When we think about the most iconic heel trends of that bold, fashion-forward decade, many immediately picture the classic kitten heel. But the era offered far more variety, spanning distinct silhouettes and moods—from understated minimalism to striking maximalism. The ’90s delivered unforgettable designs from fashion heavyweights like Chanel’s two-tone pumps, Miu Miu’s geometric loafers, and Prada’s Mary Janes. Today, these nostalgic shapes are re-emerging with a modern twist, making them feel fresh, relevant, and essential once again.
Although the spring 2026 runways showcased experimental designs—think Proenza Schouler’s bow heels, Bottega Veneta’s sculptural clogs, and Balenciaga’s edgy ballerinas—it was undeniably the ’90s-inspired heels that dominated. Their appeal lies in their effortless elegance, ability to add subtle interest, and versatility. These styles elevate a simple jeans-and-tee outfit just as easily as they enhance the allure of a mini dress. It’s no surprise they were beloved by the era’s top supermodels.
While hunting for authentic vintage pieces remains a great option, many modern brands are offering updated interpretations of these iconic designs. Below are the six standout ’90s heel trends defining the season.
Six ’90s Heel Trends Leading 2026 Fashion
Two-Tone Pumps
Two-tone heels are firmly back in the spotlight, thanks in large part to renewed interest sparked by Matthieu Blazy. Chanel cemented this style in fashion history during its spring 1992 collection, when Linda Evangelista opened the show in a refined black-and-white pair. Decades later, these pumps remain timeless. Choose classic pointed or triangular toe shapes and style them with tailored suits, structured dresses, or update the look with straight-leg denim.
Pointed Heeled Mary Janes
Mary Janes often get labeled as youthful, but the ’90s proved they can be elegant and feminine. Prada’s sharp-toed and wedge versions transformed the silhouette into something polished and chic. A favorite of Christy Turlington, this style still graces the streets of Milan and Rome. Their refined structure pairs beautifully with shift dresses and midi skirts, transitioning seamlessly from day to night.
Heeled Colorful Loafers
Nostalgia remains a driving force in footwear, though designers are adding bold updates. Gucci recently revived its iconic ’90s loafers—famously worn by Helena Christensen in 1995—featuring square toes, chunky heels, and jewel-toned hues. The modern versions push proportions further with elevated platforms, making them ideal for adding drama to mini dresses, micro shorts, flared trousers, and short skirts.
Heeled Mules
If one shoe truly defines the ’90s, it’s the heeled mule. This minimalist sandal became a staple thanks to supermodels like Kate Moss and Cindy Crawford. Its enduring popularity comes from its versatility and clean design, making it just as relevant now as it was then.
Square-Toe Pumps
Square-toe heels are impossible to overlook. Known for their sharp lines and subtle masculine edge, this silhouette has been reimagined by brands like Miu Miu, Prada, and Alexander McQueen. Style icons such as Kendall Jenner, Rosalía, and Daisy Edgar-Jones frequently wear them with tailored trousers or classic denim for a polished yet relaxed look.
Transparent Heels
No discussion of ’90s footwear is complete without transparent heels. Both controversial and iconic, they captured a specific minimalist aesthetic that dominated until the early 2000s. Chado Ralph Rucci’s spring 1999 collection featured a bold version with exposed toes and a clear block heel. Today, designers like Vetements and Maison Margiela are bringing this sensual, statement-making style back into focus.
