The brown suede shoes that Sean Connery wears with his hacking jacket and cavalry twill trousers in Goldfinger and Thunderball are something people often ask me about. Thy are 2-eyelet derby shoes in what essentially looks like a short chukka. The soles are dark brown rubber. The suede uppers, rubber soles and thicker laces make these more casual—but also more versatile—shoes. They work well with informal country wear like in Bond’s case, but they could just as easily be at home with a pair of jeans. They have a slight edge of formality over chukka boots, which allows them to be dressed up a little more whilst at the same time they can still be relatively casual shoes.
My best approximation of the style of this shoe.
Daniel Craig wears very similar shoes with his grey linen suit in Casino Royale.
Ian Fleming specified in Moonraker that Bond wears “well-polished black moccasin shoes.” Timothy Dalton’s black slip-on shoes in Licence to Kill probably started out well-polished but quickly get dirty. Dalton’s shoes have a casual, handsewn moccasin toe, which makes them not the best choice of slip-ons for a suit, but slip-ons traditionally aren’t worn with suits anyway. By the 1980s, slip-ons were an acceptable choice of shoes with a suit, and Dalton’s slip-ons have the characteristic 1980s low vamp. The low vamp shoe allows the dandy to show off his socks, though Dalton chooses to wear unstylish black with his. Blue socks to match his suit would have been a better choice. Though the shoes look a little dated now, they appropriately fit Dalton’s idea of bringing Bond closer to the literary source. With a higher vamp these shoes would be stylish in any era.
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.
Around the corner from Pall Mall on St James’s Street in the London district of St James’s are two stores associated with the first Bond films. The first is Lock & Co. Hatters, where Sean Connery got his trilby in Dr. No. The closest hat they have to what Connery wore is the Sandown model, and no matter what colour it looks in the film they insist it was brown. The hat in the shop did not look to be the same brown as in Dr. No, but on-screen colours can be deceiving. Lock & Co. is known for it’s trilby hats, “coke” (bowler) hats and vintage, refurbished silk top hats, which are nobody is able to produce anymore. They also have a large selection of American-style fedoras and tweed hats and caps.
To find out more visit LockHatters.co.uk
The other St James’s Street shop is John Lobb Ltd., a family-run bespoke shoemaker to royalty and is rumoured to have made Sean Connery’s shoes for the early Bond films. They do the work on the premises, and the shop is like a museum. Craftsmen work right in the front of the shop, using old-fashioned methods and working with vintage machines as well as their hands. They have separate people who each specialise in their own craft, whether it be last-making, lasting, stitching, dyeing, etc.
The wall to the right when you walk in is lined with countless unique examples of the shoes they produce, but they can make just about any style. Though most people would never consider spending so much money on bespoke shoes (their price is in line with the most expensive of bespoke suits), it’s a wonderful place to visit just to see one of the few makers left who do it the old way. John Lobb Ltd. is not to be confused with John Lobb Paris, which has been owned by Hermes since 1976.
You can see examples of John Lobb Ltd.’s work at JohnLobbLtd.co.uk
Black moccasins in Moonraker
Throughout the 1970s, Roger Moore often wore horsebit moccasins. The style was first created by Gucci in the 1960s and reached its highest popularity in the 1980s. Moore’s examples are most likely from Gucci. Whilst he did wear shoes by Ferragamo, it is unknown if any of his bit moccasins came from there. But by the 1980s Moore had given up horsebits for more conservative slip-ons. Moore wears his horsebit moccasins in black, dark brown, light brown and tobacco suede with his suits and sports coats. His shoes have leather soles and a taller heel.
Tobacco suede moccasins in The Spy Who Loved Me
Fleming’s Bond was known for wearing slip-ons with just about anything, and that aspect carried over to Moore’s Bond. However, Fleming and his James Bond character would likely dismiss the shiny horsebit as too flashy and vulgar if they ever saw such a shoe.
Light brown moccasins in The Spy Who Loved Me
In Thunderball, Bond wears light blue canvas slip-ons with his outfit of a rose shirt and light blue swimming trunks after a swim. These casual shoes are appropriate for the beach or poolside, and they breathe well in hot weather whilst keeping the toes covered. The shoes have double elastic gussets.
Two weeks ago I covered George Lazenby’s poorly received brown and orange golf clothing, but the shoes worn with that outfit will be discussed in more detail here today. The slip-ons are made on a narrow, elongated last with a slightly pointed toe, a fashionable style in the 1960s. The shoes are made in brown suede, slightly darker than typical tobacco-coloured suede. They have a plain toe and a high vamp with a strap across the vamp with a buckle, though I wouldn’t consider these to be monk shoes. Slip-ons are usually made with a lower vamp so they are easier to put on and take off, though these have a higher vamp than most. The higher vamp and plain toe visually elongate the shoe, emphasizing the already long last. A shoe like this will be very difficult to find ready-made, as it’s in between a slip-on and a monk. Nevertheless it’s an elegant pair of shoes that is the highlight of Bond’s golf outfit in On Her Majesty’s Secret Service.
Roger Moore always wore slip-ons with his suits, as practised by the literary James Bond. Slip-ons are traditionally too casual to wear with a city suit, though it was popular to wear them in that fashion in the 1980s. Moore left behind the bit loafers in the 1970s and for the 1980s wore a more conservative style. In For Your Eyes Only he wears a black slip-on with an apron front and strap. The rest of the outfit can be seen here.