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10 Heeled Flip-Flops That Will Make You Reconsider The Early Aughts Trend For 2020

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During the beginning of the 2000s, heeled flip-flops were the must-have shoe worn by notable names (non-fictional and fake) like Brittany Spears and Reese Witherspoon's Legally Blonde character, Elle Woods. Though they went out of style for awhile, they've been deemed trendy again, thanks to fashion-forward A-listers like Kim Kardashian and Kendall Jenner. Like other footwear styles that were once associated with being controversial (see also, dad sneakers, Birkenstocks, Dr. Martens), the fashion industry is offering a new perspective on the thong silhouette.

Designers of every caliber are giving their own unique take on the nostalgic trend by offering a grown-up way to wear heeled flip-flops. Fitted with both kitten to stiletto heels, toes both square and round, there are several colors to choose from — like, neutrals and neons. Prints aren't to be forgotten, either. Turn to New York-based label STAUD for heeled-flip flops in trendy animal motifs. The brand's Audrey Sandal, $295, combines three trends in one with its heeled flip-flop silhouette, zebra print, and square-toe. The sandal also comes in tan and brown croc-embossed, if those are more your speed. And if you want to try the trend out in a fun hue, Simon Miller has you covered. Jenner was pictured wearing the label's Beep Leather Thong Sandals in black, $390, but the shoe is also available in bright turquoise and a two-tone brown and navy blue.

If you're fully ready to embrace the nostalgic '00s trend, scroll ahead to shop TZR's favorite styles below.

We only include products that have been independently selected by The Zoe Report's editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.

Reverse Leather Thong Sandals

Marni's Reverse Leather Thong Sandals showcases an architectural iteration on the '00s trend. These unique sandals probably aren't like anything you own.

Jack Leopard-Print Leather Sandals

Not a heel person? Not to fret, the sandal comes in itty-bitty kitten heels, too. You don't have to sacrifice style for comfort with By Far's Jack Leopard-Print Leather Sandals.

Alix Croc-Effect Patent-Leather Sandals

For Sies Marjan's spring collection, the designer included a croc-effect thong sandal. Consider matching the glossy, patent-leather finish will an equally shiny lip.

Jewel Sandals

Sigerson Morrison's Jewel Sandals are a modern version of your classic pool flip-flop. Wear the rubber shoes near the water, or pair them with a casual weekend getup.

Logo-Print Metallic Textured-Leather Mules

Leave it to Balenciaga to create an ultra-luxe iteration of a heeled flip-flop. Instead of your typical stiletto, wear its Logo-Print Metallic Textured-Leather Mules to an upcoming wedding or upscale event.

Kim 40mm Thong-Strap Sandals

If you're looking for a wear-with-everything, consider Gia Couture's Kim 40mm Thong-Strap Sandals. And it's ideal for those who want a little extra height.

Beep Thong

Add a punchy pop of color with Simon Miller's Beep Thong in Wave. Pair the turquoise shoe with other vivid hues, or make it standout with an all-white ensemble.

Tippie Sandals

If you want to test out the trend before splurging, opt for Steven's Tippie Sandals, ringing in at $101. Whether you chose the black or white, they'll look chic with anything in your closet.

Audrey Sandal

Experiment with a fun animal print heeled flip-flop this summer. There's no sign of the zebra print craze slowing down, so you'll be right on-trend.

Leather Slingback Sandals

If you're worried about the lack of support a heeled flip flop provides, this style from Studio Amelia is what you need. Featuring an ankle strap, your foot isn't likely to slip out.