A Guide to James Bond’s Slip-On Shoes and Loafers

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Though not a modern Bond staple, the slip-on shoe is an essential item of the classic James Bond wardrobe. It was the preferred footwear for Ian Fleming’s Bond, who wore black “casuals” or “moccasins” and “abhorred laces”. It is a staple of Roger Moore’s Bond wardrobe, and almost all of his shoes are slip-ons, though all of the film Bonds apart from Daniel Craig have worn slip-on shoes.

Slip-ons are not popular today for dressing up, but they are fashionable for dressing down. Slip-on shoes cover a large range of shoe styles, from pumps and slippers to the more formal elastic-gusset shoes that look hardly different from oxfords to the low-cut casual slip-on shoes known as either loafers, casuals, moccasins or Norwegians. Not all slip-ons are created equal, and Bond does not wear all of his slip-ons the same way. This article breaks down the different styles of James Bond’s slip-on shoes and loafers over the series and how he wears them.

Toe Styles

The toe style is a defining aspects of a shoe, and it often has a greater impact on the formality of a shoe than other factors. When it comes to slip-on shoes, the toe style is what often determines how the shoe can be worn.

Moccasin and Apron Toes

The moccasin toe, or “moc” toe, is the most common type of toe for a slip-on shoe. There are two main variations on this toe: the apron toe and the proper moccasin toe. The apron toe is often called a moccasin toe, and it is indeed a variation on the style. The apron toe usually has a separate piece of leather—the “apron” or, as John Lobb St James’s calls it, “lake”—sewn on top of the vamp, but the apron does not extend to the end of the toe. This allows the shoe to have a curved or chiselled toe in front of the apron for an elegant look. Sometimes the look of an apron is simulated purely with stitching instead of a separate piece. Some apron toes have a seam at the toe, which is called a “split toe”, “Norwegian toe” or “Algonquin toe”. This type of toe is more commonly found on Norwegian-style derby shoes.

Two Gucci bit loafers: a moccasin toe on the left and an apron toe on the right.

A true moccasin toe shoe has piece of leather that extends from the vamp to the end of the toe that is sewn, often with a puckered seam, to a separate piece of leather that wraps around the front and sides of the shoe. This type of moccasin is a casual shoe and does not dress up well, while the apron-toe shoe can be dressed up or down more easily. The proper mocassin toe loafer should not be worn with a suit. While an apron toe slip-on can be dressed up to that level, and often has been done since the middle of the 20th Century, it’s considered by many traditionalists to be too informal for a suit.

Plain Toe

A plain toe has one piece of leather from the vamp of the shoe to the toe, giving the shoe a clean and elegant look. Derby and monk shoes are the most common styles of shoes with plain toes, but slip-on shoes can also have them. Plain toe slip-on shoes are usually the most formal of slip-ons, espcially when they have a higher profile.

John Lobb St James’s elastic on instep slip-on shoe with a plain toe, a very dressy design

Cap Toe

A cap toe has piece of leather on top of the toe than extends from the sole to sole across the toe, reinforcing the toe. This is a formal style like the plain toe but is rarely found on slip-on shoes. When it is, the slip-on shoe is usually a more formal shoe that is appropriate to wear with a suit.

The Anthony Cleverley Hague II semi-brogue cap-toe slip-on shoe from George Cleverley, an English shoemaker known for their dressier slip-ons

Bicycle Toe

The bicycle toe shoe has a separate vamp that extends all the way to the front of the shoe, while the quarters fill in the sides. This is often considered the least elegant style of toe, as it is typically done with a very square toe, and the construction of the shoe emphasises a squared last. The toe got its name based on its resemblance to a bicycle toe clip. Roger Moore wears burgundy crocodile skin bicycle toe loafers in Live and Let Die in the crocodile jumping scene. He also wears black square bicycle-toe loafers with an unusual vamp detail with his checked sports coat in The Man with the Golden Gun.

Roger Moore wears burgundy crocodile shoes with a bicycle toe in Live and Let Die

Types of Slip-on Shoes

Penny Loafers

Roger Moore’s penny loafers in For Your Eyes Only

The penny loafer is the most common style of slip-on shoe. Over the vamp it has a strap or band with a slot where some Americans once placed a penny. Sometimes the strap is a full strap that extends from sole-to-sole and is used on dressier loafers, but most typically the strap is only placed over the top of the shoe. Sometimes the ends of the strap are rolled and sewn together, which is known as a “beefroll” and makes the shoes more casual. Penny loafers may have either a dressier apron toe or a casual moccasin toe. Typically the heel is low.

