When it comes to discussing James Bond on the screen, many will point to Sir Sean Connery as being the definitive version character wise. Many would also reasonably argue that he’s definitive in what he wears as well. He perhaps came the closest to what Ian Fleming set forth in the books style wise, with the mostly solid colour suits (some simple plaids and stripes thrown in for good measure), solid ties, and solid shirts. Thankfully, the short sleeved shirts with lounge suits were not replicated. Instead, we got unfussy, but stylish cocktail cuffs and the addition of a neatly folded white linen pocket square -- a popular menswear touch in the 1960s. Essentially, he was all about simple elegance apart from some questionable choices in his last movie. It is also his wardrobe that serves as a template for Daniel Craig’s tailored clothing in Quantum of Solace onward.

What’s not discussed so often is his choice of footwear, which follows the same prescription for simple elegance. Many of these dress shoes and boots were probably made bespoke by John Lobb Ltd. They have definitely been confirmed to have made most of the shoes in Diamonds are Forever. They should not be confused with John Lobb of Paris, the secondary location opened in 1900 which was later acquired by Hermès in 1976. However, many could have just as well been made by other traditional English shoemakers since these styles are not uncommon with them.

Starting with Dr No, we’re introduced to a secret agent who has a taste for the finer things in life. Well-fitting and high quality clothes, health food for breakfast, strong drinks -- whether it’s “very black” coffee or vodka martinis, and five star hotels. We also get a small taste of his footwear choices. Introduced in his perfectly tailored dinner suit -- sans cummerbund or braces per his unfussy dressing habits -- he wears what appear to be a well-shined, black calf pair of cap toe oxfords. Oxfords have closed lacing at the throat, which lends a more streamlined appearance, and are thus the best choice for black tie. They could be patent leather but it’s hard to tell.

A plain toe goes well with the elegance of a dinner jacket, but well-made cap toes with a sleek last, narrow waist, and single row of stitching as these have are also perfectly acceptable. This makes them flexible for both informal and semi-formal attire. Strangely, for something considered a foundational item of a professional wardrobe, Bond would not wear black oxford cap toes again until nine years later in Diamonds are Forever, but with the addition of a heel counter. This is usually only seen on brogues, but was perhaps added for extra durability in the elevator fight scene they are featured. This time it’s worn with a business suit instead of a dinner suit. In this film he also wears the most traditional style of shoe for black tie, the Oxford – Plain in black patent leather with a white dinner jacket and black dinner suit (from a distance).

The rest of his tailored clothing in Dr No, including the navy blazer, is worn with a black cap toe V-front derbys. Apparently, he packed light for his mission in Jamaica. (In reality, there was a tight costuming budget so they probably reused as much as they could.) V-fronts are named for the striking pointed shape of the quarters where the laces are held, forming an upside-down “V”. It’s worth noting that Ian Fleming’s character “abhorred” laces. Sean Connery’s James Bond, on the other hand, seems to be quite a fan of the V-fronts, as he’d go on to wear them in four other movies with or without cap toes, with two or three eyelets. Most often in black calf leather for grey and blue business suits, but also in brown suede for his brown tweed hacking jacket and light brown calf leather for a cream linen suit. It’s a surprisingly versatile style. In brown, one can even wear it with jeans and chinos.

Now, contrary to a lot of online menswear forum groupthink, there is absolutely no rule against derbys with business suits. Additionally, the quarter shape, limited number of eyelets, sleek last, and single sole which Bond prefers go much better with suits than derbys with short quarters, five eyelets, a heavy profile, and double sole like the Leeds from Allen Edmonds. The latter style, known as a plain toe blucher, is more common with American shoemakers such as them and Alden.

V-front plain toes can also look good with black tie due to their pared-down look, especially with only two eyelets. Connery demonstrates this wearing a pair in black patent leather with a white dinner jacket and black dinner suit (close up) for his final movie as James Bond. It’s unknown why two different pairs of patent leather shoes were used for his dinner suits in that movie.

