The Duke of Windsor’s Influence on James Bond’s Clothes


The Duke of Windsor is famous for the fashion innovations he made in the 1920s and 1930s during his years as the Prince of Wales, most of which still carry on strongly today some 90 years later. No member of British royalty has had such an impact on menswear since. James Bond’s creator Ian Fleming, however, was no fan of the Duke of Windsor, more for who he was than his style.

Many people in the United Kingdom were not fond of this man—once called King Edward VIII—for a number of reasons. He was not seen as loyal to Britain, for he chose to irresponsibly abdicate the throne to instead marry the twice-divorced Wallis Simpson. Even worse, the Duke of Windsor visited Nazi Germany in 1937, leading people to believe during World War II that his sympathies were with the Nazis rather than the Allies. Edward lived his life after King exiled in France, being physically as well as spiritually removed from Britain. It’s no surprise that someone who fought for Britain during World War II would dislike the Duke of Windsor.

Ian Fleming hinted at his dislike for the Duke of Windsor with the now-famous line in From Russia with Love about the Windsor knot:

Bond mistrusted anyone who tied his tie with a Windsor knot. It showed too much vanity. It was often the mark of a cad. Bond decided to forget his prejudice.

This prejudice against men who wear the Windsor knot stems from a mistrust of for whom the Windsor knot is named. Edward actually did not wear a Windsor knot but instead wore ties with thick interlinings that could make a large knot tied in the four-in-hand manner. Still, people have since associated the knot with Edward. The Windsor knot may possibly have been named after the Duke of Windsor because it created a larger knot like the ones he preferred. Edward wrote of the knot in his 1960 book, A Family Album: “The so-called ‘Windsor knot,’ was I believe regulation wear for G.I.s during the war, when American college boys adopted it too. But in fact I was in no way responsible for this. The knot to which the Americans gave my name was a double knot in a narrow tie- a “Slim Jim” as it is sometimes called.” Nevertheless, he is still often mistakenly credited for inventing it and wearing it.

Sean Connery wearing a Windsor knot in Dr. No

Edward’s tailor, Frederick Scholte, developed the relaxed and full ‘English drape cut’, which the Savile Row tailoring firm Anderson & Sheppard adopted. Fleming referenced Anderson & Sheppard in his description of Count Lippe’s clothes in Thunderball:

He was an athletic-looking six foot, dressed in the sort of casually well-cut beige herring-bone tweed that suggests Anderson and Sheppard. He wore a white silk shirt and a dark red polka-dot tie, and the soft dark brown V-necked sweater looked like vicuna. Bond summed him up as a good-looking bastard who got all the women he wanted and probably lived on them—and lived well…

In mentioning Anderson & Sheppard and thus the drape cut, Fleming is loosely making a comparison of the SPECTRE operative Count Lippe to the Duke of Windsor.

Edward is well known for his contributions to fashion during his time as Prince of Wales, whether those contributions are his own inventions or just garments he popularised. Even Ian Fleming and James Bond of the films embraced some of Edward’s fashion innovations.

Ian Fleming did not specify enough details of the literary James Bond’s clothes to be able to compare his clothes to Edward’s. Generally, the literary Bond did not share much sartorially with Edward. One thing we know that Fleming shared in common with Edward was a fondness for wearing belts with his suits. In the 1950s, braces were suits were still very common, but neither Ian Fleming nor Edward cared for braces. Edward wrote in A Family Album:

I never had a pair of trousers made by Scholte. I disliked his cut of them; they were made, as English trousers usually are, to be worn with braces high above the waist. So, preferring as I did to wear a belt rather than braces with trousers, in the American style, I invariably had them made by another tailor.

Fleming copied this style of trousers, though they had become more mainstream in Britain by this time.

Dr. No Dinner Suit
Sean Connery wearing a midnight blue dinner suit in Dr. No

More of Edward’s influence on James Bond can be seen in the films. Edward made many innovations in black tie during the 1920s and 1930s that James Bond adopted. Midnight blue for evening wear was his invention. This started with white tie but soon made its way to black tie. The notes for Edward’s midnight blue evening dress at New York City’s Metropolitan Museum of Art describe part of the reason for Edward’s choice of midnight blue over pure black:

In the 1920s, the Duke of Windsor, then Prince of Wales, introduced the midnight blue evening suit as an alternative to the conventional black evening suit. He was motivated by a desire not only to soften men’s formal wear, but also to augment his sartorial standing in the popular press. As he explained in A Family Album, “I was in fact ‘produced’ as a leader of fashion, with the clothiers as my showmen and the world as my audience. The middle-man in this process was the photographer, employed not only by the Press but by the trade, whose task it was to photograph me on every possible occasion, public or private, with an especial eye for what I happened to be wearing.” The Prince of Wales understood the photogenic possibilities of midnight blue in black and white. Unlike black, midnight blue allowed for the recognition of such subtle tailoring details as lapels, buttons, and pockets.