Roger Moore’s penny loafers in Octopussy

This is likely the kind of shoe that Ian Fleming specified for James Bond to wear in his books when he wrote in Moonraker, “well-polished black moccasin shoes”, or in On Her Majesty’s Secret Service, “black casual shoes (he abhorred shoe-laces)”. The penny loafer style best fits the “moccasin” description, though his Bond possibly could have worn a dressier slip-on style. James Bond in the films wore this style of shoe in the 1980s. Roger Moore wears apron-toe penny loafers in his three 1980s Bond films. This kind of loafer was very popular to wear with suits in the 1980s. His examples have a narrower strap than most.

Timothy Dalton’s moccasins in Licence to Kill

Timothy Dalton wears traditional penny loafers with an apron toe in The Living Daylights in brown with his gun club check sports coat and his tan suit. In Licence to Kill, Dalton wears hand-stitched moccasin-toe penny loafers with a strap over the top and a very low vamp that is characteristic of the 1980s. Because these shoes have moccasin toes, they are traditionally considered much too casual to wear with a suit, but that is how he wears them. The low vamp that shows off more sock makes the shoe dressier because it is a less utilitarian shoe and resembles a formal pump shoe in this way, but this added formality is incongruous with the puckered moccasin toe.

Venetian Loafers

Pierce Brosnan wearing tan Venetian loafers with his linen suit in Die Another Day

Venetian loafers are a casual loafer style with a hand-stitched moccasin toe and no strap. Like penny loafers, Venetian loafers also have a low heel. The Venetian loafer has often been butchered in recent years by making it on a square last with an apron toe and side gussets in an attempt to make it a more formal style, but the shoe’s charm comes from it being a simple, casual shoe.

Pierce Brosnan’s Venetian loafers from Die Another Day as sold at Heritage Auctions

Pierce Brosnan dresses down his linen suit Die Another Day with tan Venetian loafers from Italian shoe brand Stemar. Brosnan’s shoes have perforated sides so they wear cool when worn sockless. A signed pair were sold at Heritage Auctions.

Sean Connery and Daniela Bianchi during the filming of From Russia with Love. Sean Connery is wearing a suit that he wore in Dr. No with his own Venetian loafers.

Sean Connery was a fan of Venetian loafers in his personal life and can be seen wearing during the filming of From Russia with Love, though he did not wear them in the film.

Tassel Loafers

Roger Moore wearing tassel loafers with his navy suit and navy chesterfield coat in Live and Let Die

Tassel loafers do not come to mind when thinking of Bondian footwear, but they make up Roger Moore’s formal shoe wardrobe in his first Bond film Live and Let Die. This style of loafer became popular in America in the middle of the 20th Century and is most associated with American style. As James Bond spends much of the film in America, and he was forced to Americanise his wardrobe in Ian Fleming’s original novel, this shoe is a fitting tribute to Fleming. Otherwise it isn’t the kind of shoe that Bond would ordinarily wear. Ian Fleming hated laces, and he most certainly would have despised the useless tassel decorations.

A classic stitched-apron-toe tassel loafer: the Crockett & Jones Cavendish

The shoe has a pair of tassels hanging from the middle of the vamp with decorative laces woven though holes at the top of the quarters. This is a dressier style of loafer that is traditionally worn with suits or jackets and trousers, and it usually has an apron toe but sometimes may have a plain toe, a cap toe or a wing tip in an effort to look more like a traditional business shoe. There are no clear close-up photos of Moore’s tassel loafers, but it appears that they may have plain toes.

Horse Bit Loafers

The classic Gucci horse bit moccasin-toe loafer

In 1953, Gucci premiere their quintessential moccasin with a horse bit detail set into a strap over the vamp. What is a bit? A bit is a metal horse tack that is placed inside of the horse’s mouth and used to communicate with the horse. Because the bit is an equestrian detail, it makes the shoe rather sporty and is a fun detail for a casual loafer. Gucci also put this detail on dressier apron-toe loafers. In all of his 1970s Bond films, Roger Moore wears bit loafers from both Gucci and Ferragamo. Thanks to 1970s trends, Moore’s loafers have higher heels than loafers typically have.

Roger Moore wears Bond’s first bit loafers on screen with this outfit in Live and Let Die

The bit loafer first appears in Live and Let Die. While Roger Moore wears it in many production stills, paired with the navy leisure suit, in the film Moore only wears it with his black shirt and tan trousers. This variant has an apron toe and a bit with the two ends connected by a round Gucci emblem in the middle. The same bit appears on a black moccasin-toe shoe that Moore wears with his navy blazer in The Spy Who Loved Me. Moore’s shoes are black.

