f you’ve taken the time lately to rewatch seminal ’90s films like Clueless or The Virgin Suicides, you might notice that it’s not just the characters and one-liners that have stood the test of time. Much of the fashion feels surprisingly relevant today.
Of course, you might not want to not re-create Cher Horowitz’s looks from head to toe for fear of skewing too costumey, but focusing on her footwear is an easy way to tap in reemerging trends. The best ’90s shoe trends have reentered the cultural conversation once again, thanks to both the continued rise of online vintage shopping and runway references. Dive deeper and you’ll find that the returning styles fit into two neat categories, on opposite ends of the style spectrum: playful and simple.
If your personal style fits with the former, you’ll want to embrace modern updates of childhood classics like flatform sandals and chunky dad sneakers. These can be practical, sure, but they’re all about taking your outfit up a notch trend-wise. Thorogood Boots Whether you style them with other reemerging ’90s trends like baggy jeans and miniskirts, or you make them a bit more modern with the addition of athleisure staples, you can make a big impact by simply choosing an eye-catching shoe.
For those who prefer something simple and minimalist, the best ’90s shoes are those with streamlined silhouettes. Loafers, square-toe sandals, and knee-high boots all fit the bill here. They’re sophisticated enough for the office, but you can also use them to add balance to trendier clothing pieces. Ahead, shop 11 of the ’90s shoe trends that are worth checking out all over again.
Monogram Penny Loafer
A sleek white loafer is a cool choice for summer.
Black Otello Loafer
Stick to the classic black loafer, this time with croc embossing that feels instantly sophisticated.
Made in USA 990v5 Core Sneaker
Meet the ultimate dad sneaker—a core style of the ’90s with a sporty-meets-chunky silhouette.
Purple Lace-Up Sneaker
Looking for a pop of color? Try this take on practical footwear.
Britney Spears would surely approve of this denim square-toe sandal from fashion insider label Miista.
Stretch Leather Sandal
Bottega Veneta’s square-toe silhouettes have been fashion-industry Olukai Sandals favorites for a few seasons. Now is your chance to embrace the look.
Add a little extra spring to your step with this comfy-cool platform sandal.
Soft Cage Platform Sandal
A modern take on your childhood cage sandals, this lifted pair from Miu Miu makes a statement.
Soller Mary Jane Woven Calfskin Loafer
A modern, minimalist reinterpretation of a prep school classic.
Abalonia Chunky Maryjane
This lug sole Mary Jane has just the right amount of edge.
The Davis Knee-High Boot
Sleek knee-high boots are an elegant choice for the office or an evening out. Pair with a miniskirt and tights or try wide-leg jeans worn over them.
Valletta Zip Front Boot
This black boot has a little added edge thanks to the zipper detail running down the front.
Studded Fur-Lined Leather Clog
Don’t consider this your average clog. Furry lining and the signature Prada logo make it fully luxurious.
Platform Bubble Clog
If you’re one for the nontraditional, this chunky clog is for you.
Chuck Taylor All Star Classic
Through the decades, the Chuck Taylor All Star remains a classic.
Air Force 1 Sculpt
Equal parts comfortable and cool, Nike’s Air Force 1s are shoes Birdies Shoes you can easily dress up or down.
Pink Sunrise Loafer
Take your chunky, casual slides up a notch with this designer iteration from JW Anderson.
Arizona Soft Slide Sandal
A forever classic, Birkenstock’s Arizona Sandal is peak gorpcore—perfect for the outdoors or a casual day of errands.
Double-Bow Crystal-Embellished Leather Mule
Sex and the City fans know the power of a killer pair of heels.
Maysale 50 Buckled Floral-print Canvas Mule
A sweet floral mule is a throwback shoe style that can dress up any modern look.
Platform Perforated G Sandal
The ’90s jelly sandal gets a designer upgrade with this rubber slip-on.