Outdated Outfits Pippa Middleton Was Caught Wearing

Royals like Catherine, Princess of Wales are seen as some of the most influential fashion icons. Who can forget Kate Middleton's magnificent wedding dress, as well as many other stylish and classic looks she's worn since? Kate's clothing choices are constantly making a stir and selling out designs as fans try to channel the princess' look. But, Kate is not the only Middleton to cause a commotion. Her younger sister, Pippa Middleton, has had her share of memorable fashion moments, including at her own wedding. 

Since becoming connected to the royal family, Pippa has been in the spotlight and has drawn a lot of attention for her fabulous hair and, at times, amazing style. But she's also had some fashion flops, and her aesthetic is often a little behind the times. The British royals typically dress in a more modest and conservative style as opposed to following the latest fast fashion trend. This is something that Pippa has done her best to emulate and, at times, accomplished flawlessly. But, while traditional looks can be beautiful, it's also easy to get wrong and appear out of style. Some of Pippa's fashion choices have unfortunately fallen flat, causing her to look less classic and more aged and outdated.

A wedding is one of those special ocassions where everyone gets to bring out their best styles. Pippa Middleton became particularly well-known for wedding looks after stunning in a white gown as her sister Kate Middleton's maid of honor in 2011. But, her nuptial 'fits have been more hit or miss since then, and unfortunately, this boldly-patterned peplum dress that she wore as a wedding guest was a definitive miss. Although the black and white print of the dress has the potential to look quite chic, the hyper-conservative neckline and sleeves paired with the peplum waist make the whole outfit feel old-fashioned and dated. 

Stylist Charlie Anderson shared her disparaging opinion on this wedding guest look with the Daily Beast. "This black and white wedding outfit is not bad, but it still manages to miss the mark. Is it the matchy-matchy accessories? Or just the lack of a modern, flattering cut that does it?" Anderson questioned. The dress was worn in 2013 when peplum was more stylish, but as Anderson points out, the cut of the dress is still not done in a very modern way. On top of that, her black clutch, heels, and matching black hat make the whole outfit feel stuffy and outdated. 

There are so many fashion rules that they often feel arbitrary, and many style icons are known for breaking them. British royals have even more strict fashion rules than the general public, although the royal family doesn't always follow them. But while they can be restricting, style guidelines can also be useful if you want to avoid your outfit calling negative attention. Pippa Middleton made a fashion faux pas by wearing nude pantyhose. Although it used to be expected for women to wear tights under their dresses, flesh-toned hosiery has become old-fashioned in recent decades. They're more often worn by dancers and elderly women than by people Middleton's age. But she's been seen wearing these tights frequently, and it's caused a lot of criticism. 

Although they may keep legs warm, nude tights make an outfit feel instantly outdated. Whereas a pair of sheer black pantyhose can be sophisticated, many style enthusiasts feel nude pantyhose should simply never be worn. "The only time a woman belongs in tan hosiery is if she's performing Swan Lake! It's next to impossible to find a pair that matches your skin tone well enough to look like your natural legs and summer is high time to flaunt your beautiful bare skin, not cover it up in an uncomfortable pair of stockings," Glamour's Tracey Lomrantz Lester wrote. The nude tights make Middleton's cute, flowy dresses seem frumpy instead of youthful. 

Pippa Middleton is a highly sought-after wedding guest. It seems hardly a weekend goes by without her putting on her Sunday best for a friend's marriage. Unfortunately, many of her guest looks are very out of date, like this peacock blue dress and matching hat. While it's good to see she's not upstaging the bride with anything too racy, it would be nice to see her in something a bit more current. 

The overly matchy-matchy style of the hat, shoes, and clutch follows antiquated fashion rules and instantly makes the ensemble feel stuffy. But Middleton is not to blame for this outdated fashion choice. Looking at any photos from royal weddings, you'll see dozens of women wearing ostentatious hats matched to their dresses. It's a common style that can be done quite well. But the combination of matching blues, old-fashioned lace, and conservative cut makes Middleton's whole look feel tired instead of tasteful. 