James Bond favoured this colour for his dinner suits, which can be seen in the first film Dr. No as well as in many others since. Apart from the reasons of photography, the colour is famously said to look “blacker than black” under artificial light. It does, however, look blue in sunlight, which is still a concern some people have when wearing midnight blue during evening events in the summer time when the sun is out past 6 pm. But in black-and-white photography it will always look black while still being able to show more definition.

Bond also favoured the kind of soft dress shirt that Edward invented, according to Alan Flusser in Clothes and the Man, in the 1930s, which made the stiff shirt obsolete for black tie long before James Bond appeared on screen in 1962. This shirt has a soft turn-down collar instead of a stiff wing collar, soft double cuffs instead of stiff single cuffs, and a soft pleated front instead of a stiff boiled front.

According to Gentleman’s Gazette, grosgrain silk facings instead of satin silk for evening wear was another of Edward’s innovations. Costume designer Lindy Hemming was a fan of grosgrain silk and dressed James Bond in Brioni dinner jackets with grosgrain silk facings in Tomorrow Never Dies, The World Is Not Enough, Die Another Day and Casino Royale. Daniel Craig’s ivory Tom Ford dinner jacket in Spectre also has grosgrain facings, though facings on an ivory dinner jacket were not done during the time of the Duke of Windsor.

Pierce Brosnan’s dinner suit in Tomorrow Never Dies has midnight blue grosgrain lapels and a large bow tie reminiscent of what the Duke of Windsor wore

Sean Connery’s, George Lazenby’s, Roger Moore’s and Daniel Craig’s Bonds all wear suit trousers that have various self-supporting systems. Edward was actually one of the first to wear trousers with a self-supporting system. New York City’s Metropolitan Museum of Art has one of Edward’s morning suits with such a pair of trousers, which they described:

While he had his jackets made by Frederick Scholte, he had his trousers tailored by Forster & Son … To avoid the necessity of wearing either a belt or braces to support his morning trousers, Forster devised an internal elasticized girdle, which fastened at the center front with a series of adjustable hooks and bars. To prevent gaping, two vertically positioned trouser hooks were set on either side and hooked over the tight fitting girdle.

Though Edward’s grandfather Edward VII was the first to wear a suit in a Glen Urquhart check suit, Edward VIII is responsible for the glen check suit’s modern popularity from when he wore them often as the Prince of Wales. James Bond is a big fan of the glen check suit, and Sean Connery wears five over the course of his six Bond films. George Lazenby, Pierce Brosnan and Daniel Craig also wear glen check suits in their Bond films.

Daniel Craig in a Prince of Wales check suit and tab-collar shirt in Skyfall

Alan Flusser also attributes the tab collar to Edward when he was the Prince of Wales. Though the tab collar is generally too fussy for James Bond and has become more of an American style since its origins in Britain almost a century ago, costume designer Jany Temime established it as a Bond style when she dressed Daniel Craig in them throughout 2012’s Skyfall.

James Bond and Edward both shared a hatter, James Lock & Co. Lock takes credit for providing Sean Connery’s brown trilby the first Bond film Dr. No.

Sean Connery with his lock trilby in Dr. No

Despite James Bond’s creator not being a fan of Edward, the character is unable to avoid many of the fashions started and popularised by Edward. Thankfully, James Bond did not copy all of Edward’s fashion innovations. James Bond has yet to wear brown suede shoes with city suits, saving them for casual use and country sports coats. James Bond has also never worn the two styles of suits that Edward is known for wearing. He never wears a button two show two double-breasted suit with a lapel that rolls down to the bottom button, and he never wears a button two suit with a high stance that is cut for both buttons to fasten. And none of James Bond’s suits, even the fullest-cut of Connery’s, had the level of drape that the Duke of Windsor encouraged his tailor to give his suits.


  1. Thanks Matt!

    Edward Windsor was indeed a rather dubious figure – in UK he is still referred to as the “Traitor King” – his sympathies towards fascism are well remembered down to the present day. Furthermore it has always been known that he never belonged to the brightest minds on earth – and that’s putting it mildly. I must say that it makes me feel a bit uneasy everytime he is being praised for his sartorial “achievements” without taking into account his many shortcomings. I very much appreciate the way you have tackled that in your article.

