The Duke of Windsor & 5 Things You Can Learn From Him

The Duke of Windsor & 5 Things We Can Learn From Him

The late Duke of Windsor was known for many things, including the abdication of throne and a country for the woman he loved, the twice divorced American Wallis Warfield Spencer Simpson. His sartorial sense, however, lives on in photographs taken of him from the time he was a teenager through to the end of his life. Short and not particularly handsome, he nevertheless was a popular subject of the paparazzi of the day and at one point the most photographed person in the world. The man knew how to dress and dress well. Interestingly, the Duke of Windsor not only the namesake for the famous Windsor knot, but lessons can be learned from his sartorial instincts. Today, I would like to point out five aspects in dress that should inspire you to incorporate into your outfits.

Odd jacket combination with short, tucked in tie, high waisted trousers, cloth belt and monogrammed shirt

Odd jacket combination with short, tucked in tie, high waisted trousers, cloth belt and monogrammed shirt

1. To Be Your Own Man

The first is to be your own man when it comes to choosing clothing. Be brave and experiment with your own style. When he was the Prince of Wales, the Duke was chastised by his father for wearing brown shoes with a navy suit. Others though started to emulate him and the look took off. He also abolished the frock coat at court and introduced the morning coat, he preferred soft collared shirts for evening wear and opted for grosgrain bow tie and silk facings when other wore plain satin.

A salesman might have told him that a short man should not wear big checks, but he chose these carefully and they looked wonderful on him. He wore ascots with polo shirts and routinely made it onto the best dressed list. There is a wonderful photograph of the Duke and Duchess of Windsor at a memorial service in England years after the abdication crisis. It was a frosty meeting with their family whom the Duke had not seen for many years. However, there they are in their sartorial splendor next to the traditional, yet boring clothing of the rest of the Royal Family. The Duke taught us that there is nothing wrong with standing out. Go now into your closet. If all you see are navy, charcoal and black, get out there and buy a glencheck suit or madras jacket. If your dress shoes are all black and tan, buy some spectators. Learn how to tie a bow tie. Heads turn and compliments only come when you are wearing something daring, something unique that announces your style. A clone is just that, a clone. Be yourself and enjoy being different from everyone else.

DoW in Morning Coat at Funeral 1967

DoW in Morning Coat at Funeral 1967

2. Buy the Classics First

Now that I have told you to be daring, I am now going to tell you to buy the classics first. The classics, by the way, are sometimes difficult to find because big box stores are selling the fashions of the day, not those things that will be worn in five years, much less ten years from today. You may have to go to independent stores, thrift shops, or a bespoke tailor if your budget stretches. Buy the two button charcoal suit from a haberdasher, and the camel hair jacket online and if you are on a budget from a local consignment shop. Harris tweed rarely wears out, so two or three owners may enjoy a jacket. Read the Gentleman’s Gazette and invest some money into men’s fashion books, they are well worth the investment. That way, you’ll learn what a classic is and then obtain it for your wardrobe. The Duke had all the classics and he had them all his life.

The famous multipattern outfit of the Prince of Wales in color

The famous multipattern outfit of the Prince of Wales in color

3. Quality First

This brings us to the third point we have learned from the Duke. He invested in clothing and wore some items for years on end. Buy the very best you can afford, and do not get trapped by salesmen who tell you that certain expensive brands are better made than a smaller label. Most of the time, they are not; do not just go for a “name.” The Duke certainly had some fine items from Savile Row, the Champs-Élysées, and New York but he also had suits made for him by tailors in the back streets of Paris. Examine the items for sale closely. If the retailer cannot explain how they are made, find another retailer. The dinner jacket that you buy today should last you for the rest of your life if you maintain your weight. The Duke owned his from the time he was twenty-one to his death in his early seventies.

In Light Brown & Red with Patch Pockets Spectators Large Checked Tie

In Light Brown & Red with Patch Pockets Spectators Large Checked Tie

Duke and Duchess of Windsor with Dogs September 1941, Miami, Florida, USA

Duke and Duchess of Windsor with Dogs September 1941, Miami, Florida, USA

4. Accessorize Yourself

Select your accessories and have lots of them. I myself have collected from my travels, shopping trips, and thrift shop hunts over one hundred ties. Even if a well made sport coat or a suit are too expensive for you, chances are you afford retail prices for those special socks, ties or bow ties that will transform your outfit. The Duke of Windsor had many cufflinks, often decorated with his initials. Moreover, he almost always wore interesting ties and contrasting socks in unusual patterns and colors.

Personally, I have dozens of pocket squares. I wear antique stickpins in all my ties and have over two hundred cufflinks.  The point is I can wear the same suit twice in the same week, but if I wear it with very different ties, pocket squares, and shirts, nobody is any the wiser. Pay attention to your accessories. Make sure that ties and pocket squares coordinate but do not match. Nice cufflinks can really improve your overall look if the cuffs are the right size. Start collecting accessories and make your collecting a hobby. By the way, the most expensive set of cufflinks ever sold at auction belonged the whom? The Duke of Windsor of course. It was a set made by Cartier London that consisted of double sided cufflinks with e & W brilliant-, single- and carré-cut diamonds. On the back they were inscribed David 23/6/35,  Wallis 19/6/35, both signed Cartier, London; and respectively: Hold Tight and: E 7/5/35. Estimated to bring £70,000 – 90,000, the set sold for stunning £115,250.

