Nostalgia Alert: These 90s Shoes Trends Were So Cool Beans

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4 women wearing 90s style shoes

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Shoes in the 90s were interesting, to say the least. We had sleek little strappy sandals, but we also had inexplicably high platform sneakers. We had chunky Docs alongside glittery, translucent jellies. Honestly, you can study an entire decade by focusing on the ankle down!

Here are the most popular shoes from the 90s. Time for nostalgia! 

1. Jelly shoes 

Transparent, often glittery, gummy-textured sandals with buckles and basket-weaves. If you were lucky, you had the heeled jelly shoes. Everyone from babies to full-grown students wore these whimsical foot confections. 

How to style:

  • Pair jellies with cropped Ponte pants and a crisp white shirt for sophisticated-meets-playful 
  • Pair heeled jellies with denim overalls over a tank 
  • Throw heeled jellies on with a satin bias cut slip dress for going out 

2. Steve Madden slides (‘slinky’)

These were a staple for teens, tweens, and on-trend grown-ups in the 90s. A platform sole with a stretchy black upper and open toe. Simple. Clunky. 90s. 

How to style: 

  • Wear with cropped jeans and a bodysuit or tucked-in tee
  • Wear with a bias-cut midi skirt and cotton ribbed tank 
  • Wear with a satin slip dress and cropped wrap cardigan (like Lorelai Gilmore)

3. Chunky Fila sneakers

Chunky sneakers like The Disrupter 2 sneakers by Fila were peak cool in the 90s. Dads would wear them with jeans and fanny packs. Cool kids would wear them with denim midi-skirts, overalls, or tearaway track pants and crop tops.

How to style:

  • Wear with opaque tights and a cord mini dress for winter
  • Wear out with a white shirt and embellished skirt 

Read: 11 Lesser Known Celebrity Fashion Moments of the 90s

4. Adidas slides

Who didn’t own a pair of Adidas slides? Take a look around next time you’re out and you’ll surely see a few as they’re back. Classic white and navy stripes, sometimes with a velcro crossover. 

  • Go quirky with slides over socks 
  • Pair with cropped jeans and a loose linen shirt 

5. Embellished mesh slides

These were huge in the early 00s as well the 90s and were found everywhere from high-end clothing shops to dollar stores. A round-toe, mesh slide with little flowers made from clusters of sequins. 

How to style: 

  • Wear a bright shade with a simple wrap mini dress in summer
  • Wear with high-waisted blue jeans and a tucked-in white tank in spring 

6. Doc Marten combat boots 

Rockers, grungers, and angsty teens wore Doc Marten (or off-brand) combat boots throughout the 90s and beyond, often with plaid and ripped denim. They even made their way into a poem in ‘10 Things I Hate About You’ (“I hate your big dumb combat boots!”). 

How to style: 

  • Juxtapose rough with sweet by pairing with a bias-cut midi dress in floral satin
  • Pair with flared jeans and a tucked-in fitted band tee (70s/90s mash-up!)

7. Spice Girl-style Buffalo Platform Sneakers

The Spice Girls dancing around in tiny mini dresses and sneakers with excessively large platform soles. An image synonymous with 1990s pop culture. How were more ankles not broken?!

How to style:

  • Try a creeper style or slightly smaller platform for safety and wearability
  • Pair flatform sneakers with a sports-style mini skirt and tee 
  • Pair with straight-leg jeans and a long-sleeved bodysuit 

8. Kitten-heel strappy sandals

Heading to prom or a date in the 90s? You’d better get a pair of strappy kitten heels to go with your double-layer slip dress. The heels must be short, the straps must be plenty. 

How to style:

  • Go full 90s sweetheart with a chiffon midi dress and sequin bolero
  • Pair with skinny jeans and an embellished off-shoulder top for drinks out 

9. Chunky leather sandals by MIA 

Picture basket-woven leather, an open toe, a blocky heel, and a raised sole. Secured with a buckle at the ankle, and usually in deep brown or black. 

How to style:

  • Wear with a floral sundress and denim jacket for weekend gallivanting
  • Pair with a sleek midi skirt and crisp shirt and jacket for work 

10. Nike Air Force V

The chunky sneakers were the fifth version of the iconic baller shoes first released in the early 80s. AF V’s had high tops and plenty of street cred. 

How to style:

  • Wear with opaque tights and a denim wrap dress in winter
  • For summer, throw on with denim culottes and a white tank 

11. Clunky heeled loafers

Rachel Green from ‘Friends’ was known to wear heeled loafers with chunky heels, often with mini skirts and fitted tees. They certainly weren’t dainty, but they were cute and a little scholastic. 

How to style: 

  • Copy Rach and wear with tights, a black mini, and turtleneck sweater
  • Wear with a structured jumpsuit and blazer for work 

12. Platform flip-flops

Check out the ‘10 things I hate about you’ poster, 90s Gwen Stefani, and Rachel in early ‘Friends’ episodes and promo shoots. You’ll see flip-flops with platform soles worn often with Mom jeans or boot-cut trousers. Hmm or mmm?

