What The Duke Of Windsor Can Teach You About Style

The Duke of Windsor. A title of just one man. A style just as unique.

It was a title created expressly for Prince Edward on March 8, 1937, after a short reign as King Edward VIII, following his abdication from the throne in pursuit of love at the end of 1936.
He wanted to marry an American woman. A divorcée named Wallis Simpson. Like his sense of style, the Duke of Windsor was known for rebelling against the rules of society. Something he is admired for today.

Just as he broke the rules of engagement required of a King, the Duke of Windsor also broke just about every rule in men’s fashion. Notorious for it, he did so with such panache that he was routinely featured as a best-dressed man of style.

duke of windsor style

He wore big and bold checks, a cravat under a polo shirt, large cufflinks and a peacocked pocket square. Although he certainly didn’t care what people thought of his style, he did care a great deal about how he looked. He took care of his apparel and treated it the same as a military man would his uniform. He acquired the finest apparel money could buy and ensured it fit him like a glove before wearing it in public.

So what can we learn from the Duke of Windsor regarding style?

duke of windsor style

Well, first, we can learn to simply be unique. That there is no harm in following your passion whether it be giving up the world for true love, or opting for some sprezzatura in an otherwise classic outfit that others may not understand or condone.

A man of his stature should never wear bold check suits. But he did.

A man of his position should never marry a divorced American. But he did.

duke of windsor style

Confidence is about far more than just what you wear. It’s all about how you wear it. If you think you look great in it, then who is to stop you?

Here are five things you can do like the Duke of Windsor:

1. Reconsider the ascot. Try wearing an ascot under a polo shirt for a unique and dapper casual look. It’s perfect for adding a touch of style to an otherwise every-man ensemble.

2. Don’t be afraid to be bold. While I always recommend a lean and classic wardrobe, adding a bold blazer is never a bad idea. Just remember, it’s far more noticeable, so if you wear it repeatedly, people will take notice. Instead, consider bold accessories such as pocket squares, cufflinks, bow ties, and braces.

duke of windsor style

3. Buy the best you can afford and take care of it. The fact is that a great bespoke suit can be handed down from father to son to grandson if it’s well cared for. A $200 suit from Men’s Wearhouse might last two years with regular wear. It doesn’t mean you have to spend a lot of money to dress well. Consider vintage clothing from eBay and thrift stores or accessories from estate sales. High quality at low prices.

4. Don’t go bold if you can’t manage the basics. Nothing looks worse than a guy who thinks he’s well dressed but looks like a clown to everyone else. I’m a member of a Facebook group for men who enjoy dressing up and most of them are trying yet failing miserably. Snapping selfies wearing polyester Oppo-style suits, matching shirt and tie box sets in bright colors or wearing suits that look like something Larry the Cable Guy’s son would wear to prom. Going bold is a great idea if you can already pull off the basics. Otherwise, it’s a fatal flaw that makes you look less like the Duke of Windsor and more like the court jester.

duke of windsor style

5. Make sure it’s appropriate. The Duke of Windsor often wore daring outfits that got him noticed. However, he also knew when it was time to dress more appropriately. For every picture you find online of him wearing a spirited outfit, you’ll find another of him in a classic charcoal or navy suit, a morning coat or appropriately attired tailcoat. It is vital to know when and where to don such attire.

The fact is there will never be another Duke of Windsor. The title died with the man. But his style remains among us as gentleman around the world imitate his art and ability to be as intrepid a dresser as he was a man.

Thanks, as always, for reading.

Stylishly Yours,

J.A. Shapira
He Spoke Style

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  • Kenny Baird

    he was most likely a nazi, though.