Published: June 5, 2025
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An offhand comment about how Prince Harry doesn't dress very well seems to have stirred up his fans. So here's a thread on how both Harry and William don't dress well when compared to the older men in their family — and how this represents a broader decline in taste. 🧵

Image in tweet by derek guy

I should say at the outset that I don't care about the drama surrounding the Royal family. I don't care if you're Team Markle or Team Middleton or Team whatever. I am simply talking about clothes. The following is also not meant to be personal jabs; just an honest review.

The first thing to understand is that select members of royal family were incredible dressers. Most notable is Edward VIII, the Duke of Windsor. For a time, whatever he wore, others followed. He popularized cuffed trousers, belts, and a tailoring style known as the "drape cut."

Image in tweet by derek guy
Image in tweet by derek guy

The drape cut is distinguished by its soft shoulders and full chest, which results in excess fabric "draping" near the armhole. After the Duke of Windsor, it was worn by some of the most stylish men of the 20th century, such as Fred Astaire, Gary Cooper, and Noël Coward.

Image in tweet by derek guy
Image in tweet by derek guy

After the Duke, the second most stylish royal is King Charles. When he was young, Charles, like many young men, experimented with the fashion of his day. He often wore single breasted jackets with narrow lapels, as was popular at the time.

Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy

His style didn't really crystalize until the 1980s, when he started going to Anderson & Sheppard, the most famous tailoring house associated with the drape cut. That's when he developed his signature style: double breasted, drape cut suit worn with a tiny four-in-hand.

Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy

The King's father, Prince Philip, was also quite stylish. He got his clothes from John Kent. The tailoring was outstanding, but also very conservative and middle of the road. We will discuss some of these proportions later. But pay attention to the cut of these coats:

Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy

Compared to the men who came before them, neither Harry nor William dress particularly well (which is fine; mediocre dress isn't a character flaw). To be sure, their military and ceremonial clothes are impeccable bc they're still made by bespoke tailors, such as Dege & Skinner.

Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy

But when in more regular clothes, they look like your average office managers. The clothing is pretty unremarkable.

Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy

Let's fist conduct an experiment. Here are two suits of similar color. Which do you think looks better?

Image in tweet by derek guy

If you said the man on the left, then we have the same taste. But why does he look better? It's because the proportions are more classic: a jacket that bifurcates him halfway from that collar to the floor, a slightly higher rise trouser, a lapel that ends midway to his shoulder

Image in tweet by derek guy
Image in tweet by derek guy

When you look at Harry's suits, it's very clear they sit downstream of early 2000s trends. The narrow lapel + short jacket + low rise pants here suggest this may be J. Crew Ludlow. Which is fine, but not in the same class of tailoring as his ceremonial or military garb.

Image in tweet by derek guy
Image in tweet by derek guy

He also combines things in unpleasing ways. A grey suit jacket should never be worn without its matching pants. If you want to wear the jacket on its own, then it has to convincingly pass as a sport coat. You need a textured material such as Donegal to pull this off.

Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy

IMO, if you think this looks good, it's only because the person underneath is famous Prince. Short, tight jackets with low rise trousers, as well as suit jackets worn on their own, are the plague of modern men's dress.

Image in tweet by derek guy
Image in tweet by derek guy

Let's do another experiment. Here are two green overcoats. Which looks better?

Image in tweet by derek guy
Image in tweet by derek guy

If you said the left, then we again have the same taste. IMO, the left overcoat has more verve, as the longer length swishes around the person's knees when they walk. Shorter coats — known as car coats — may be practical if you drive, but they lack drama. Charles knows this.

Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy

Some people noted that this outfit on the right is great because it's from Dior. IMO, you are blinded by the fact that the wearer is famous and handsome, and the label is expensive and "luxurious." But which outfit looks better to you?

Image in tweet by derek guy
Image in tweet by derek guy

IMO, the left looks better because there's more shape through the chest. It also has a good lapel roll, a sign of quality tailoring. See the bouncy chest below and how the lapel almost blooms out of this coat's buttoning point. It's three dimensional, not flat.

Some of William's jackets are better, but on balance, his dress is similarly uninspiring. His penchant for slim navy chinos means that the thin cotton fabric often clings to his legs like saran wrap trying to cover a cucumber.

Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy
Image in tweet by derek guy

If he just went wider with the trousers, and got them from a bespoke tailor, rather than a brand, then they could fit more like the trousers on the right (made by Steed in Cumbria). See how those pants hang cleanly—not a ripple or a pull.

Image in tweet by derek guy
Image in tweet by derek guy

His color combinations are similarly bad. The grey double-breasted sport coat worn with navy pants and white sneakers lacks harmony. It's much easier to wear a darker jacket with lighter colored pants. So simply switch the colors around: navy jacket, grey pants, traditional shoes

Image in tweet by derek guy
Image in tweet by derek guy

I recently had dinner with a Savile Row tailor who told me that Harry and William once shared the same suit, which they had adjusted for various occasions. Neither have much patience for fittings. In his autobiography, Elton John once reflected on Princess Diana and her son Harry

Image in tweet by derek guy

I personally think this is fine. Not everyone has to be interested in clothes, and as a matter of sociological reality, William and Harry come from a different generation than Edward VIII, King Charles, and Prince Phillip. They are products of their generation, like all of us.

Image in tweet by derek guy

But I do think there was something special about that older way of dressing, especially when it was made by tailors, not designers. And for men who like that sort of style, you can still wear it today without it looking like historical cosplay.

Image in tweet by derek guy
Image in tweet by derek guy

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