Like silk knitted ties, which Sean Connery also began wearing in Goldfinger, his slip-ons are inspired by Ian Fleming’s writing. However, the costumers wisely chose more dashing styles than the black moccasins, or casuals, worn by the book Bond with his suits. Hand-stitched moccasin toes, such as on Norwegians a.k.a. penny loafers, should only be worn with casual attire. He begins by wearing a shoe that has side elastic -- much like a Chelsea boot -- with his iconic white dinner jacket. A short boot version of the same thing is also worn with a couple of lounge suits including the similarly iconic three-piece glen plaid (when it isn’t worn with two-eyelet V-fronts). The elastic gore at the sides makes them easy to slip on and off, but are they appropriate for black tie?

There is also a style that has elastic hidden under the vamp to keep cleaner lines, referred to as Elastic On Instep by John Lobb. He wears these with grey and blue lounge suits in smooth calf and grain leather, both black. The latter is an odd choice since grain leather looks more at home, dyed brown, on casual shoes. A short boot variation which barely covers the ankle is seen in Thunderball, also in black calf. Both styles of slip-on have an appealing minimalism that would probably speak to the literary Bond if he wanted something more refined than his moccasins.

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Connery-Bond’s style undergoes a slight metamorphosis in Diamonds are Forever after the more fashion-forward styles worn by George Lazenby, who declined to return after On Her Majesty’s Secret Service. Connery kept the same tailor as before, Anthony Sinclair, for his final film. The suits were now updated to have wider lapels, slanted pockets, deeper vents, and a cleaner chest. Pleats and turn-ups were also completely absent from the trousers for the first time. Camp shirts made of toweling, tweed half-Norfolk coats with large collar points, and dinner suits inspired by the Peacock Revolution would also make an appearance. Similarly, the shoes and boots would need a slight facelift to keep up with the times. This change of style was a bit controversial, especially that ill-chosen pink tie, but it did at least serve as a bridge to Roger Moore’s dandy-ish take on the character.

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Besides the oxfords and V-fronts mentioned earlier, he also wears the Brogue V-Front for the first time. These have three eyelets and V-front lacing but with the addition of broguing, wingtips, and a heel counter. It’s a little more fussy than we typically see Connery’s Bond wearing, but the last shape and lacing style makes this a sleeker choice than the typical American, full brogue wingtips. These are worn with three lounge suits but also, unfortunately, a velvet dinner jacket.

The boots also have more personality -- and height -- than before, with Bond donning a couple of styles with straps. Strap boots for men are not a recent innovation, but they have seen a bit of a renaissance in the last few years. Connery wears both the Strap Hilo Boot and Strap Jodhpur Boot. The Hilo is worn in both black suede (when riding a bike) with a grey wool suit and light brown calf with a cream linen suit and checked tweed jacket. Black suede is an odd choice considering he was just wearing the Brogue V-Front indoors with the same suit. Much like the aforementioned black grain leather, it’s also an unusual colour for a casual leather type. The Strap Jodhpur in black calf is a more extravagant style with the way the strap wraps around the ankle and crosses itself. This style from Brooks Brothers and Beckett Simonon are a good, if not exact, match. This style lends itself well to a sporty outfit, in this case a brown half-Norfolk jacket, black trousers, and a black polo jumper. Some think boots with straps around the ankle are too flashy with suits. However, it’s something that will be hidden under the trouser hem while standing up. Do you agree?

All in all, we can say that while Connery may have been the most conservative Bond, his shoes and boots were hardly boring. Much like the clothing subtly stands out from all the grey and blue business suits of his time, there are a number of small details that give them character in the sea of other black (and brown) shoes. Namely, a sleek last, bespoke fit, and the method of lacing, straps, or slip-on elastic. What are your favourite shoes and boots from Sean Connery as James Bond?

Giselle GAUTHIER

Instagram: @nouveauvintagegiselle

Giselle is a menswear expert and freelance writer who gained an interest in dressing well upon re-watching James Bond movies, researching what makes him so stylish, and later engaging with others in online spaces to learn more. She has written about tailored clothing for over a decade through her blog, Nouveau Vintage, after being inspired by others to share her passion.

Matt Spaiser is a graphic designer located in New York. After years of research, he founded The Suits of James Bond in 2010, creating the ultimate resource for James Bond style and the first catalogue of all of 007’s outfits. If you have any questions about James Bond’s clothing feel free to contact Matt.

The Shoes of James Bond: Sean Connery's Simple Elegance