Roger Moore’s classic Gucci bit loafers in The Man with the Golden Gun

In The Man with the Golden Gun, Moore wears the classic 1953-style Gucci moccasin style bit loafer in dark brown with his casual cream outfit. Though some people wear this shoe with a suit, these are ultimately casual shoes and work best in this casual manner.

Roger Moore wearing Gucci bit loafers with the classic green and red web detail in The Spy Who Loved Me

In The Spy Who Loved Me, Moore wears the Gucci moccasin-toe loafers in tan suede with his tan cotton sports coat and stone trousers. These shoes have Gucci’s classic green and red web under the bit. The web makes these shoes even more casual than in shoes without.

Roger Moore’s Ferragamo side-bit loafers in The Man with the Golden Gun

With his suits in The Man with the Golden Gun he wears a variant known as the side bit loafer, which has a small bit detail on the outer side of the strap. Side bits are found on both very casual loafers as well as the dressier variant that Moore wears, but the small metal detail here doesn’t distract on screen from the dressier outfits in the film. Moore’s shoes are black or dark brown and have an apron toe.

Roger Moore’s patent leather side-bit loafers in The Spy Who Loved Me

With his dinner suit in The Spy Who Loved Me he wears black patent leather apron-toe side-bit loafers, with the strap sliding through an unusually-shaped metal piece. These shoes are very unorthodox for black tie, but being in patent leather with a decorative element helps make them more formal.

Roger Moore’s stuntman Martin Grace in Moonraker wearing Roger Moore’s outfit in Venice, including his Ferragamo bit loafers

For Moonraker, Moore wears Ferragamo bit loafers. Moore’s everyday formal shoes in the film are apron-toe loafers from Ferragamo with a very narrow and subtle bit. They have a rather squared toe and look chunky from the front, but the extra visual weight they have balances the flared trousers. He wears them with his suits, his blazers and even his sporty all-black outfit for sneaking around at night, when neither the bit’s reflective properties nor the jangling sound it makes aren’t particularly helpful.

Roger Moore’s Ferragamo bit loafers in Moonraker

Dressier Slip-Ons

Though Sean Connery wears short slip-on demi-boots in Goldfinger, in Thunderball he wears Bond’s first slip-on shoes on screen that aren’t espadrilles. Briefly seen in Thunderball when he washes his ankle in a sink at the Junkanoo are black plain-toe slip-ons made in three pieces: the toe and vamp make up one piece while the quarters make up the other two. This shoe is most likely an English-slip on, based on the style. These shoes are low cut on the sides like a loafer, but they are more formal than most loafers due to their plain toe.

Sean Connery wearing dressier loafers in Thunderball

In You Only Live Twice we see a similar style of slip-on in black grain leather, but this shoe has higher sides and has elastic over the instep of the foot under the vamp. John Lobb St James’s specialises in bespoke shoes of this style. Grain leather is not quite formal enough for a worsted suit, but this style in black calf would be perfect to wear with a suit. Bond has multiple pairs of this shoe in You Only Live Twice because after removing them at Dikko Henderson’s door, he had to run after his killer and had no time to fetch his shoes. He instead is forced to wear this assassin’s ugly black-and-white slip-on shoes.

Sean Connery wearing elastic instep slip-on shoes in You Only Live Twice

Ian Fleming himself wore the elastic instep type of slip-on, and it is possible that this is the kind of shoe he meant when describing “moccasins” or “casuals”, even though this dressier style would not be properly described as either. This kind of shoe is much more appropriate to wear with a suit than a proper moccasin-toed shoe is.

Another similarly formal slip-on shoe that English shoemakers do is the side-gusset slip-on. This shoe has elastic gussets between the vamp and the quarters of the shoe to give it ease when putting it on and taking it off. George Cleverley specialises in this style. George Lazenby wears such a shoe in On Her Majesty’s Secret Service in black calf with his wedding outfit and in black patent leather with his evening wear, which resemble Prince Albert (smoking) slippers because of the plain toe. Patent leather slippers are a traditional footwear choice for black tie. Lazenby’s shoe has a high vamp but low quarters, combining the formality of a higher shoe with the comfort of a slipper or loafer. The toe is chiselled and a little square.

George Lazenby’s elastic-gusset slip-on shoes in On Her Majesty’s Secret Service, on the left in patent leather with his dinner suit and on the right in black calf with his black lounge wedding attire

Also amongst Bond’s most formal slip-on shoes are the cap-toe loafers from Ferragamo that Roger Moore wears with his dinner suit in Moonraker. These shoes sit low on the sides like a loafer, and they have a plain, solid strap over the top. These shoes are made of calf leather rather than the usual patent leather for black tie, but for a man like Roger Moore who preferred to wear loafers with everything they are an unorthodox yet not entirely inappropriate alternative to the traditional patent leather oxfords or pumps. Like an oxford they have a plain toe, like a pump they slip on, and the decorative strap takes the place of the pump’s decorative bow. It’s a stretch, but it’s James Bond.

