Recently, while I was looking back through old photos of myself for this story another editor was pulling together about outfits from the 2000s, I made an important discovery: The shoes I was wearing in the late '90s were actually... cute? Not for their classic timelessness, but for the simple fact that I'm old enough now to have these styles come back into fashion after taking a 20 year break. Yikes. But, before this generation of tastemakers stake claim in these styles, let's take a moment to recognize these ugly shoe icons. Street footwear in the '90s was not all "Gwyneth Paltrow simplicity," it was loud and disruptive with chunky silhouettes or shoes so flat they did just about nothing for your legs. However, I will forever stand by my adolescent shoe choices and celebrate their return back into the spotlight. Scroll down to see the shoes that popularized the genre and fashion's new interpretation of these wacky but wonderful shapes.
It's hard to pinpoint the actual origin of the Dad Sneaker and its modern day resurgence, but it's safe to say the Fila Disruptor has the chunkiness and the height to make it super covetable.
Some might call these the "Granddaddy" of all Dad Sneakers, the Balenciaga Triple S (named for the 3 soles layered on top of one another), is fashion's ultimate answer to this '90s style.
Ask any boardwalk surf store owner in 1998 and they'll tell you these were the shoe of the summer (besides an air cast when one inevitably rolled one's ankle while wearing them).
The bubble gum pink reinterpretation of this retro shoe takes the nostalgia of this style to even higher heights.
Baby Spice's shoe of choice, enough said.
Stella McCartney must have designed these with one fellow Brit in mind.
If you were a stoner who listened to Phish in high school and didn't have these, then you weren't a stoner who listened to Phish.
The stoners who listened to Phish in high school grew up and now are wearing these (please note the price!).
As the '80s and '90s club kid staple, John Fluevog is the pioneer of the ugly shoe. He still keeps the whimsy alive 50 years later with 28 stores worldwide.
Shoe designer Amina Muaddi can barely keep her bold designs in stock after gaining major clout as Rihanna's shoe designer for her line, Fenty. As a designer she pushes shape and proportion and her wonky heel has become a signature of her namesake line.
Just add UFO pants and a baby tee.
This Miu Miu pair is a bit more refined take and the gingham laces keep the style connected to its playful past.
What is a '90s shoe roundup without Steve Madden? The Slinky (re-released as part of a 30th anniversary) was the quintessential bitchy high-schooler sandal.
The strappiness of this modern take somehow make platforms feel a bit sexier and more grown-up. Still bitchy though.
Before they were sold by the buckets-full at Urban Outfitters, these simply constructed and highly affordable cotton (and velvet) mary janes came from Pearl River Mart, New York's iconic Chinese import purveyor.
The simplicity of this mary jane gets the quirky Prada treatment with a hybrid sole of espadrille and sneaker tread to make it a perfect mix of classic styles all in one shoe.
Just as cool on its own as it is with a pair of wool camp socks, the ever-technical Teva style is a classic for rugged living.
This is the outdoorsy sandal for someone who is... not very outdoorsy? We'll just say they're great for stomping through the concrete jungle instead of an actual one.
This chunky platform mary jane style is a '90s staple from the ever-classic Dr. Marten. (Depeche Mode CD not included).
Riccardo Tisci's take on Burberry since his 2018 appointment as chief creative officer has drawn inspiration from British high society as well as counter culture, as demonstrated here in these shoes.