Kate Middleton Outfits That Could've Been Saved By Ditching This One Gaudy Thing

Kate Middleton has a few notable titles: Princess of Wales, devoted mom, loving wife, and style icon. Paparazzi have captured Middleton's style evolution from pre-royal to senior member throughout decades. Her adorable nightclub dresses and early '00s pumps turned into elegant, tailored pieces to match her high status. Though, one constant will likely never escape her closet: a hat. The wife of William, Prince of Wales, has been rocking hats since her St. Andrew's days, but the future queen has tailored her headwear to fit her style as the years go by. 

There are mixed reviews about Middleton's signature accessory — we've covered her best and worst hat moments — but oftentimes, the royal's hats seem to be the one wardrobe staple that holds her back from staying trendy. We get it; part of the princess's beauty routine is staying out of the sun to maintain her flawless visage, but every so often, her outfits are diluted by a gaudy headpiece.

Throwing it all the way back to 2006 — when Catherine, Princess of Wales, was simply Kate Middleton, the girlfriend of Prince William — Laura Parker Bowles and Harry Lopes' wedding was a who's who of the era's royal fashion. Middleton showed up in a perfectly tailored, cream-colored, paisley coat that worked well against the future royal's skin tone. But her feathery fascinator was an adornment that could've been left at home. The wispy feathers looked like Middleton had a plant growing out of her head, though that might've complemented the countryside atmosphere that evening.

In a wild twist, Kate Middleton overlooked every fascinator in her closet and opted for a fedora — yes, a fedora — while stepping out with her husband, William, Prince of Wales, in January 2020. Her Roksanda coat was the perfect post-holiday pick. However, the cobalt blue wool cap, with an added pheasant-feathered band, from the English hattery Hicks & Brown, was a choice that transformed the princess's casual, cold-weather ensemble into a festival-ready uniform (seriously, we're surprised we haven't seen Vanessa Hudgens wearing it at Coachella). The feather band on the hat completely clashed with her coat, and the colors were not complementary of each other. And mixing that blue hue with gray English weather probably also meant that Middleton could be seen all the way in Dublin, Ireland. 

Kate Middleton typically looks incredibly classy when making her annual appearance at the National Service of Remembrance, but in 2022, she opted for an unusual choice of headwear. Her classic pillbox hats and mourning veils are normally featured in Middleton's ensemble, but for whatever reason, the Princess of Wales donned an enormous, wide-brimmed Philip Treacy hat that year. The style choice may have had something to do with it being the first Remembrance Day Service since the late Queen Elizabeth II's death. Even so, it took away from the rest of her outfit, which consisted of a chic, tailored black coat, adorned with the traditional poppy flower brooch that she wears every year.

Kate Middleton's radiance truly shines in the summertime, but the season marks her annual transition to big hats. At the 2023 Royal Ascot, Middleton wore a stunning red Alexander McQueen dress, paired with matching scarlet heels, clutch, and the signature piece of millinery. Her nearly flat, oversized hat was an overstep on the red ensemble, and with the large floral arrangement attached to the headwear, she was hard to miss that day. If the princess had opted for a subtler hat, she would have been able to save the look — though, maybe not. While Middleton looks gorgeous in red, it was the wrong hue for the warm-weather event.

In April 2025, Kate Middleton gave us all quite a throwback when she donned a baker boy hat while visiting Scouts in northwest England. There's no denying that Y2K fashion trends are making a comeback; the classic flat cap used to be seen on celebs from Paris Hilton to Jennifer Lopez, with Kate Middleton being a huge promoter of the headwear back in the day (and today, apparently). While photos from the afternoon prove that Middleton can pull off anything, it doesn't mean she should. The accessory, on top of her knit sweater and wool jacket, made the future queen look like she was about to do some detective work. This isn't "Sherlock Holmes," Kate; leave the earth-toned cap at home. 

A major factor in Kate Middleton's style is her timelessness. Many of her veiled, pillbox hats are reminiscent of Jackie O ... but the fascinators have got to go. Or, at least, tone them down a touch, because with every royal event, the headpieces seemingly grow in size. While attending a May 2025 Garden Party at Buckingham Palace, Middleton's pale yellow fascinator blanketed an entire portion of her head — and the floral details looked like cranial appendages. Combined with William, Prince of Wales' tails and top hat, the couple's party look gave Willy Wonka meets Kentucky Derby.