit anyway. Oddjob wears a matching five-button waistcoat, and he fastens all the buttons.

The cashmere stripe trousers in grey tones—originally from morning dress—are commonly worn with black lounge. Oddjob’s trousers have double forward pleats and plain hems. His white shirt has a wing collar, front placket and double cuffs. Though the wing collar was once worn with morning dress—like the striped trousers are—it is too formal for black lounge. A wing collar also should not be worn with a four-in-hand tie—though it once was the norm. The inappropriate mixing of formalities is what identifies Oddjob as a servant. His black, military-like derby shoes are also not up to the same formality as black lounge.

Oddjob’s black, flat-crowned bolwer hat—his most famous accessory made by Lock & Co.—is unusual for a servant, but it is the perfect match for his black lounge outfit. Two examples of the hat used in the film have been sold at auction. The first was sold at Christie’s in South Kensington on 17 September 1998 for £62,000. The second was sold by Julien’s Auctions in June 2006 for $33,600.

As part of Live and Let Die promotions, Roger Moore’s photo was taken as Bond in a dinner jacket, yet this outfit didn’t make it to the film. Not wearing a dinner jacket in Live and Let Die was one of the many ways used to distinguish Moore from his predecessors. Cyril Castle made this black dinner jacket in the same six-button double-breasted with two to button style as the double-breasted suit Moore wears at the end of the film. It has softly-padded shoulders, slanted pockets with fancy braided jetting, satin silk peak lapels, and satin silk-covered buttons. The dinner jacket also has Cyril Castle’s flared, link-button cuffs, which are seen on all of the suits in Live and Let Die.

The shirt repeats George Lazenby’s now very dated style with a ruffled front. The lack of such flamboyant clothing that made it into Live and Let Die is more in character for Bond. The shirt is likely made by Turnbull & Asser, in a way to tie Moore’s clothing in with Bond’s already established shirtmaker. It has a spread collar, and its double cuffs have the buttonholes very close to the fold—something which Turnbull & Asser is known for. Moore wears a wide black bow tie and a white handkerchief puffed in his breast pocket.

Brown suede chukka boots in Quantum of Solace

Bond has worn chukka boots in the last four films, from Die Another Day to Skyfall. The classic chukka boot is made in brown suede, and from English makers today they are most often found with Dainite^® rubber studded soles. The standard chukka is a two-eyelet design, but they can just as often be found with three eyelets. Bond usually wears them in brown suede, and in Casino Royale and Skyfall he wears chukkas in calf as well. For the most part, Bond’s chukkas have Dainite® studded rubber soles, except the boots in Die Another Day have either soles of leather or a combination of leather and something else. Chukkas are casual boots, and Bond mostly wears them casually. Roger Moore wore them more formally with his country jackets in The Saint. Daniel Craig went even further with them in Skyfall, wearing them with his grey pick-and-pick suit. But balmoral boots, oxford boots or chelsea boots—like Sean Connery wore in Thunderball—are a better match for the formality of a suit.

Desert boots in Skyfall

In Skyfall, Daniel Craig also wore a variation on the chukka: the desert boot. The desert boot is a chukka—typically suede—with a crepe sole. As the name suggest, they are great to wear in sand. The ankle height prevents sand from getting inside the shoe whilst the crepe soles are very comfortable for walking on sand. Daniel Craig wears his on the beach, but he makes sure they stay dry. On the city pavement crepe soles absorb the dirt off the street and wear out quickly. Craig’s desert boots are light brown suede.