'90s Shoes That Have Us Totally Buggin'

The dream of the '90s is alive in your closet.

sandana jelly sandal

Salter House

I will never forget a road trip my family took in the '90s where my jelly shoes broke and we ultimately wound up in search of a replacement pair. I loved my jelly shoes. They completed my outfit in a way no other shoe could (mind you, I was 5). There are a group of shoes from the '90s that have this iconic irreplaceable element to them that makes them really complete an outfit. If you look at any ode to the '90s Instagram account (@90sanxiety, @90smilk, there are so many), the shoes really complete so many of the outfits referenced. Today, in 2021, we are seeing a resurgence of these styles, and for a good reason! For a kick of nostalgia and an essence of that '90s coolness, I’ve rounded up 12 styles to slip your feet into and march back in time in.

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My jelly shoes looked exactly like the ones Melissa makes, seen on the street in downtown NYC. They add a dash of playfulness to your outfit, which is why I particularly enjoy them worn with a suit or something very classic and sharp. I love that contrast. You don’t have to go for the literal caged pair from your childhood, these shoes go upscale, too. Designer brands have even taken to this trend with Gucci’s block heel platform and this sleek mod pair from Ancient Greek Sandals in collaboration with Harley Viera-Newton. 

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Platform Wide-Strap Slap Sandals

I won’t exhaust this roundup with Steve Madden, but these platforms—the ones that slapped your heel and were worn by moms and daughters alike—are an iconic '90s style that is certainly back. Balenciaga even came out with a pair that is the spitting image of Steve Madden’s original. You can now find shoes with that fun, easy, cool silhouette. I personally love the modern black and white pair from Sincerely Tommy and the Instagram-famous pair from Lisa Says Gah. But the original pair that makes that really satisfying slap sound when you walk, now available in a slew of other shades, still owns my heart.

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Heeled Thongs

I’m focusing on two really iconic '90s thong sandals styles: the platform and the heel. The platform version—similar to the “slap” platform—is playful, fun and casual, sometimes even sporty. The heeled version is a cool shoe to dress up jeans or pair with a dress. They’re one of my favorite heeled sandals on the market right now. Maybe it’s my love of the '90s.

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Birkenstock Style

We’ve been wearing these for years—designer brands such as Jil Sander, Proenza Schouler, Rick Owens, Valentino, and Too Good even saw the consumer love for the shoe and collaborated with the Birkenstock brand to make high-end styles. If you were a Gap kid, perhaps you remember this Gap commercial from the decade where everyone is in a black pair of Birkenstocks Boston clog-style shoes. The Birkenstock clog is a cool '90s style that, by the way, pairs really well with a tube top. 

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Heeled Loafers

One of my favorite shoe styles from the '90s is the heeled loafer. They are typically a bit chunky, and always have a distinct block heel. I wore a pair of these in a grey fabric by the brand Candies in 1st grade, and believe me when my six-year-old self tells you they make you feel very, very cool. To this day I wear a pair from Vagabond or another from Labucq regularly, and I have always very much loved the epic Gucci pair with the horsebit buckle.

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Perhaps the surge of Keds in the 1990s was the aftermath of the late-'80s epic Dirty Dancing—that’s what drew me to them at least—but Keds are a timeless sneaker you’ll commonly see today. They’re a hybrid between a sneaker and ballet flat, making them great for dancing. They pair well with leggings ('90s!) and tennis skirts alike. They also come in wide sizing, since they do tend to run a bit narrow! 

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Combat Boots

I would never consider Dr. Martens as “out” of style throughout my 29 years on this earth, since you can pretty much guarantee seeing them on a foot in NYC at any time of the year. According to Complex though, '90s kids in the U.K. made them huge as the “indie” boot. If you don’t own a pair, the combat/military boot happens to be really versatile. Designer brands have even sunk their nails in with high end brands like Bottega Veneta, Louis Vuitton, Balenciaga, and Hèrmes making their own versions. In my opinion, good old Dr. Martens do the job. These boots can make your trousers look a bit cooler, add some weight to a mini skirt, and also pair really well with baggy jeans (or folded over overalls) à la Rihanna. Dr. Martens even makes platform (and suuuuuper platform) styles, if you want to really lean into the '90s. 

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Chunky Sneakers

By no means do I know my sneaker vocabulary, and I know that there are a ton of iconic styles from the '90s. I personally am drawn to the sneaker style like those Princess Diana wore iconically; a high-top Reebok style. The idea here is that the sneaker should start your outfit.

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Puffy “Floaty” Sandals

Do you remember Sugar Floaties? I honestly remember wanting to bite them. They were so squishy and plush and delightful. Practical? No. But they certainly did float, which was cool as a kid. Today, we’re seeing shoes I’d want to wear as an adult with a similar puffy body. I love these by Ugo Paulon which I found through Mecca James-Williams' Instagram. Each shoe is handmade and one of a kind using upcycled materials. I also enjoy these from Staud. Very much “Sugar Floaties” vibes, though I’m not sure if they float.

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Heeled Mary Janes

I’m not sure why I waited this long to address heeled Mary Janes, because they’re a favorite style of mine. I find them comfortable enough to walk in, but sophisticated enough to still feel thoughtful. A heel though? It oozes '90s and I love it. We have the Nodaleto Bulla Babies Mary Janes that are certainly an ode to the '90s or at least Drew Barrymore. I cannot confirm any details about them because I don’t own them myself, but I look at them a lot. My favorite ones I personally own were purchased on sale at Urban Outfitters years ago.

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Dr. Scholls

I honestly remember being semi-horrified by the look of these shoes when my mom wore them in the '90s, but two years ago I found myself featuring them in an editorial. I guess it’s called maturing? I actually got a pair from the '90s off of Etsy because they look a bit different than the ones being produced now. If for nothing else, these shoes—originally designed in the '60s—are easy dog walking shoes and they’re still turning heads in Milan.

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Feathers and Floof

These are here for nothing other than pure joy. I love shoes and have loved them since I was a shoe size two, wearing plastic slippers with feathers on them out of the house. They completed my outfit! Today, brands keep the magic of those fun feather shoes of our storybook-filled childhoods alive. You will today see women wearing Brother Vellies’ infamous Paloma style out in their cocktail attire. These '90s childhood staples live on (and are no longer plastic). Just check the forecast before you wear them.

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