She often leans too far into traditional looks to the point of aging herself. Instead of feeling timeless, this style ends up dated and ages Middleton. 

Between details about Meghan Markle's extravagant wedding look and the drama surrounding her tiara, you could have easily missed any mention of Pippa Middleton and the outfit she wore to Prince Harry and Markle's nuptials. But, her guest look did draw some attention and internet buzz, unfortunately not in the way she might have hoped. 

Middleton wore a floral dress with a high neck and a traditional cut, along with a floral hat. It had a distinct color combo: the main portion of the dress was light mint green, and the paneling and florals were dusty pink. While the mint shade was popular in the earlier 2010s, it already felt dated by the 2018 wedding. On top of that, the pairing with pink reminded many of an Arizona Iced Tea packaging. 

Middleton likely wasn't hoping to bring any such comparisons, but users on X, formerly known as Twitter, were quick to point out the similar shades. Many shared side-by-side photos of Middleton in her dress next to the canned drink. One user wrote, "Pippa Middleton sponsored by Arizona," in their X post. Others shared similar jokes; the brand even got in the fun when they shared a photo of Middleton and their tea and wrote, "Pippa got you feelin' thirsty?! Stop by the Great Buy 99 Pop-Up for a free can of the real thing!" (via X).

Pippa Middleton wore this outfit to an event in 2012, but the old-fashioned style of the skirt and blouse makes it look like it could be from decades earlier. Pairing the skirt with a puff-sleeved blouse creates an old-fashioned business casual appearance for the entire look. High-waisted skirts are a classic style that is often very flattering. However, this took things a bit far. Instead of coming up to Middleton's natural waist and cinching her, as most high-waisted bottoms would, the pencil skirt shoots straight past her waistline and sits just below her bust. The shortened chest and overly high waist look uptight and out of trend. 

Along with the outdated silhouette, the colors also don't work well. The contrasting dark skirt and light blouse make the high-waisted cut appear even worse, as the skirt cuts her off harshly just below the bust. The skirt also has a metallic effect that makes the fabric look stiff and clashes with her black stockings. She would have appeared more fashionable with bare legs and a less high-waisted pencil skirt. 

Pippa Middleton made a bold fashion choice when she attended the Cheltenham Races. She wore an attention-grabbing fur hat and mustard-yellow peacoat. The style of the hat seems to be inspired by ushankas, a traditional Russian winter hat. Wearing traditional fashion pieces like this doesn't have to look outdated. In fact, they can be an excellent way to create a timeless and effortlessly chic appearance. Unfortunately, the way that Pippa styled the fur hat missed the mark. Pairing the classic Russian accessory with the more harsh yellow color of the coat makes the ensemble eye-catching but also dated. While trendy fashion colors like mustard can be fun, they run the risk of going out of vogue and aging poorly, just like this coat did.

It's hard not to compare the ensemble to when Pippa's sister, Catherine, Princess of Wales, wore a similar hat. However, Kate had the good sense to pair the fur hat with an ageless neutral coat. Kate's coat was also longer, leaning into the classic look of the hat in a way that makes it look enduring rather than out of place like it does with her sister Pippa's shorter, more trendy yellow jacket.

Along with weddings, another event you can catch royals, aristocrats, and socialites dressed to the nines for is Wimbledon. Each year, you'll catch glimpses of the royals attending the famous tennis tournament, and since they know they'll be photographed, it's a great time to make a fashion statement, like the meaningful look Kate Middleton wore to Wimbledon 2024.  Just like her sister, Pippa Middleton has had some excellent style moments at the games. But the pink dress and matching hat that she wore in 2019 will not make the list of our favorite styles. 

The summer event is the perfect time for bright, pastel colors, florals, and airy looks. Pippa went right with the pastel in this pink look, but the rest of this Wimbledon ensemble feels very dated and too stiff for the event. The tailored pink dress looks heavy and overly formal, and the gold embellishments at the collar make her look even more buttoned up. The hat was likely an attempt to make the dated style feel more current, but it has the opposite effect as, it looks out of place with the style of the dress. The wide-brimmed hat, wicker clutch, and pleated dress make her look both out of date and out of place at the sunny outdoor event. 

