Kate Middleton's Best And Worst Winter Looks Have Heads Turning

Kate Middleton is known around the world for her impeccable style. She's a constant fixture on the pages of fashion magazines the world over, and pretty much anything and everything she wears sells out instantly as soon as she's photographed in it. And that's just as true when it comes to her winter style as it does her looks during other seasons. As Daena Borrowman, jewellerybox's marketing manager, explained to Express, "The Princess of Wales' Christmas day church service outfit has been a much anticipated annual festive highlight by fashion editors and royal fans alike." 

There's no doubting she's rocked some absolutely stunning outfits to beat the chill year after year, providing us with the ultimate look book for cold weather. But, well, as much as we hate to say it, not all of the Princess of Wales' more covered up looks have been quite so stylish. And, when the world is watching, no matter if you're at your fashion best or worst, there's been a whole lot to be said about Middleton's winter style.

In 2015, the then Duke and Duchess of Cambridge arrived in Wellington, New Zealand, with their son, Prince Louis — but Kate Middleton's red coat and hat combo just didn't quite work for her. Though the double-breasted fit was no doubt a good attempt at channeling a vintage look, it unfortunately wasn't practical for such a windy day on the opposite side of the world. All while holding a very young Prince George in one arm, Middleton was photographed trying to keep her coat from flying open to expose her thigh and hat from blowing away

It's rare for Kate Middleton to have a fashion misstep, it's true, but we have to say, this blue velvet dress she wore to a reception in Sweden in January 2018 just wasn't one of her memorable moments. Velvet clothing is notorious for adding bulk to the body and, although Middleton can certainly pull it off, it gave her look an unusually matronly quality rather than a chic one. That, coupled with trumpet sleeves and thick trim of velvet around the bottom made the dress reminiscent of a table cloth. The random triangular sliver of blue velvet on her chest also seemed out of place.

To make matters worse, she paired the already drab look with closed toe black heels which had an ankle strap that cut off her long legs instead and made them look short. The royal was pregnant at the time though, so we can certainly let her off for this rare misstep.

Clearly, Kate Middleton's 2018 trip to Sweden wasn't one of her best dressed royal engagement. That same month, she also wore a floor-length satin dark mustard gown decked out in an all-over floral pattern. If that wasn't loud enough, the floor-length gown had extra material gathered below the knee that looked similar to a mermaid dress. We understand it was winter, but this look was just too covered-up for the royal. Not to mention, the gown itself was deviation from her usual color palette — and just didn't pay off. "Can't believe that #KateMiddleton #DuchessofCambridge chose this dress! Looks like curtains!" one person even wrote on Twitter/X. "She normally gets it so right[.] Not tonight."

Kate Middleton is known for her kind heart and her dedication to various important causes, but she caused quite a stir in 2016 when she wore what appeared to be fur-lined gloves on a ski trip. According to E! News, the gloves were by Restelli Guanti and may have been lined with possum fur. Of course, that didn't impress PETA, and the non-profit slammed the then-Duchess of Cambridge's fashion choices in a statement. "If the gloves are indeed made of real fur, we'll be contacting Kate, who we imagine is unaware that possums killed for their fur are often caught in bone-crushing steel-jaw traps," Mimi Bekhechi, the director of PETA U.K., said. "Since so many humane, warm and fashionable fabrics are readily available, there's no need to wear fur ­ possum or otherwise." Yeah, not a great look from the royal.

Though Kate Middleton usually knows exactly how to dress for any occasion, her 2019 Christmas Day outfit was one that even she has admitted to regretting. Stepping out for a church service with her family, Middleton wore a thick, long gray coat with what appeared to contain a faux fur trim along the neckline and cuffs. She sported it with a forest green fascinator and a pair of matching pumps and a clutch. Although she looked warm, it seemed unusually drab and gloomy for a holiday look. 

But she wasn't afraid to tell royal fans that she'd made a mistake with it. Fan Karen Anvil told Metro UK she spoke to Middleton outside the church service, who told her, "I really shouldn't have worn this." As for why? She was just too hot in the stuffy look.

We must admit, we wanted to love this look. The design is elegant and perfect for a royal. We also love the way it drapes over her stomach, which was perfect for Kate Middleton as she was pregnant at the time. But this gown she wore in early February 2018 during a trip to Oslo just isn't one of her best winter looks. And it's mainly because of the color. The nude shade really washes Middleton out, while the sheer fabric over her arms just buries this stunning royal. Seeing as Middleton has cooler undertones, she tends to suit stronger, more vibrant shades, such as jewel tones. And this pale shade unfortunately didn't work compared to some of her best looks.

Back in February 2014, Kate Middleton wore a basic brown coat over a black turtleneck and tights while out in Liverpool. Although the look was relatively chic and inoffensive, it left us wanting more from the fashion icon we know this royal to be. Without any accessories, like a scarf or hat, the earth-toned neutral look was pretty underwhelming.

One of the hardest things to do when it comes to winter fashion is accessorize. But Kate Middleton made that look easy in 2020 during a royal appearance in Cardiff, Wales. The popular royal wore a long red duster with a checked red scarf to keep her warm in the winter cold, and taught us all a lesson about how a single addition can make the difference. "Scarves can often make an outfit look unkempt or mismatched, something to be whipped off the moment we get inside, however, the Princess of Wales shows us that scarves can be stylish," head stylist at SilkFred, Megan Watkins, told Hello! "Kate always matches her scarf to her outerwear," she pointed out.

When Kate Middleton stepped out in a monochromatic winter white ensemble in December 2023, the world took notice. So much notice in fact that WWD reported fashion brand Karen Millen found that online searches for long white coats rose 1,331% in just one week, with a 205% search increase just in the U.S. alone. So, yeah, it's safe to say this look was a total hit. Middleton wore her white coat to a carol service in London, proving it's totally not a fashion faux pas to wear white after Labor Day. The fact that she coordinated it with a white top, tailored pants, and nude pumps only made it seem even more luxurious. Because all-white winter looks can be oh so chic.