    As to his style: I was never crazy about his beloved Scholte drape cut and IMO the Prince’s love of pattern sometimes yielded to a rather excessive (over)use of them. Suede shoes worn with lounge suits are nowadays a classic – especially in Italy but this as well as most of Windsor’s other “inventions” would indeed not work for Bond since the first’s overall style was rather garish and therefore is contradictory to the latter’s sober way of dressing.


  2. Who knew Bond’s and Windsor’s clothes shared so many similarities?
    The Windsor knot is excessive to my eyes, anything other than a four in hand for a necktie is dumb in my eyes.
    Excellent article, Matt. Are you going to do a comparison of Bond’s and Leiter’s clothes in Live and Let Die?

  3. Edward as Prince of Wales and King Edward VIII,was very popular and beloved from British peoples.
    This changed little after the abdication.
    The nazi thing is a rather recent affair; jumped out in 70s, before was not a problem.
    I think that the Duke not understand anything of politics,and many in UK in those years wanted avoid a new war; great part of establishment believed also that the real danger was the communist Russia not nazi German.
    Was a mistake for sure,a mistake which involved many, but before the war was a different era.

    Anyway the literary James Bond is a more racist and right wing type than the poor Duke was.

    • The Duke of Windsor’s trip to Nazi Germany was reported at the time, and that surely must have left a bad taste in the mouths of many and likely contributed to Fleming’s dislike of the man. I’ve understood that the Duke of Windsor was not like by many people in the UK during his lifetime, but I’ve gathered that he has always been more popular outside of the UK (with the same going for his style of British tailoring).

  4. Sincerly i not remember any reference to nazi sympathy During the long life of the Duke (he die in 1972).
    Was only in late 70s and 80s the this thing come out.
    Back then the Duke was at most was considered frivolous or irresponsable,not as a crypto nazist.
    I think that he was a completely unprepared and clumsy in politics.

    • I think that much of the Nazi connections didn’t come out until later, but I think it upset some people that he went to visit Nazi Germany. “Frivolous or irresponsible” may have been enough to make plenty of people dislike him too.

  5. A very balanced portrait of the man and his style. I don’t know if his menswear contributions would be as widely loved and emulated had they happened after his abdication and later Nazi sympathies. Regardless, we have him to thank for relaxing black tie and other menswear dress standards a bit. I believe he may also have popularized trouser pleats and turn ups, but am not 100% sure on that.

    Sadly, the series The Crown got much of his style wrong. One of the most egregious is that he’s seen wearing a stiff wing collar with black tie. Winston Churchill, from what I can gather, appears to have worn both a stiff imperial collar and a soft turndown collar with black tie. So it makes a little more sense for him to wear the imperial in the same episode. Edward, on the other hand, innovated the soft turndown collar evening shirt and I’ve never seen him wearing anything but that in pictures. Sloppy work along with them giving him a narrow Windsor knotted tie instead of a wide, thickly lined, four-in-hand knotted tie.

  6. Matt I was under the impression that it was his grandfather Edward VII when HE was Prince of Wales for whom PoW patterns, evolviing from Glenurquart checks, were named.

  7. Matt, i agree with you.
    Frivolous and irresponsible ( and i add also silly) may have been enough to make plenty of people dislike him .
    But be a nazi traitor is a different thing.

    The visit to Germany was in 1937:

    “The Duke was formally invited to visit Germany, and he was very keen for the visit to go ahead, notwithstanding the fact that the British government were not in favour of the trip at all. They preferred the Duke and his wife to maintain a low profile, but the Duke wanted to try and foster peace between Germany and Britain. He was not alone in that wish and some senior members of the British parliament were also keen to pursue any diplomatic measures available to try and ensure peace was maintained. The British government was almost bankrupt after World War I and the Great Depression, so peace made infinite sense to many in the Government.Peace, and his anticipated role as a negotiator between their two countries, was not the only reason that the Duke was very keen for the visit to go ahead. He also wanted Wallis to experience a State Visit. Naturally, he had family in Germany and he and Wallis were very well received by the German aristocracy. Wallis was treated like a princess and with the distinction that he believed she was due”.

    Still in 1938 Prime Minister Neville Chamberlain ,in Munich,made a desperate attempt for keep the peace.
    A deal was reached on 29 September with Adolf Hitler.
    On 30 September, upon his return to Britain, Chamberlain delivered his infamous “peace for our time” speech to crowds in London.
    Unfortunately for that gentleman,Hitler was a insane criminal,chief of a criminal regime.
    Every agreement with him was impossible.
    Chamberlain deceive themselves,so the Duke of Windsor.

