The 2000s were a wild time for fashion, and shoes? Oh, they were a whole thing. From sky-high stilettos to bizarre platform flip-flops, the decade delivered some of the most memorable celebrity footwear moments ever.
Whether it was on the red carpet, at the club, or in a paparazzi shot with a Frappuccino in hand, these shoes weren’t just accessories—they were fashion statements that defined an era. Some were chic, some were questionable, and some were just straight-up painful to look at.
But no matter what, these shoes left a mark on pop culture. So, let’s take a strut down memory lane and relive the 15 biggest celebrity shoe moments of the 2000s—because love them or hate them, you know you remember them.
1. Carrie Bradshaw’s Manolo Blahnik Hangisi Heels in Sex and the City (2008)
We can’t talk about 2000s shoe moments without mentioning the blue satin Manolo Blahnik Hangisi pumps. When Mr. Big proposed to Carrie Bradshaw with a pair of designer heels instead of a ring, the shoe became instantly legendary.
These sparkly, sophisticated, and ultra-luxe pumps basically cemented Manolo Blahnik as the go-to designer for fashion girls everywhere.
2. Paris Hilton’s Hot Pink Pumps (Every Club Appearance Ever)
Paris Hilton was the ultimate 2000s It Girl, and so were her shoes. Whether she was rocking a Juicy Couture tracksuit or a sequined mini dress, she was always in sky-high, hot pink stilettos. Bonus points if they were Dior, Jimmy Choo, or covered in rhinestones.
3. Beyoncé’s Futuristic Silver Pumps at the 2003 BET Awards
Beyoncé’s metallic silver pointed-toe pumps at the 2003 BET Awards were peak early 2000s. They were sharp, shiny, and just a little bit extra, perfectly complementing her bejeweled mini dress. The 2000s were all about matching metallic accessories, and Bey delivered.
4. Britney Spears’ Platform Flip-Flops (2002-2005)
Britney Spears was the queen of Y2K fashion, and nothing screams early 2000s more than platform flip-flops. She was frequently seen wearing them with low-rise jeans, a crop top, and a Starbucks Frappuccino in hand. Uncomfortable? Probably. Iconic? Absolutely.
5. Jennifer Lopez’s Timberland Heels in “Jenny from the Block” (2002)
J.Lo took street style to new levels when she wore Timberland-inspired high heels in her Jenny from the Block music video. These camel-colored, lace-up boots with a high stiletto heel were both practical and absurd, making them so early 2000s. And honestly? We’re still thinking about them.
6. Christina Aguilera’s Knee-High Lace-Up Boots (2002 VMAs)
The 2002 MTV Video Music Awards were rife with unforgettable fashion choices, but Christina Aguilera’s ensemble stood out prominently. She donned striking knee-high lace-up boots, pairing them with a low-rise mini skirt and a barely-there bra top. This bold combination epitomized the daring and edgy fashion trends of early 2000s pop culture.
7. Lindsay Lohan’s Slouchy Ugg Boots (2004-2006)
No one rocked a slouchy, worn-in pair of Uggs quite like Lindsay Lohan in the 2000s. Whether she was running errands in LA or leaving a club, she was always spotted in a pair of Uggs—usually paired with a denim mini skirt or velour sweatpants. Love them or hate them, Uggs defined casual 2000s fashion.
8. Victoria Beckham’s Sky-High Stilettos (Even at the Airport)
Victoria Beckham didn’t believe in “casual” shoes in the 2000s. She was spotted at airports, soccer games, and even Disneyland in 5-inch stilettos. Whether it was a pair of Louboutins, Jimmy Choos, or a dangerously high Prada pump, she refused to be seen in anything but ultra-glamorous heels.
9. Jessica Simpson’s Sky-High Platform Pumps (Every Red Carpet in the Late 2000s)
Jessica Simpson was all about extra-tall platform pumps in the late 2000s, and honestly, it’s a miracle she didn’t roll an ankle. Whether she was on the red carpet or promoting her fashion empire, she never shied away from dangerously high stilettos.
Think patent leather, towering platforms, and a heel height that made walking an extreme sport. Her love for sky-high heels even influenced her own Jessica Simpson shoe line, which became a go-to for anyone wanting to channel their inner early 2000s diva.
10. Mary-Kate and Ashley Olsen’s Scruffy Ballet Flats
While the rest of Hollywood was wearing stilettos, Mary-Kate and Ashley Olsen embraced the oversized-boho aesthetic—which included ballet flats that looked a little too well-loved. Paired with massive sunglasses, Starbucks cups, and layers of draped fabrics, their distressed ballet flats were somehow chic in the most chaotic way.
11. Fergie’s Knee-High Slouch Boots (2006-2008)
Before Fergie was spelling G-L-A-M-O-R-O-U-S, she was stomping around in oversized, slouchy knee-high boots. Whether she was performing with The Black Eyed Peas or hitting a red carpet, she made sure her boots were big, loose, and folded over at the top—a true 2000s staple.
Paired with denim miniskirts, oversized belts, and chunky jewelry, these boots were the definition of “I just threw this on, but I also definitely planned this look”.
12. Mariah Carey’s Crystal-Encrusted Peep-Toe Pumps (On Every Red Carpet)
Mariah Carey in the 2000s meant one thing: sparkle. She was never without a pair of glitzy, crystal-encrusted peep-toe heels, usually paired with a bodycon dress and butterfly accessories. If it wasn’t shiny, sky-high, and borderline impractical, it wasn’t Mariah-approved.
13. Ashley Tisdale’s Over-the-Jeans Stiletto Boots (2005-2008)
Ashley Tisdale was the queen of early 2000s Disney red carpet fashion, and her boots-over-jeans era was something else. Picture this: dark-wash bootcut jeans tucked into knee-high stiletto boots, paired with a layered tank top, a cropped jacket, and at least five different accessories.
This was peak 2006 style, and while we’ve (thankfully) evolved past this trend, it will forever live on in our memories and every throwback fashion roundup.
14. Gwen Stefani’s Harajuku-Inspired Platform Sneakers (2005)
Gwen Stefani took platform sneakers to a whole new level in the mid-2000s. Inspired by Harajuku street style, she was constantly spotted in chunky, colorful platform kicks while promoting her L.A.M.B. fashion line and “Harajuku Girls” era. They were cartoonish, funky, and so uniquely her.
15. Lady Gaga’s Alexander McQueen Armadillo Boots (2009)
Lady Gaga ended the decade with the most extreme shoe moment of all time—stepping out in Alexander McQueen’s infamous Armadillo boots. These gravity-defying, 12-inch curved platforms looked more like museum pieces than actual footwear.
If anyone could make them work, it was Mother Monster herself.