How to style: 

  • Wear with a one-piece swimsuit, resort tee, and sarong to a 90s pool party
  • Pair with straight-leg cords and a worn-in band tee and denim jacket 

13. Birkenstocks

Supermodels wore Birkenstock sandals in the Marc Jacobs for Perry Ellis grunge show in 1993. The comfy leather sandals were (and still are) earthy, comfy, grunge-meets-European-traveller, and timeless. 

How to style: 

  • Wear with a slip dress and cropped bolero cardigan
  • Be authentically 90s cute-girl with Birks and ruffle-top socks
  • Pair with worn-in blue jeans, a fitted racer-back tank, and khaki jacket 

14. Adidas Superstar sneakers

Run DMC made Adidas Superstars iconic, with the round toe, low top, and triple stripe. They’re still just as favored today, seen on Rihanna, Zendaya, Jay-Z, and countless other glitterati. 

How to style:

  • Wear with button-side track pants and a simple tank for weekend pottering
  • Wear with cigarette trousers and a cowl-neck satin top for Saturday drinks 

15. Heeled Mary-Janes

The girls on ‘Clueless’ totaled around wearing knee-high socks, mini skirts and heeled Mary-Janes. Round toes, shiny finish, blocky heels, and straps across the ankles. Demure yet sassy. 

How to style: 

  • Wear with opaque tights, an a-line mini skirt, and a turtleneck sweater for cute weekend brunching 
  • Pair with raw-hem cropped jeans and a worn-out graphic tee for sweet-vs-edgy

16. High-top lace-up boots with padded tops

Angela on ‘My so-called life’ and many real-life angsty teens wore lace-up boots with high tops up to the lower calf. They were ultra worn-in, kinda sloppy, and adored day after day, no matter the outfit. 

How to style: 

  • Pair with tights and a dark denim midi-dress and a cropped leather jacket for casual workdays
  • Pair with a long-sleeved floral wrap mini and ribbed tights for weekends 

Inspo Corner: Jacket Throwback Ideas

17. Knee-High Boots 

Knee-high boots, often with a square toe, were popular in the 90s. Hilary Banks (from ‘Fresh Prince’) and the Spice Girls famously wore the style, often with mini skirts or babydoll dresses. 

How to style: 

  • Pair with sheer stockings, a sleeveless shift dress, and a bolero cardigan
  • Wear with an a-line mini skirt and roll-neck bodysuit with an oversized blazer 

18. Reebok Classic sneakers

Reebok classics sneakers were a favorite sneaker in the 90s, in various shades and versions. Favored by Dads, teens, students, and hip-hoppers.  

How to style: 

  • Wear with classic blue Levi’s 501s and a grey marle tank
  • Wear with a ribbed cotton midi dress and denim jacket

19. Converse All-Stars and One-Stars

Converse lace-ups were a key ingredient in 90s outfits for everyone from grunge bands to skate kids. Skip forward to today and black-and-white Converse are on the toes of ultra fashion stars like Kate Moss and Kaia Gerber. 

How to style:

  • Wear with pleated suit trousers and a tucked-in white tank for “weekend smart”
  • Wear with a denim mini dress and a white tee for weekend casual
  • Be a rebel at work with a black pencil dress, blazer, tights, and Converse 

20. Satin point-toe pumps

90s Oscar night red carpets were a-flutter with satin pump heels with pointy toes. Now considered slightly out-dated, they were often worn with satin gowns with corseted waists and princess skirts. 

How to style: 

  • Embrace the satin heel for daily wear with raw-edge jeans and a linen shirt
  • Pair with a black wrap mini and loose-fit shirt (French tucked) for nights out 

21. Black open-toe strappy heels 

Take a look at the promotional photos from the first ‘Sex and the City’ seasons (‘98 and ‘99) and you’ll see a plethora of black strappy sandals. Open-toe, often kitten-heeled, totally 90s. 

How to style:

  • Pair with a midi wrap skirt and Bardot top for weekend dates 
  • Pair with a slim-leg jumpsuit and cropped leather jacket for work-to-drinks

22. Skechers Roadies

Skechers Roadies were a very tame version of the platform sneaker, with enough chunk to elevate you, while remaining safe. Often in deep red, black, or navy with contrast white stitching. 

How to style: 

  • Wear with white tube socks, baggy cargo pants, and a crop tank 
  • Pair with a midi skirt, white tank, and cropped indigo denim jacket 

23. Fluffy slip-on heels 

 

Who had a pair of these when they were about 5? Little plastic slides with gaudy glitter, age-inappropriate heels, and fuzzy fluff? You would also find them with satin chemises in ‘Victoria’s Secret’. 

How to style: 

  • Instead of fluffy heels, try fluff-trimmed socks with pumps instead 
  • Look for heeled booties with fur lining for a more robust approach 

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