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Ugly Shoes: How the '90s are Alive and Well

street style   berlin   december 18, 2019
Jeremy MoellerGetty Images

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.

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THE DAD SNEAKER
The Fan Favorite: Fila Womens Disruptor II
Fila rackroomshoes.com
$64.99

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. 

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THE DAD SNEAKER
The Fashion Take: Balenciaga Triple S Sneaker
Balenciaga balenciaga.com
$975.00

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.

3 of 20
THE FLATFORM FLIP FLOP
The Fan Favorite: Rocket Dog Bigtop Black Webbing Flip Flop
Rocket Dog rocketdog.com
$39.95

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).

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THE FLATFORM FLIP FLOP
The Fashion Take: Fendi Flatform
Fendi fendi.com
$690.00

The bubble gum pink reinterpretation of this retro shoe takes the nostalgia of this style to even higher heights.

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THE SUPER-TALL SNEAKER
The Fan Favorite: Buffalo Rising Tower
Buffalo buffalo-boots.com
€99.90

Baby Spice's shoe of choice, enough said. 

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THE SUPER-TALL SNEAKER
The Fashion Take: Stella McCartney Eclypse touch-strap sneakers
Stella McCartney farfetch.com
$765.00

Stella McCartney must have designed these with one fellow Brit in mind.

7 of 20
THE GRANOLA GO-TO
The Fan Favorite: Birkenstock Arizona Sandals
Birkenstock shopbop.com
$135.00

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.

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THE GRANOLA GO-TO
The Fashion Take: Birkenstock Arizona Proenza Schouler
Proenza Schouler birkenstock.com
$420.00

The stoners who listened to Phish in high school grew up and now are wearing these (please note the price!).

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THE WONKY HEEL
The Fan Favorite: John Fluevog Mega Munster Original
John Fluevog fluevog.com
$355.00

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. 

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THE WONKY HEEL
The Fashion Take: Amina Muaddi Gilda Glitter Slides
Amina Muaddi intermixonline.com
$855.00

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.

11 of 20
THE RAVER HIKER
The Fan Favorite: Skechers Womens Shindigs
Skechers rackroomshoes.com
$59.99

Just add UFO pants and a baby tee. 

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THE RAVER HIKER
The Fashion Take: Miu Miu Lug Sole Hiker Booties
Miu Miu neimanmarcus.com
$850.00

This Miu Miu pair is a bit more refined take and the gingham laces keep the style connected to its playful past.

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THE MINIMALIST SLIDE
The Fan Favorite: Steve Madden Slinky30
SteveMadden stevemadden.com
$92.95

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. 

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THE MINIMALIST SLIDE
The Fashion Take: Gianvito Rossi Bekah Platform Sandals
Gianvito Rossi thewebster.us
$465.00

The strappiness of this modern take somehow make platforms feel a bit sexier and more grown-up. Still bitchy though.

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THE MARY JANE SLIPPER
The Fan Favorite: Cotton Mary Jane Slipper
pearlriver.com
$16.50

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. 

16 of 20
THE MARY JANE SLIPPER
The Fashion Take: Mary-Jane canvas platform flats
Prada matchesfashion.com
$523.00

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.

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THE OUTDOORSY SANDAL
The Fan Favorite: Teva Hurricane XLT2
Teva teva.com
$70.00

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. 

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THE OUTDOORSY SANDAL
The Fashion Take: Gucci Aguru sandal with crystals
gucci.com
$320.00

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.

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THE GOTH MARY JANE
The Fan Favorite: Dr. Marten Bethan Mary Jane
Dr. Marten drmartens.com
$150.00

This chunky platform mary jane style is a '90s staple from the ever-classic Dr. Marten. (Depeche Mode CD not included).

20 of 20
THE GOTH MARY JANE
The Fashion Take: Burberry Aldwych Mary-Jane flats
Burberry matchesfashion.com
$680.00

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.

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