1
Jelly Shoes
Melissa Possession Jelly Sandal
Credit: Amazon
2
Ballet Flats
Dolce Vita Reyes Ballet Flats
Credit: Dolce Vita
Wearing flats with your skinniest pair of jeans was an unbeatable combination in the early aughts. Opt for a metallic pair like these almond-toe ones for some extra shine.
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3
Platform Flip-Flops
Seychelles Skyscraper Platform Flip Flop
The bigger the platform, the more Y2K the look. These are a must for that throwback aesthetic, and this denim pair prob makes you wish for the days when all you had to do was take care of your Tamagotchi.
4
Platform Boots
Steve Madden Cobra Black
Credit: Steve Madden
The Spice Girls were all about platform boots in the late '90s, and the style only gained more popularity into the 2000s. The essential part was that the shaft of the boot was tight around your calves for a slick look with a chunky sole.
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5
Chunky Loafers
Tony Bianco Axell Loafer in Black
Credit: REVOLVE
Sensing a theme? The shoes during Y2K had some thick soles, and loafers were no different. Loafers are a classic, but the lug sole gives it some added edge. Weejuns are an editor favorite, and these happen to add an inch when you wear 'em.
6
Heeled Mules
Chelsea Paris Ace Sandal Heels
This slip-on style makes it easy to throw on, but the heel gives it some sophistication. These were everywhere on the red-carpet circuit in the 2000s, and they're still prominent now. Margot Robbie's Barbie press tour last year included lots of these styles.
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7
Kitten Heels
GUESS Dista Slide Sandal
Baby heels and babydoll dresses were a match made in heaven. The silver buckle on this Guess pair just screams Y2K, and the slight flare of the heel gives some added stability.
8
Converse Chuck Taylor All Star Hi Sneaker
High tops were a popular silhouette in the 2000s, and no brand did them better than Converse. Pop punk star Avril Lavigne had them in a regular rotation and Kristen Stewart wore them on the red carpet at the MTV Movie Awards circa 2009 during her Twilight era.
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9
Exaggerated Toes
Jeffrey Campbell Esmerelda Square Toe Mule
Heels with veryyyy exaggerated toes were a celeb go-to for fancy events, and they're undeniably eye-catching—especially a long, vamp heel that just screams Y2K. This blue mule is a perfect example of the trend.
10
Wedge Sandals
PAIGE Varya Ankle Strap Wedge Sandal
Wedges were *it* in the 2000s, and your ankles were very happy about the extra stability. If the sole happened to be made of cork or an espadrille? Even better. This strappy version from Paige would definitely fit right in if you time traveled back to the early aughts.
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11
Platform Pumps
ILLUDE High Heel Platform Pump
Ahhh, the humble hoof-like platform pumps. From red carpet events to the office, you couldn't miss these sky-high pumps during the 2000s. My toes are aching just thinking about slipping these on again, but if you're truly compelled, you can shop this wallet-friendly style here.
12
UGG Boots
Ugg Ultra Mini Classic Boot
Y2K is probably synonymous with Ashley Tisdale's High School Musical-era red carpet pics in which she's wearing UGG boots. And now it's back and better than ever! From the Tasman style to the original boot, there are tons of options that you can wear while lounging at-home or on-the-go.
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13
T-Strap Heels
Brother Vellies Olivia Pump in Midnight Nylon
This style was almost always paired with minis (think Hervé Léger's iconic bandage dresses) and most likely metallic. Today's versions are more subdued like this black pair from Brother Vellies with an optional anklet chain.
I'm Cosmopolitan's Associate Fashion Editor and write about any and all trends, major celeb fashion moments, and why wide-leg jeans are basically the best. I originally moved to New York City to audition for RENT, only to find out that the play closed 10 years ago.
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