Attending another 2019 Wimbledon game, Pippa Middleton looked a bit more stylish in a sunshine yellow dress. Unlike the pink dress from the same year, this lighter, airy dress looked more fitting for the summer event. The dress has an adorable daisy pattern, which she matched flawlessly to small flower earrings. But while the color and fabric of the dress looked idyllic, the cut and style looked dated and led to a wardrobe malfunction. 

Rather than buttons or a zipper, wrap-style dresses like the one she wore have a front closure tied to the side. The design became popular in the 1970s and was seen for many decades after that. But in recent years, wrap dresses have become less popular. Image consultant Amanda Sanders told The New York Times, "Now you have to seek it out ... Most of the better designers don't make wrap dresses." 

Perhaps part of the reason wrap dresses fell out of vogue is that they are a common culprit of wardrobe malfunctions like the one Middleton experienced. The front tie may make the style feel effortless and airy, but it also means the garment can easily fly open to reveal far more than you planned. Middleton encountered this on the windy Wimbledon day. Her wrap dress opened to show a good portion of her upper thigh as she was crossing the street. 

Whether or not we love all of her fashion choices, Pippa Middleton has become something of a style icon, as many look to both her and her sister for sophisticated and polished inspiration. One of Pippa's favorite designers seems to be Temperly London, a UK-based brand that she's been seen wearing on several occasions. In 2011, she was seen in the front row at Temperley's London Fashion Week runway show to appreciate the designer's latest styles. But, if you were expecting a cutting-edge outfit for the fashion week event, Pippa didn't deliver.

The knee-length dress she wore was a Temperley design (per Glamour). While it was fitting to wear a dress by the designer to the show, we would have preferred to see her in a more fashion-forward piece by the brand. The cream and black dress was made of silky material with a bold, lace-like pattern over the center and trim. While lace can be very stylish, it easily looks aged, especially in this case where the dress has a lace pattern but no actual lace. The combination of the lace-like design and lightly puffed shoulders don't make Pippa look very current.

If you were hoping Pippa Middleton finally nailed her Wimbledon fashion in 2024, then you may be disappointed. The socialite attended the games with her sister Kate Middleton, and the pair looked very happy watching the tournament together. However, Pippa's style once again felt out of step. Floral patterns are excellent for summer but, when done wrong, can look more like old curtains or a couch than an excellent fashion moment. The pink dress that Pippa sported definitely fell into that trap. The long skirt and high neckline overwhelm Pippa due to the bold print. On top of that, the ruffled bust and old-fashioned ribbon around the waist start to make the garment look more like a window hanging than a stylish dress. 

This was not Pippa's first time wearing the floral number. She was also seen wearing it to her brother James Middleton's wedding in 2021. There's nothing wrong with repeating outfits, and it can be a great way to reduce waste. However, this dress was likely more stylish the first time she wore it. Only a few years later and the pink floral fabric is already feeling out of date.

Fashion is all about taking risks and making bold choices. Sometimes, those bold choices pay off, and sometimes, they end up looking a bit unfortunate. Pippa Middleton wore this daring blue dress while attending a dinner event in 2013. The bright blue number has an embellished neckline and a surprising feather skirt that definitely makes you look twice, but not necessarily in a good way. 

Both the loose silhouette, hemline, and feathery finish are reminiscent of 1920s flapper dresses. We love seeing new takes on old-fashioned styles, and the flapper dress is such an iconic moment in fashion history that it can be exciting when redone. However, in this case, it doesn't feel current. The colors and fabric choice, paired with the overwhelming amount of feathers, just seem like they're trying to do too much. The combination of blue and salmon hues in the dress with the suede blue platform heels make the look feel overdone and dated. While we'd love to see Pippa pulling off a vintage '20s style, this version of it did not suit her.