  8. If I may chime in, using a little bit of psychological analysis:-

    Edward was born, under the eyes of the British people, a lucky person – the continuation of the royal blood line – and was assumed to be a happy man. But through the documentations, memoirs, and his point of view, I sincerely doubt it. The prince was simply a person – a child at that – and what people assumed is not what the reality really is. It turns out that his father, the King, was a cold, harsh person, who spared no love for Edward, even when he was a child. Worse yet, when I read the memoir of the Prince, I actually felt rather bad that his tutor was allowed to slap him – on the wrist that is – for a crowned prince, the king in waiting, he actually had an awful childhood. The King and Queen were dedicated to their people, their country, but in return, none of them – King George or Queen Mary – were ever attentive enough to the young Edward.

    From a psychological perspective, honestly, the downfall of Edward was from since the day he could remember.

    For what it’s worth, people kept remembered the rebellious attitude of Edward when he went to Nazi Germany, whilst they were willing to forget the fact that the crowned prince of the British Empire went to the First World War, right to the front lines, to be with the troops. It is rather unfair, for we the people were so ignorant, and we easily forfeit what one did that was good with what we saw as bad – not that I approved of his relationships with Nazi Germany.

    Now, the relationship between the late Duke and Bond’s – or Fleming’s – preference of tailoring.

    We know the Prince loved drape. Scholte cut him the first variants of drape cut, and he made famous of it. From that drape cut, comes soft tailoring, or implementation of drape into the many different cuts on Savile Row. Let’s keep it most relevant here – Anthony Sinclair incorporated drape chest into his otherwise very clean and slick Conduit Cut, and the drape is even more apparent and full in the cuts of Cyril Castle. The concept of soft tailoring was also prominent in almost all of James Bond’s tailoring. Ian Flemming, though not wearing drape exclusively, wore soft garments as well. So, like it or not, the implementations of drape is everywhere, and let’s be honest here – I know of Scholte, but when it comes to the image of drape, the image of the Duke of Windsor comes first and foremost. Let’s be real here, we don’t even have a picture of Scholte himself, for crying out loud! So, the influence of the Duke’s tailoring is endless, especially when he was photographed so much. When it comes to tailoring, undoubtedly, image and vision comes before anything else.

    Conclusively, I tend to think that there is an inner conflict when it comes to the influence of the Duke on Bond and, to an extent, Flemming himself. Evidently, the tie knot, the choice of color(s) and pattern(s), and eventually, the image and the cut of the suit.

    That would be all for now, I supposed.

  9. Great (and fair) post.

    Yes, he ws a bit of an upper class dimwit. And yes, he (like many UK upper class of the time) liked Hitler’s ironfisted approach to social issues.

    On a lighter note: if you are interested in the type of luxury transport the Duke used, Google “Duke Of Windsor car”.

    You’ll find links to “The Duchess”, the highly customised (and very expensive) Cadillac that Eddie used to get about in.

    And you thought his clothing was extravagant…

  10. Can anyone explain to me the concept / reason behind a pic I once saw showing how the DoW had his strides made with built in boxer shorts? (This is hardly a detail that would be adapted by the unfussy and utilitarian Fleming / literary Bond.

    • Mastroianni’s suit: Sublime!
      Of course he was a very stylish man anyway and probably will remain one of THE style icons forever. Molto elegante! 🙂

  11. What type of suit or feature allows one to button the bottom button? I know this was something JFK did as well and I read that he had his suits specifically made with that detail in mind. So what makes a suit special enough to button both buttons?

    • I’ve seen it called the “paddock” cut. Compared to a normal button two, the buttons are placed higher, and both buttons are aligned to fasten, with the cutaway starting below the bottom button. JFK had some suits cut like this, but he also wears some ordinary button two suits that pull at the bottom button when he fastens it.

  12. The DoW wore show six button two DBs but would allow the lapel to roll lower and button only the bottom button. This may have given rise to the show six button one DBs. Some DBs are cut in such a way that like the DoW you can choose to button top, bottom or both but if the cut is not right it will pull.
    There is a rare photo or two of JFK wearing paddock cut jackets kicking around but mostly he wore traditionally cut 2B jackets, but fastened both buttons to cover the back brace that he often wore underneath.

    • The Duke of Windsor’s double-breasted jackets were always button two show two, for four buttons overall. I don’t recall ever seeing him in a jacket with six buttons. I’ve seen his brother, the Duke of Kent, with six buttons, but he also typically wore the button two show two closed at only the bottom, and it’s the corruption of this style that gets his name. The bottom button of a double-breasted jacket should never pull when fastened unless it isn’t fitted properly. Whether a button two double-breasted jacket can be fastened only at the bottom isn’t so much about the cut but rather the construction. A stiff construction will not allow this.


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