How the Duke of Windsor became a style icon

rince Edward, Duke of Windsor, formerly King Edward VIII and Wallis Simpson

It’s fair to say that the Duke of Windsor was not a great King, with his reign being only 326 days and the shortest in the history of the British Monarchy. His abdication in 1936 was due to his proposal to marry twice divorced Wallis Simpson, an American socialite at the time. Such a marriage would have conflicted with the Monarch’s role as head of the Church of England, not to mention the staunch opposition from the government of the day, lead by Stanley Baldwin.

Colour photograph of Edward, Duke of Windsor wearing a white suit and Wallis

Whilst politics and his role as King were not his strongest attributes, one thing the Duke of Windsor was world renowned for was his impeccable sense of style, not only by his choice in clothes, but how he matched them and how he wore them with pride.

For the time, he was extremely modern in his approach to clothes, having them made for comfort, which he described as “dress soft”. One element of fashion that he was particularly keen on was pattern and this is evident in a large amount of his outfits. His passion for pattern was particularly interesting due to his height of just 5’5”, however he was clever in his cuts and his jacket waists were abnormally high to elongate his legs, which in turn meant he could carry off bold prints.

Duke of Windsor and Wallis jumping

His fashion was remarkably similar to his life and just in the way he showed disregard for the establishment, he also showed disregard for the fashion rules of the day. One such example is that he insisted on having cuffs on his trousers, which apparently enraged his father, George V.

As well as his love of pattern, he also showed a fondness for texture in his dressing and paired them in ways that were revolutionary for the time, such as patterned shirts with striped ties.

Despite him living in France for most his life he was a strong supporter of British clothing manufacturing choosing Scottish tweeds and Fair Isle sweaters over that of Europe’s more modern fabrics.

During his life he used the same tailor, Scholte of Savile Row, who tailored his outfits to his extravagant tastes and lifestyle, such having his left pocket on his trousers cut wider to accommodate his cigarette case or fitting his trousers with an elastic waist as he disliked suspenders. He also preferred zips instead buttons for his flies, which was a relatively modern difference for the time.

Duke of Windsor 1936 with Wallis Simpson, wearing a polo shirt

In 1960 an inventory of his wardrobe was taken that recorded he owned an impressive 15 evening suits, 55 lounge suits and three formal suits, along with small 100 pairs of shoes. He was clearly a fashion addict, who is as admired by the fashion world today, as he was then.

Despite his obvious love of clothing, he was only once quoted talking about his style saying, “I was in fact produced as a leader of fashion, with the clothiers as my showmen and the world as my audience.”

Get the look:

The double-breasted blazer

Famously worn by the late Duke of Windsor, the double-breasted blazer is just as appealing decades ago as it is today. The best part is, the jacket’s versatile guises means it can be worn at almost any time of the year – with fabrics like linen suited for the warmer months.

Double-breasted wool blazer in camel, £325,, double-breasted wool, silk and linen blazer in navy, £325,

The bold tie

A true gentleman can pull-off a bold tie effortlessly, and like the Duke of Windsor, sporting a bold-patterned tie with equally bold colours will set you apart from the rest. Worn with a plain shirt, a bold tie can elevate a double-breasted blazer, too.

Button-cuff shirt, £90, and woven silk tie, £125,

Thomas Pink Frederick plain shirt and Turnbull & Asser tie

The checkered 3-piece suit

The late Duke of Windsor was in high favour for the checkered suit, and a lightweight, two-buttoned design is the quintessential update that bolsters modern, gentlemanly style.

Suit jacket, £275,, matching waistcoat, £115, and matching trousers, £125,

Reiss Bullard checkered navy suit

The dinner suit

Every gentleman’s essential, not only for the Duke of Windsor, the dinner suit is a worthy investment that will never go out of style. Remember to include a careful selection of accessories like a pocket square and lapel pin, too.

Dinner suit, £299,, Derby shoes, £175,, silk pocket square, £25,, Charvet polka-dot silk-faille lapel pin, £95,

Further Reading