Prince Harry's Fashion Critiqued by Expert

Critic Derek Guy makes the case that Prince Harry's simple fashion choices reflect his distaste for "the trappings of monarchy."

By Michael Hein

Prince Harry is not a conventional royal in many ways, but a viral fashion critic recently pointed out some of the subtle messaging in his clothing choices. Dere Guy, known for his Twitter presence and his website DieWorkWear.com, took on Prince Harry in a post last month. He shared two photos of the prince with Meghan Markle, speculating that the prince is not too concerned with fashion.

"Prince Harry seemingly has no interest in clothes and (reasonably) dislikes the trappings of monarchy," Guy wrote. "IMO, this shows through his clothing choices (machine-made pick stitching along the lapel reveals this is a mid-tier ready-to-wear jacket). But I wish he would wear a different silhouette. Many of his outfits would be improved by a wider lapel, a higher rise, and better shaping. Compare these two cream linen suits. Heavier fabric, better shaping, and more classic proportions make the one on the right better, IMO."

The accompanying photos showed Prince Harry wearing the same off-white sports coat in two different settings, both alongside Markle who wore something different each time. According to a report by Newsweek, both photos came from Markle and Prince Harry's trip to Nigeria to promote the Invictus Games.

Guy has made a name for himself by combining his in-depth knowledge about fashion and design with his innate sense of humor to post takedowns of many powerful men online – and occasionally, to gas them up. His writing has been featured in outlets including The Washington Post, Esquire and The Nation, while his account has become a staple of X since its acquisition by Elon Musk. He has criticized everyone from politicians and world leaders to celebrities, athletes and random online trolls.

Guy has written about the British royal family in other cases as well. He made headlines back in April for a general critique of King Charles III's fashion sense, citing an inside source who told him that the monarch stopped ordering bespoke suits in the early 2000s. He wrote: "His clothes don't fit that well anymore, and I'm not sure why... I still think that he dressed very well throughout his life, especially when he used Kent & Haste and the older version of Anderson & Sheppard. He exhibited a kind of taste that I'm afraid will be snuffed out as more people from his generation pass away."

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Guy is not the only one to criticize the generational shift within the royals either. Many have said that Prince Harry and Prince William play it too safe with their clothing, keeping it simple when they can and leaning hard on tradition when pageantry is required. It's unclear if the two ordered bespoke suits – hand-stitched clothing cut to their personal measurements – after their father stopped. However, Guy makes the case that Prince Harry is ordering "made-to-measure" suits now that he lives in the U.S.

Guy continues to post clothing-centric commentary on the news of the day over on X. He is also an editor for the website Put This On. So far, there's no indication that Prince Harry has changed his wardrobe based on Guy's input.

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