Kate Middleton proved that sometimes all you need is a good statement outerwear to do the talking when she stepped out in Bradford, UK, in 2020 wearing a deep, forest green long coat. One of the reasons the look worked so well was because she stuck to her tried-and-true silhouette. "Kate loves her outerwear, but if you look closely, there's a trend among her choices — tailoring," Megan Watkins explained to Hello! "Opting for a structured coat with padded shoulders that is long-line and oversized provides warmth whilst giving you shape is a key look of the Princess'."

It's not all about coats when it comes to Kate Middleton's best winter style looks. In December 2023, she hosted the TV airing of a Christmas carol service and wore the most stunning and elegant white sparkly boucle jacket in an ad for the segment. The Princess of Wales' outerwear caught the light in the most stunning and delicate way as she stood in front of a Christmas tree, with its white sequins shimmering in the camera. The stunning piece was also adorned with white pearls, making it perfect for not only for the royal, but also for the regal event.

We just adore Kate Middleton in a fitting royal blue, and her 2023 Christmas Day outfit proved exactly why. The color was perfect for her complexion and highlighted her glowing skin, which was necessary on a cold, winter day. Middleton was smart with accessory choices, pairing with pieces that let the coat shine. The long dark blue suede boots were both stylish and practical, while her matching, dark turtleneck made for the ideal base layer. Then there's the matching clutch bag and fascinator, which gave the sophisticated look an extra edge.

Though Kate Middleton's plaid coat dress may not be her most exciting winter look, what it does do is prove she usually knows how to dress for her body. The princess kept the colors of her outfit limited to a muted blue palette for the season while visiting Scotland, but wore black tights that made her legs look long and lean. The cinched waist on her checked coat highlighted her waist, while the metallic buttons added a royal quality to the look.

Walking through the city streets in the winter, you're likely to see a sea of dark grey, brown, and navy. 
This is one reason why we adore the way Kate Middleton brought a pop of color into a neutral brown duster look she wore during a trip to Boston in December 2022. The flash of orange was an unexpected choice for the royal (which may be why this is one of her best looks) but still works under the chocolate brown coat. The color really saved what could have been a pretty drab and somewhat boring outfit.

Kate Middleton made the shift to wear more pantsuits around 2023, and this red one has to be one of our favorites. The star looked so chic in January of that year wearing the slightly plunging look, made up of a red jacket, matching pants, and a red top. And she once again proved how great she looks in a monochrome outfit. Not only was it striking and bold, yet still chic and sophisticated, but the color was spot on for her. That's because this vibrant red really complements the Princess of Wales' warm skin tone and rich brown locks. Plus, it's a total power move to wear a pantsuit like this, and we adore it.

Along with her penchant for Catherine Walker dresses, Middleton loves a good court shoe, even in the chilly weather. And she does even better when she combines the two into a monochrome look, like the ensemble she wore to a 2021 Christmas carol service. Complete with red velvet pumps and a giant red bow on her collar, the princess looked beyond stunning, and totally appropriate for the festive occasion. Plus, there's no doubting red is totally her color (but then again, what shade isn't?). No wonder Daena Borrowman gushed to Express that the royal "dazzled in yet another monochromatic ensemble" after the photos from the event went public.

In November 2023, Kate Middleton's black military inspired coat, large black hat, and stunning earrings totally stole the show. The Catherine Walker coat dress featured a high collar and zipper with tassels stitched to either side, and three red flowers pinned to her left shoulder. The princess wore her hair in a tight chignon underneath her hat and a pearl brooch on her ear. The look was demure, yet appropriate for the occasion, which honors service people and those who lost their lives in battle. Perhaps Miranda Holder said it best on TikTok, when she told her followers of this sophisticated look, "Despite all this sadness, Kate's immaculate fashion absolutely cut through and did hold its own, and is, by its very nature, totally newsworthy in itself."

We know Middleton is a fan of recycling a look, and that has served her quite well in the winter coat department. For Christmas 2016, Middleton was spotted with her family wearing her famous chestnut brown Hobbs Celeste coat, a piece of outerwear that she's been sporting since 2012.

However, this time, she decided to dress it up in a way that had the fashion experts totally losing it, by going totally bare-legged. But what really made the look standout was her accessory choices. "She repeated her chestnut brown Hobbs Celeste coat with a jaw-dropping red fur scarf, proving that the addition of the right scarf can elevate a basic coat from drab to utterly sensational," Daena Borrowman told Express of the look.

It's not just about outerwear when it comes to Middleton's winter style. In fact, one of her best looks came in the form of an Alexander McQueen evening gown she rocked while walking the BAFTA awards red carpet with her husband, Prince William, in February 2023. Middleton looked like an ethereal goddess as she braved the British cold in the one-shoulder, Grecian inspired dress that cinched at the waist to highlight her stunning figure. Opposite the bare shoulder was a flowy sleeve that swung like a cape. Middleton finished the elegant look with a little extra warmth by wearing contrasting black bicep-high gloves and dangling earrings, which really made this look fashion-forward.

One Kate Middleton's biggest fashion wins has to be in December 2022 when she attended the Earthshot Prize awards in Boston wearing a stunning vibrant green dress. The floor-length off the shoulder dress certainly grabbed attention, while the long sleeves no doubt kept the Princess of Wales warm in the chillier weather. And fans clearly loved it. One person even commented on Twitter/X, "Princess Catherine The Princess of Wales just looks incredible and iconic here when she attended the Earthshot Prize Event."