Outdated Heel Trends We Caught Celebs Wearing On 2026 Red Carpets

This award season has been quite something, with Hollywood's rich and famous making headlines for their questionable red carpet looks. From head to toe, some celebs were accused of having "Ozempic face" while others stepped out wearing outdated heel trends. The year 2025 marked the resurgence of ballet flats, largely thanks to Miu Miu, but so far, heels have proven to be irreplaceable, as personal stylist and creator of Your Style Transformation Academy Cynthia Kennedy suggested in an exclusive interview with Women.

As women continue to reject the gender stereotype that defines a feminine woman as one who wears heels, it's getting harder to find a style of heel that pleases everyone. "[Hight heel pain] seems like a distant memory of the pre-pandemic days and something the majority of women refuse to endure for the sake of how something looks," Kennedy told us, alluding to how "beauty is pain" is very much out in 2026. 

Along with high heels, some other styles that should be swapped out in 2026 include embellished, strappy, and pointed heels. Metallic and transparent heels are also considered outdated. What's more, minimalism is out and maximalism is in — but not overdone. Peep-toe heels are also out of season, unless they are worn correctly. So far, not so good. With the 2026 Met Gala fast approaching, fashion experts can only hope that celebrities get it right next time, or turn up to the carpet looking slightly more grounded.

When Li Jun Li walked the red carpet at the Golden Globes, the media couldn't stop eyeing her sky-high stilettos. However, while Li looked incredible, personal stylist Cynthia Kennedy told Women that sky-high stilettos are considered outdated in 2026. "Now, women want designs they can wear all day," the fashion expert said. "They're no longer willing to suffer for the look of a sky-high stiletto." Kitten heels, a popular heel choice for older women, have replaced high heels, especially in the office. 

While speaking to Women, personal stylist Cynthia Kennedy described transparent heels as "out of place and unbalanced." Despite their impracticality, Karol G looked comfortable when she arrived at the 68th Grammy Awards in a pair of PVC heels. While Victoria Beckham tried to bring the clear style back in 2025, Dr. Rock Positano told British Vogue that the shoe "provides a perfect milieu for fungal growth" — not so chic. Thankfully, the audience was too compelled by Karol G's sheer dress to notice the footwear, topped with fringe and lace detailing.

The silver-toned heels worn by Jennifer Aniston at the Actor Awards have been returning to the fashion scene since the style became a trend in the 1970s. Glamour dubbed metallic footwear "the shoe of Paris Fashion Week" in 2012, making a return in 2022 and again in 2023. However, Indian designer Troy Costa told Hindustan Times that silver finishes can look outdated if not paired with "plain" items. Considering Who What Wear also agrees that gray shoes are outdated, it seems their time may be coming to an end.

Minimalist shoes are fading out as maximalism comes back in 2026, though singer-songwriter Tyla may have missed the memo with her pair of plain, nude heels for the Grammy Awards. Natalie Tincher, principal stylist and founder of BU Style, told Business Insider that minimalist styles are being overtaken by statement shoes. "Bold prints like zebra or leopard, and even more adventurous materials" are making a comeback, the expert said. Vogue Arabia also reported that "we've entered our more-is-more era" with accessories too.

When English singer-songwriter FKA Twigs stepped onto the Grammy Awards red carpet wearing a pair of platforms, it felt very 2023. Platform heels really had their moment back then, when they were seen on the likes of Kendall Jenner and Paris Hilton at the Met Gala. According to personal stylist Cynthia Kennedy, platforms are on the way out in 2026. "Today's styles are much more refined, having slimmer profiles, intentional proportions, and sculptural or angled features," Kennedy told Women.

At the Actor Awards, Regina Hall looked striking in an ornate gown, but her embellished silver heels were questionable. Fashion stylist and lifestyle expert Joseph Katz exclusively told Women, "Overly embellished shoes drenched in crystals and heavy metallic hardware are taking a step back." Embellished shoes are becoming old fashioned as creative directors are putting a "continued emphasis on versatility and wearability," Katz added.

Everybody knows that Bridgerton's Adjoa Andoh, who plays Lady Agatha Danbury, is a force to be reckoned with on and off screen. However, her strappy shoes at the Actor Awards make the list for being outmoded. According to personal stylist Cynthia Kennedy, strappy designs are "falling out of favor" and "streamlined, simplified designs are taking over instead," the expert told Women. However, the personal stylist reassured us that Velcro-straps are still trendy. "They're practical for all-day wear but still look cool and intentional," she said.

Blackpink's Rosé looked frightfully fantastic at the BRIT Awards in a leggy, black gown and pointed, white stilettos. The lengthy slit of the dress that put the singer-songwriter's shoes on display was mostly viewed as a success, but some fashion experts begged to differ. Personal stylist Cynthia Kennedy told Women that pointed heels "can appear harsh and too severe." Furthermore, fashion business consultant Dr. Carolyn Mair told CNN that women have started to "reject footwear that may limit mobility and comfort."

Peep-toe heels are outdated in 2026, unless worn right. Fashion experts would say that Jenna Ortega was wrong when she wore open-toe heels to complement her already-captivating dress at the Actor Awards. Personal stylist Cynthia Kennedy told Women that peep-toe heels should be a statement that stands out on their own. "The new peep-toe is not about stacking trends or over-accessorizing. It's about letting the shoe feel like part of a cleaner, more intentional look," Kennedy explained. On the red carpet, Ortega's busy dress only overshadowed the peep-toe heels.