Suddenly, These ’90s Shoe Trends Feel So Current

I spent the longest time running from ’90s fashion trends; my aversion to tie-dye and low-rose jeans causing almost a vitriol reaction. However, this year’s focus on the decade’s minimalist style approach has shown me that I absolutely want to be a ’90s child all over again. As my colleague, Who What Wear UK’s Editor in Chief Hannah Almassi, surmises, “The difference with this take on the ’90s is that it’s all about pared-back looks from the era. Think of the OG set including Helmut Lang, Ann Demeulemeester and Jil Sander, and you’re on the right track. It’s all plain skirts, even plainer vests, simple tailored rousers and not a scrap of makeup.” If you’re not already familiar with her impeccable style, give Carolyn Bessette-Kennedy a Google, for she encapsulates this aesthetic. 

As with all fashion trends, accessories are one of the easiest and most non-committal ways to channel them. So, we’re going to look at the ’90s shoe trends that still feel stylish by today’s standards. It’s worth noting that I’m looking at these trends through a minimalist lens, as I think they’ll have the biggest staying power in your wardrobe and won’t feel dated in a hurry. Sorry, jelly shoes. 

Scroll on to see the eight ’90s shoe trends that still feel current today. 

Style Notes: I’m not sure what it is about pointed-toe knee-high boots—probably some Pretty Woman off-shoot—but there’s something about them that feels so distinctly ’90s. Tapping into the Y2K aesthetic that’s still going strong, Balenciaga’s studded Cagole boots are one of the season’s hardest-to-find styles. However, so long as your pointed toes are razor sharp. they’ll still feel the ’90s part. Patent and mock-croc finishes with silver hardware are other key factors to consider. 

These boots are truly like gold dust this season. 

The brown colourway also feels incredibly ’90s to me. 

Style Notes: I grew up in the ’90s, so many of my shoe memories centre around heading to Clarks to buy a new pair ahead of the new school year. To this day, nothing feels more reminiscent of my childhood than a pair of chunky, Mary Jane flats. I wore mine with white socks finished with a gingham ruffle. Today, well, I’d probably still wear them with white socks finished with a gingham ruffle. 

Tap into the preppy trend by wearing your Mary Janes with a mini skirt and oversize blazer. 

The chunkier, the better. 

Style Notes: The ’90s was the decade where gym culture really snapped into gear and carrying bottled water was akin to toting the latest It bag. Now, we know better than to use single-use plastics so flippantly, but athleisure is still omnipresent. Whether working out or on your daily commute, chunky running shoes were a staple in the shoe collections of cosmopolitan women—think Ascis and New Balance. Now, fashion types are embracing the same trainers once more, wearing them with leggings then elevating the pairing with cashmere knitwear and trench coats. 

Think “dad” trainers and you’re on the right track. 

New Balance trainers continue to be one of the most sought-after in fashion circles. 

Style Notes: When I think ’90s boots, there’s one brand that always comes to mind—Dr. Martens. Although they have roots in, well, just about every British style movement since the ’60s, worn with a black leather blazer and faded jeans, they were an integral part of the ’90s uniform. The tall shaft makes them ideal for wearing under trousers, while the thick, lug-sole can take on any weather or terrain. A sage investment if you ask me. 


The high street is embracing tall Chelseas in a big way, too. 

Style Notes: Another “school shoe” that’s now the height of fashion. Who else remembers pleading with their mum to let them buy what can only be described as clodhoppers from Kickers? The rattier yours were—unravelling laces, scuffed leather—the cooler you looked in a blazer, went the philosophy. Today it’s still about wearing them with the aforementioned white socks and miniskirts.

I bought these last month and have already gotten so much wear out of them. 

Even M&S is getting in on the action. 

Style Notes: Wooden-sole shoes were are big deal in the ’90s, and wardrobe classicists couldn’t get enough of traditional clog styles. They came with high-heels and peep-toes for evening but, for day-to-day wear, closed-toe block-heels were all the rage. After enjoying a comeback in 2022, I have a feeling they’ll be just as prevalent in spring 2023. 

These look great styled with chunky marl socks for winter, too. 

Style Notes: Although platforms were a major shoe trend throughout the ’90s, there’s another heel style that was just as prevalent, though not quite as in your face. Kitten heels came into their own in the decade and were worn everywhere from the boardroom to the red carpet. Slingback styles feel particularly ’90s, and are currently cropping up in the shoe collections of every major designer, from Gucci to Saint Laurent. Though, if you’re on a more frugal budget, the high street has more than its fair share of kitten-heel slingbacks to choose from. 

My dream shoe. 

I love the angled heel on this frugal pair. 

Style Notes: Though they might have reached their popularity peak last summer, it would be remiss of me not to mention the thong mule. Almost every influencer I follow has invested them over the past couple of years, and thanks to its sleek design, I don’t see these dating any time soon. Style them with an anklet for extra ’90s styling points. 

I’m into the extra straps, which give these toe-post sandals a modern feel. 

See what I mean about patent textures feeling all the more ’90s. 

Next Up: I’m in the Mood for Something New, and These Zara and H&M Items Are It