Roger Moore’s Ferragamo slip-on shoes with his dinner suit in Moonraker

Christie’s sold these shoes on 24 November 2009 for £3,000, but Roger Moore incorrectly stated that they were from The Spy Who Loved Me instead of Moonraker. But one thing Moore got right was that he did indeed kick Jaws in these shoes.

Roger Moore’s Ferragamo shoes from Christie’s

Timothy Dalton wears a shoe for black tie in The Living Daylights that is more of a proper cross between the pump, the Albert slipper and the loafer. Many find the classic evening pump either too old-fashioned or its delicate shape and bow too effeminate. Dalton’s black patent leather evening shoe updates the pump to a shape more familiar to the average man while maintaining the traits that make it an appropriate evening shoe.

Timothy Dalton’s patent leather slip-ons in The Living Daylights

Dalton’s shoe starts off right by being in the traditional evening shoe material, black patent leather. Though pumps, slippers and loafers are all slip-on shoes, the pump has a simpler shape and a very low vamp that shows off a large amount of foot, or rather silk evening hose. Dalton’s shoe has a slipper shape that is low on the sides but has a higher vamp for a more modern and familiar look than the pump. The toe is plain like on a pump or a slipper to give the shoe a more formal look. While the standard evening pump has a silk grosgrain bow, Dalton’s shoe replaces it with a decorative silk strap over the vamp, likely in silk satin. The strap detail comes from the loafer but the silk material evokes the pump. This shoe is not the traditional evening pump, slipper or oxford, but it keeps within the spirit of the traditional black tie shoes. James Bond has often updated his black tie clothing from the standards established in the first half of the 20th Century, but with his understanding of black tie conventions he is able to bend the rules in successful ways.

Black patent leather slip-on shoes from Ferragamo that are similar to Timothy Dalton’s evening shoes in The Living Daylights

Low Monk Shoes

Two pairs of George Lazenby’s low monk shoes in On Her Majesty’s Secret Service

In On Her Majesty’s Secret Service, George Lazenby wears an unusual type of monk strap shoe that resembles a loafer more than it does a typical monk shoe. It has a strap and buckle, but it has a slightly lower vamp than a monk shoe with the strap placed much lower over the vamp, and the quarters are lower like a loafer’s. The shoe has the profile of a loafer, and it looks as if it can be put it on without undoing the buckle, so they have been included here amongst James Bond’s slip-ons. Lazenby wears this type of shoe in black calf, cream calf and brown suede with his suits and his casual golf wear.

Special thanks to Thunderballs.org for sourcing many of the stills used here. We otherwise would not have been able to see some of these shoes so well, if at all.

31 COMMENTS

  1. I can’t say I like moccasins at all. They simply remind me too much of my father’s wool-lined moccasin slippers, so I can’t take them seriously when seen in the wild. Especially with a suit!

    I do really like Lazenby’s monk strap slip on and particularly Dalton’s updated pumps. I’m one who sees opera pumps as being completely outdated and replaced with the oxford for black tie, but this is a great way to bridge that gap of traditional and modern. I’d happily wear them!

  2. Excellent, comprehensive article. Thanks for doing this. I never appreciated how stylish Dalton’s black tie footwear was in TLD. A rare sartorial score for Dalton’s Bond!

  3. Many thanks for this Matt, I’ve spent countless hours zooming in on Moore’s outfit to get a better look at his slip – ons, so it’s nice to see the full bond collection in one place. I tend to only wear loafers with my formalwear these days, so it’s useful to see an article demonstrating the appropriate level of formality for loafers when worn with a suit.

  4. Never knew that James Bond has worn so many slip on/loafers throughout the series. Truly an eye opener! I love slip-on shoes but it’s very difficult to find ready-to-wear ones that fit well. Lace-ups are much more likely to fit alright.

  5. I have wide feet with very high arches, so I can never find slip on shoes that fit me. I also avoid moccasin toed shoes at all, because they’re what my father wore pretty much every day, as tassel loafers until about 15 years ago and then as driving mocs after that, and I suppose I associate them with a style that’s old fashioned, but not necessarily classic.

    • Interesting view. I associate driving mocs with modern fashion trends, and young people complaining about how they wore out after only a few weeks of walking on city streets.