5. Take Care of Your Clothes

Finally, learn to take care of your clothes. To be honest, the Duke had a lot of help in this area. The man went into the Great War with his valet beside him. Most of us will never be so lucky to employ a Jeeves or a Mr. Bates. Yet most of us can learn how to store clothes and how to wash a shirt, hang it up to dry and iron it. Your endeavors will add many more months to your investment. Dry cleaners, often break shirt buttons, discolor a white shirt, and shrink collars. Take out the plastic collar stays and throw them away. Get yourself a set of metal stays in different lengths instead. They will last forever and keep your collars looking crisp and orderly. Pick up an inexpensive clothes steamer at the hardware store, so you don’t always have to hang your suits in the steamy bathroom. Do not put your suit in the closet the very day you have worn it. Hang it up on a wooden hanger or valet in your bedroom, steam out the wrinkles, and then return it to the closet the next day. Brush your clothes with a good quality brush, that is handmade so the bristles won’t come out. Spot clean immediately any little mishaps. Only when you cannot put back a crease in your trousers, your jacket is just not be the same again after a cleaning, a spot will not yield for you, or your suit is starting to emit some unpleasant odor should you take it to the cleaners. Polish your shoes regularly. One of the first things anyone notices about you are your shoes. You can own an expensive pair of shoes, but if the heels are worn, and the edges worn down, you might as well be wearing a $14.99 special from Payless. Go through your closet regularly and see what needs to be attended to. Here a local alterations tailor becomes your best friend. He will fix that hem, sew on a button or two, and take your trousers out a notch. He will also reline a jacket that still looks good on the outside and he will put in suspender buttons on your trousers so you can wear really braces. In short, pay daily attention to the condition of your clothes and you will have them for a very long time, even without a designated valet.

What do you find inspiring about the Duke of Windsor’s Clothes? Did you think he wore a Windsor knot or a four-in-hand with thick interlining? Let us know in the comments below.

Keith McKee
Article Name
Keith McKee
Learn how the Edward VIII - later the Duke of Windsor - created a unique style & how you can use his elements to improve your outfits.
30 replies
  1. Reverend Richard de Meath says:

    I agree with everything in this article, particularly in the care of clothes. First impressions count, and it is better to own one really good suit, than half a dozen inferior ones. Good clothes wear well and if they go out of fashion, remember – they will return.
    People remark that I always look smart, a testament to the power of a good wardrobe, clean clothes, polished shoes and the inner confidence that I am the best-dressed man in any circle.

  2. Kory says:

    The man was the master at mixing patterns that anyone else said should not work and made them look amazing together. He new the secret to making stripes, plaids and polka dots work together was having them of different scales.

  3. rico says:

    A good read. I notice that the Duke follows the rules of fashion, while making them his own. This is a man who is no slave to any convention. My admiration and respect for this man and the way he lived his life is renewed. Thank you.

  4. Jonathan says:

    According to Fred Astaire who was a personal friend of Dow the way he got his ties to look like they were tied in what is now called a Windsor knot is to have his tie maker cut them thicker that was normal at the time. I always think that Edward VII gets rather overlooked in place of his grandson where clothes and style is concerned, he probably revolutionised men’s fashions much more than DoW did.

    • Sven Raphael Schneider says:

      He had indeed a thicker interlining rather than a Windsor knot, it was still named after him. Edward VII was indeed even more revolutionary but I think the Duke of Windsor is cited more often because the fashion of 1880 – 1910 is not really seen anymore.

  5. Elliot Nesterman says:

    FWIW, the tartan of the evening suit is MacDonald, Lord of the Isles, hunting.

    The lordship of the isles was forfeited to the Crown by the MacDonalds at the end of the 15th century and since then the title has been accorded to the eldest son of the monarch. Some consider this to be the Prince of Wales’ personal tartan. However, Godfrey, Lord MacDonald, Chief of Clan Donald, is known to wear this tartan as well.

    There is a story that at an event some years ago at which both HRH Prince Charles and Lord MacDonald were in attendance, Charles was overheard to remark, “Say, is that fellow wearing my tartan?”

  6. Ahmed Sajeel says:

    Not a word out of place. Excellent.
    Incidentally only today I remarked on FB to be one’s own person than to pigeonhole oneself as Anglophile or Sprezzatura driven. Neither the Duke nor Gianni Agnelli are remembered for belonging to a stereo-type

  7. Alexandr Cave says:

    As there are a number of different tie knots known as the Windsor, it is a difficult claim to make with any certainty either way that the Duke wore the knot. His valet is on record as stating that the duke tied his tie in the simple four-in-hand, but that the bulk of the ties’ lining gave the knot its distinctive appearance.

