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27 Pairs That Prove This ’90s Shoe Style Is Back and Better Than Ever

Scrunchies, bike shorts, cardigans—’90s fashion mania isn't going away anytime soon, and the latest trend resurgence might just be our favorite one yet. Square-toe shoes have been popping up all over our Insta feeds and Pinterest boards and we’re officially ready to revisit the structured style. But just in case you didn’t hold on to your original pairs from 20 years ago, here are 27 brand-new shoes to add to your shopping cart asap.

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everlane square toe heels
everlane

Block Heel

These adorable slingbacks come in four glorious neutral tones.

Everlane ($165)

charles and keith plaid square toe backless mules
Charles & Keith

Plaid Mules

Paging Cher Horowitz: We found your next purchase.

Charles & Keith ($39)

gucci square toe backless slides
Nordstrom

Backless Slides

A classic that’ll stay in style for years to come.

Gucci ($790)

rejina pyo square toe strappy sandals
Moda Operandi

Dainty Straps

If you’re going to go with a ’90s vibe, you might as well embrace all the footwear elements of the decade.

Rejina Pyo ($545)


jeffrey campbell silver square toe flats
Shopbop

Ballet Flats

So you can live your best ballerina pointe shoe life.

Jeffrey Campbell ($100)

reike nen square toe pumps
FarFetch

Velvet Heels

Combine three hot trends (square toes, Mary Janes and velvet) into one killer shoe.

Reike Nen ($179)

all black square toe loafers from antrhopologie
Anthropologie

Two-tone Flats

You can never go wrong with a good old-fashioned loafer.

All Black ($159)

chinese laundry square toe heels
Nordstrom

Blush Straps

Pairs nicely with a bright and springy pedicure.

Chinese Laundry ($80)

tory burch square toe heeled loafers
Nordstrom

Chain Loafers

We’re getting major 9 to 5 vibes here, and we aren’t mad about it one bit.

Tory Burch ($358)

via spiga square toe heels
Nordstrom

Patent Black

The ideal companion to your favorite date-night ensemble.

Via Spiga ($350)

dolce vita square toe heels
Dolce Vita

Snake Print

So you can wear the animal kingdom’s best pattern all through spring and into summer, too.

Dolce Vita ($120)

kate spade new york square toe heels
Zappos Luxury

Classic Patent

They will go with literally everything in your closet. Everything.

Kate Spade New York ($228)

rachel comey perforated white square toe boots
Rachel Comey

Perforated Boots

We’re head over heels for this modern take on the Nancy Sinatra boot.

Rachel Comey ($525)


jaggar square toe wedges
Revolve

Architectural Sandals

Bonus: The semi-wedge heel and trio of straps make these much more comfortable than your average pair.

Jaggar ($162)

charles and keith square toe burgundy boots
Charles & Keith

Burgundy Boots

Sharp kitten heels balance the masculine square toe perfectly.

Charles & Keith ($69)

rafa square toe sandals
Rafa

Lilac Straps

The epitome of spring, in shoe form.

Rafa ($350)

geoz blue square toe flats
Nordstrom

Robin’s-egg-blue Flats

The patent sheen prevents these pastel beauties from looking too precious.

Geox ($160)

rag and bone square toe boots
Neiman Marcus

Black Ankle Boots

You should probably retire your old pair anyway, creating an excellent excuse for you to pick up these stunners.

Rag & Bone ($595)

leandra medine square toe flats
Shopbop

Shell Detail

We came for the versatile beige color but stayed for the charming shell ties.

Leandra Medine ($450)

jeffrey campbell red snake print square toe sandals
Revolve

Red Snakeskin

Square in the front, round in the back—this shoe is 360 degrees of chic.

Jeffrey Campbell ($125)

free people brown patent square toe mules
Free People

Heeled Mules

Introducing your new go-to weekend shoe.

Free People ($138)

roger vivier white square toe flats
Roger Vivier

White Buckles

These mod slip-ons span decades.

Roger Vivier ($725)

by far square toe heels
Net-a-Porter

Simple Straps

Soft suede and a low block heel mean these are comfy enough to wear all day long.

By Far ($370)

and other stories black woven square toe heels
& Other Stories

Raffia Heels

An excellent choice for that weird pre-spring weather.

& Other Stories ($135)

victoria beckham red square toe mules
Victoria Beckham

Bright Red Bows

Hey, if they’re good enough for Posh Spice…

Victoria Beckham ($695)

lamour des pieds square toe mules
Nordstrom

Snake Print Mules

Gold and silver flakes give this snake print a lovely subtle upgrade.

L’Amour des Pieds ($190)

public desire square toe white boots
ASOS

Stark White Boots

Worried about getting them dirty too quickly? Simply wipe them down with a leather wipe after each wear and they’ll look brand-new for much longer.

Public Desire ($56)



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Editor

Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...