  6. I currently only own one pair of dressy shoes, and they’re black leather (I think calfskin) Venetian loafers from Florsheim. The black lends them a formal look, but I also feel they’re casual enough and comfortable enough for almost any occasion. I agree very much with Flemming as far as laces are concerned. Slip-ons are comfy and it takes only a few seconds and no bench to slide them on and off, while laces have to be tied whenever shoes are put on or taken off. I also think the pain, laceless front has a more elegant look.

  7. Interesting. But I have to say – penny loafers WERE popular. I wore them for years (my one Peter Pan clothing choice) and I can’t find them anymore.

    When Payless went out of business, I ended up buying two pairs of loafers horse bit loafers – the closet I could find to penny loafers.

    At least this has been my experience over the last couple of years.

    • most shoe makers have some sort of penny loafer, although finding them in a big box store is probably pretty unusual.

      i also abhor laces, so i have a lot of slip ons, the newest is a Bass Weeguns, period correct, and quite comfortable. possibility that the literary bond had a pair in ‘Live and Let Die’. the other possibility would be Aldens

      “Two pairs of hand stitched and very comfortable black moccasin ‘casuals’ “

    • I have never heard of this before. Proper Venetian loafers are casual shoes and in no form are they traditional shoes for black tie. The dress slipper is similar and appropriate for black tie.

      • I’m guessing the guy behind that blog would probably consider what you’re calling ‘gusset slip-on shoes’ as ‘Venetian loafers,’ since on the same blog he says black tie patent leather Venetians are a James Bond look.

  8. To be fair I personally have a liking to wear loafers almost anytime much like Sir Roger Moore did. I admit that slip-ons are much more comfartable with my feet than a laced shoe is. More often than not I wear it casually and formally (though at most formal my grey pick-and-pick suit)

    On the topic of wearing slip ons with formal/semi-formal wear, would black slip-ons (such as a pair of black penny loafers) work well with the formality level of a navy blazer combo with grey dress trousers and/or khaki slacks?

    • @Matt Spaiser – Do you know if Moore’s slip-ons are ready-to-wear or if they were made for him? I recently read “The Loved One” by Evelyn Waugh, and in the book a Britisher in LA contemptuously says one of his fellow Britishers went native when he started wearing ready-to-wear shoes and a belt instead of braces, so I assume that MtM/bespoke shoes were the norm in Britain at least until the 1950s.

      • I think Moore’s slip-ons are ready-to-wear. I’m not aware of Gucci and Ferragamo doing bespoke shoes back then, though he has shoes from other makers too. Some could be bespoke.

    • Ivan B. like yourself, I wear slip on shoes (Ferragamo, of courses) with both my formal suits, through blazer/sports jacket and trousers and with more casual outfits. I’ve never had much problem with making them work either. Why would a well polished black penny or horsebit loafer, for example, not work just as well as a well polished lace up shoe with a well cut suit? A certain amount of this comes down to subjectivity though a horse bit loafer, for example, won’t look right with black tie. Roger just about got away with the shoes in TSWLM because they were patent leather but without the side bit would’ve been a bit better. But a minor quibble….

      Matt, I have had a couple of pairs of Ferragamo shoes (I’m wearing them today) in a style which has a side bit and apron toe but after the apron to the sole of the shoe there’s a split in the leather. I assume this would be termed a split-apron loafer or the like?

      The only loafer I was never that fond of is the tassel variety. I remember these being very popular in the 1980s and often had a kiltie too which was horrible. I never knew that Moore wore a loafer with tassel as I’d never seen the LALD shoes so closely. The tassel seem small ans subtle but would’ve been better, imo, without.

    • I must agree with you there David, because I am a huge fan of wearing slip on shoes. I admit that it was the influence of Sir Roger and the Japanese to wear easy removal shoes such as slip on shoes.

  9. In Thunderball Bond wears black slip ons with broad side gussets along with his brown suit in M’s office. They are different from the ones posted above as they are almost like low cut Chelsea boots with wide gores.

      • Yeah I wondered why you didn’t mention the Thunderball footwear here. I don’t recall the exact details but I thought they may have qualified as I thought they were low enough to be considered shoes. As I kid in the seventies I remember having a couple of pairs of ‘Clark’s Commando’ shoes which had visible side cores like Chelsea boots but were definitely low enough to be considered shoes not boots. That style seems to have completely fallen out of favour. I thought Connery wore similar in Thunderball but your knowledge of greater detail may prove them to be more boot(ies) than shoes.

  10. Excellent article. I wish plain-toe slip-ons were as easy to find as penny loafers. I haven’t seen them in the UK outside Lobb and Crockett & Jones (both a little outside my price range . . .)

    Perhaps you could do a (00)7 James Bond shoes and boots?

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