    It should be remembered that the fashion for ties at the time was for much thinner, often unlined ties, so the duke’s bulky ties would have seemed unusual anyway.

    What is interesting about the duke’s wardrobe and style, is that we enjoy articles like this and are prepared to follow his example; the fair bulk of his contemporaries were not so accommodating, and the disapproval and mockery can be readily seen in many novels of the period.

  8. RODNEY L. WALKER says:

    I’ve been waiting for an article on the DoW. Cary Grant, Fred Astaire, and the DoW are the icons and standards of fashion that I’ve been following since I was a young man (I’m 59). I have quite a few made to measure suits and sportcoats, as my budget allows, and I always have the Duke and Cary particularly in mind when I select fabrics and patterns. I visualize Fred as I accessorize. I’ve pretty much duplicated some satorial aspect of all these gentlemen with the exception of Fred’s ties as belts.

    I learned years ago to buy the best shoes at the best price (on sale) and take very good care of them. I realized as a young, broke man that a good shoe can make an inexpensive suit look so much better. My rule of thumb is to always buy the best wardrobe item, particularly ties and shoes, on sale regardless of need. If you like it, buy it. Your wardrobe will catch up with them. It is a very good feeling when you are classically or daringly dressed and mention is made or questions are asked of what your wearing. Please find more DoW photos for us to use as fashion inspiration and reference. Thanks!!!

  9. Daniel Gerson says:

    I will acknoledge that he was a trailblazer in some regards, but as it is often the case with them, they venture out too far.

    The plain outfits work, no questions, but the bold choices in patterns, unfavorable cuts and vivid colors don’t work for me. They make him look like a sad clown. This is most apparent when you compare the first two photographs.

    Though apart from the windowcheck and tartan outfits, neither of the others here look to be too out of line with the fashion. Look at the fashion adverts in the TASCHEN series about American ads of the period. They are full of bold colors and patterns.

    But maybe I am just too young to remember the times when everything was plain.

    • Sven Raphael Schneider says:

      Some of his combinations were wild indeed, others rather tasteful. I guess, if you push the boundaries with daring outfits, you’ll inevitably create something that’s over the top and inelegant. On the other hand, some outfits might be really great. If you always just go with the dresscode you won’t be dressed horribly, nor excellently – just average.

  10. Christopher Long says:

    I endorse the wise advice regarding dry-cleaning – it is the enemy of natural fibres.

    As for the DoW, he remains, for me, a troubling character who found himself unfitted to the monarchical role – seemingly an intensely self-preoccupied person, one wonders why he was drawn to Wallis? She offered a way out, perhaps, from a role to which he realised he was temperamentally unsuited.

  11. OldSarge says:

    His choice in clothing was aided by the fact that he was light haired and pale skinned. As an olive-skinned, dark (now iron grey) haired individual, the light browns and chocolates he wore well don’t go on me. However, I definitely agree that a closet full of plain and striped suites is a sure cure for sartorial insomnia. Let there be color and pattern lest one be mistaken for a corporate accountant.

  12. Mark Hollingsworth says:

    One of your best posts – fascinating, well done. I, also, am not a fan of HRH from an historical political perspective, but one cannot ignore the great work he did for men’s style.

    Now, if we could only get all men to follow the advice in this post the world would be a more refined and stylish place!


  13. Hal says:

    Looking at the pictures rather reinforces my general impression of both the individual and his clothing choices.

    He was clearly obsessed by clothing and loved it. He was always interested in a relaxed tailored look. He had huge sums of money to indulge this passion and clearly did so. That said, it seems remarkable how his clothing choices sometimes appear unbecoming, garish or tasteless. Clearly, he was able to choose excellent tailors and clothiers. Given that he could afford – and did get – the very best in clothes, I’m rather left wondering if his better put together wardrobes weren’t just as much an example of having enough money to spend that sooner or later one’s clothes will flatter – their quality will out.

    Certainly, for me, he looks just as often like the vain, preening, rather ordinary man he was, as the dashing and charismatic individual he could be.

  14. Jay Thorington says:

    Splendid article. Especially for the history
    It contains. Two thing stand out it my mind.
    One: Have your own style. Two: Don’t be
    afraid to use thrift shops. Many times I have
    found quality items for which I was looking here. Compliments abound.

  15. Alessandro C. Grigato says:

    I saw,many years ago,a picture of Edward,Duke of Winsdor and Prince of Wales,wearing a Saxony jacket ,a Saxony pair of throusers,a Saxony vest a light chekered shirt and a Tartan tie, ALL IN DIFFERENT PATTERN and perftcly according.Only a Painter can mix that.His tie knot was different according with the line of the tie. Now,talkin’about people i met personally:
    About Gianni Agnelli,he had nothing to do with elegance,his wardrobe was boring and gray like London smog and he had no culture nor back ground to be a Dandy,or even a gentleman.(on dressing).
    Fred Astaire ,with his phisique du role,was elegant even wearing a trash bag.
    E.G.Robinson had a very special good taste and even Christopher Lee,specially wearing tails!!

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