James Bond of 2025

[classless]

I've actually researched the issue of these loafers a lot as Bond is one of my earliest and biggest style influences. While I agree with you about Fleming's Bond not being a dandy, I think he would go bespoke. The books are very clear that he strongly subscribes to the old English reverse snobbery of buying only a few things of the highest quality and then wearing them until they are threads or fall apart. So I think Bond would be a bespoke guy, although like Fleming definitely off-Row and looking for a good value.

The novels also indicate that Bond's loafers have bespoke details like throwing knives concealed in the heel. Old Bond scholars like Kingsley Amis were of the opinion that Bond's intended shoemaker was Nicholas Tuczek given the reference to his signature "square toe" by Fleming in the letter and the fact that Tuczek's shop was next door neighbours with a bladesmith.

Fleming also tended to give Bond a lot of his own style quirks like the preference for short sleeve shirts (Fleming worked as a journalist and hated getting newspaper ink on his shirt cuffs. Also lived half the year in Jamaica.). Based on the types of apron toe penny loafers Fleming wore, my best guess for what Bond's loafers looked like is this vintage Lobb pair (except in black):

Fleming can be seen in photos wearing loafers and other slip-ons with a similar soft square toe shape.

Now if you are connecting the dots between all of this research and my recent commission of Tuczek-inspired soft square toed penny loafers, you would be very correct. Also, until they are ready, I am wearing my RTW John Lobb Lopezes. 😉

Great info, look forward to seeing the finished product. So the original Bond's go-to shoes might be along the lines of Cleverley's George model. Do you think this would still be the choice of a Bond who was born in 1990?

 

[ForwardPleats]

Great info, look forward to seeing the finished product. So the original Bond's go-to shoes might be along the lines of Cleverley's George model. Do you think this would still be the choice of a Bond who was born in 1990?

I wouldn't say they would be along the lines of Cleverley's George model. The George has a pretty elongated/pointy toe that I don't see as very Bondian. They are also unlined, which doesn't make for a good long-term business shoe.

Bond in the Fleming novels was 37, so in 2025, would be born in 1988 actually. As a huge literary Bond fan born in 1988, the closest RTW shoes I would say get the closest are:

1. Edward Green Pimlico (sadly currently being changed over to a round toe last for 2025):

2. Cheaney Saxon

In terms of the rest of Bond's ensemble, I still think a lightweight single breasted solid navy twill suit in a traditional English cut would be Bond's go-to business attire as a government employee. Something like Dege & Skinner's RTW offerings would get you pretty close at a reasonable price point:

https://dege-skinner.co.uk/product/navy-blue-single-breasted-two-piece-suit/
Single breasted, notch lapels, forward pleated trousers with side adjusters, and turn-ups/cuffs. I think Fleming would replace the short sleeve shirts with long sleeves since getting ink on the cuffs is no longer a hazard of working in an office. The black knit silk tie would continue to be timeless neckwear and along with the loafers would give Bond the same intended air of comfort and casualness.

Although starting with Connery, the cinematic Bond wore more grey suits, I think navy blue is a better fit for the character since it evokes his Naval background and also greatly complements his blue eyes (which is why Lindy Heming dressed the blue eyes Daniel Craig in a lot of navy in Casino Royale).

A great source for more information on this topic is Matt Spaiser's brilliant blog, Bond Suits:
https://www.bondsuits.com/category/literary-bond/

 

[Thin White Duke]

The EGs come closer than the Cheaney for me.
There may be some conflation in the above discussion of bespoke suits and bespoke shoes. In Fleming’s era well to do London civil servants like he and Bond were patrons of bespoke tailors but my instinct tells me that neither would have been regular patrons of bespoke shoemakers. The Lobb Lopez (likely not around in that era) is a beautiful RTW black Mocassin loafer and comes very close to how I’d picture book Bond dressing his feet.

If we’re talking of teleporting Bond to the present day those Lopez still wouldn’t look too far out of place. Unfortunately a navy suit with black tie would be eye catching in all but the most conservative business dress working environments - not a good attribute for a secret agent - so it will be interesting to see how they clothe our hero in the next round of films.

It was getting increasingly difficult to come up with a scenario in the films for Bond to get into his signature tuxedo. Before long it will be difficult to clothe him in anything above a hoody, sweatpants and crocs if he’s to fit in with any urban scenery.

 

[ForwardPleats]

The EGs come closer than the Cheaney for me.
There may be some conflation in the above discussion of bespoke suits and bespoke shoes. In Fleming’s era well to do London civil servants like he and Bond were patrons of bespoke tailors but my instinct tells me that neither would have been regular patrons of bespoke shoemakers. The Lobb Lopez (likely not around in that era) is a beautiful RTW black Mocassin loafer and comes very close to how I’d picture book Bond dressing his feet.

If we’re talking of teleporting Bond to the present day those Lopez still wouldn’t look too far out of place. Unfortunately a navy suit with black tie would be eye catching in all but the most conservative business dress working environments - not a good attribute for a secret agent - so it will be interesting to see how they clothe our hero in the next round of films.

It was getting increasingly difficult to come up with a scenario in the films for Bond to get into his signature tuxedo. Before long it will be difficult to clothe him in anything above a hoody, sweatpants and crocs if he’s to fit in with any urban scenery.

The Literary Bond, like Fleming, definitely seemed to be a bespoke shoes patron in addition to a bespoke tailoring patron (the latter is explicitly confirmed in the text of the books). As mentioned in my previous post, Fleming specified the bespoke detail of throwing knives hidden in the heels of Bond's shoes. As a result, contemporaries like Kingsley Amis suggested that Bond used Nikolaus Tuczek as his bespoke shoemaker since Tuczek was famous for square toed shoes and was next door to a bladesmith. If other English authors at the time assumed bespoke shoes, I think they would know better than us 70 years later.

I agree that the Edward Greens are closer than the Cheaneys as the Cheaneys have an unusual cut to its penny strap and heel counter. I did not include the Lopez since Fleming expressly detailed Bond as wearing square toed shoes. The OP questioned if the GC George matched that description and, with the Cheaneys, I was just providing an example at the same price range that was closer. Apart from toe shape, I agree that the Lopez is a reasonably good match other than its unconventional oval penny slot.

Unfortunately, there is a real dearth of classically styled square toed penny loafers from the RTW English shoe brands right now. The Cheaney Saxon is actually the only one still in production right now. G&G obviously has the Monaco but it is too aggressively styled for Bond.

 

[unknown_user]

It was getting increasingly difficult to come up with a scenario in the films for Bond to get into his signature tuxedo. Before long it will be difficult to clothe him in anything above a hoody, sweatpants and crocs if he’s to fit in with any urban scenery.

I've always thought that the character "Callan" in the brutally down to earth series of the same name was much closer to what a genuine British agent of the 60s and 70s would have worn (though I am aware that much of Bond was written a little earlier).