37. This ABSOLUTELY ICONIC Lizzie McGuire look: 36. And this iconic Raven outfit :
I hate the pirate shirt, but though the rest of the outfit is gaudy, I still love it. As you can see, I love a good monochrome moment.
Bob D'Amico/Disney General Entertainment Content via Getty Images 35. This classic Raven outfit from That's So Raven: 34. This wintery look from Raven on That's Ro Raven: Disney Channel
Honestly, out of any on this list, this is the one I'd be most likely to wear today (sans the hairpiece). The jacket and sweater are really cute. But with the hair piece and that weird feather sleeve embellishment, I felt it warranted a place on this list.
33. This classic fur coat Raven wore on That's So Raven: 32. This embellished top London wore on Suite Life:
Sadly, I can see myself having worn this in sixth grade. I can't tell if the fact that her necklace looks like part of the shirt is a good or bad thing. In the end, this is kind of tame for London, and the earrings and hair are cute.
Dean Hendler / Disney Channel / courtesy Everett Collection 31. This butterfly shirt Keely wore on Phil of the Future: Disney Channel
This is kind of cute...for a 10-year-old. It's not so wild as others on the list, so I'm ranking it low.
30. This ensemble Raven rocked for That's So Suite Life of Hannah Montana:
You know what, I don't hate the coat. It's the khaki bermuda shorts, the sequin heart tank, and the also-sequined satin V-neck top for me.
ABC Photo Archives/Disney General Entertainment Content via Getty Images 29. This rich girl look London wore on The Suite Life of Zack & Cody:
This is peak 2000s Paris Hilton vibes. The tweed, the beret, the giant hoops...another iconic, god-awful outfit.
Disney Channel 28. These retro outfits Lizzie and Miranda wore on Lizzie McGuire: 27. This dress Harper wore that literally had markers hanging off it:
Yes, this dress is ridiculous, but I felt bad ranking all of Harper's other outfits so high. This one gets an A+ for creativity.
Disney Channel 26. This layered tank top over a tie-dye shirt look with very low waist pinstripe pants Keely wore on Phil of the Future:
Every 2000s girl owned those pants, and they have got to be the worst pants in existence. Still, I don't hate the top combo.
Disney Channel / Courtesy Everett Collection 25. This strange pattern mix from Lizzie on Lizzie McGuire:
The color-block top with the orange printed pants...there's just a lot going on here.
24. This ~wild~ look from London on Suite Life:
Okay, it's VERY 2000s, and this mix of red, black, and furry leopard print is enough to land it on this list, but...I don't HATE it.
Disney Channel 23. This weird pattern mix from Lizzie on Lizzie McGuire: 22. This 3D pony shirt Lizzie wore on Lizzie McGuire: 21. This sequin headband, triangle earrings, puff fluffy jacket London wore on Suite Life: 20. This weird mix Miranda wore on Lizzie McGuire:
This would normally be a very drab outfit and would not warrant a spot on this list, but the fact that Miranda INEXPLICABLY PUT ON A CROCHET HALTER OVER HER SHIRT means I just HAD to include it. What would possess one to do this...
Disney Channel 19. This ~summery~ look from Maddy on Suite Life: Story continues
I hate this one so much because I WORE this one (or something very similar to it). I'd like to forget my past, please.
Craig Sjobin / Disney / courtesy everett collection 18. This sequin look from London on Suite Life:
Those skirts were alllll the rage in the 2000s, and I shudder to think of them again. But what really makes this outfit awful to me is the fact that London is wearing a crop top with a low waist skirt. It's more than I can bear.
Dean Hendler / Disney Channel / courtesy Everett Collection 17. Whatever's going on here with London on Suite Life: 16. This fake Lola look from Miley on Hannah Montana:
This is somehow the least bad of the Lola outfits, which I'm going to chalk up to Miley having more class than Lilly. Still, I wish she'd stuck with plaid, polka dots, OR stripes...but not all three.
Joel Warren / Disney Channel / Courtesy Everett Collection 15. This furry shoulder pad look from London on Suite Life: 14. This colorful ribbon look from Harper on Wizards of Waverly Place:
I feel like I would hate this slightly less without the jewelry and that weird sports headband.
Disney Channel 13. This layered look Lola went with on Hannah Montana: 12. This sequin lace number
Honestly, I could see the tank part maybe being cute. But that undershirt...it looks like it's from Candie's at Kohls, and it probably was. I cannot stand the fact that the undershirt has 3/4 sleeves while the sheer part has long sleeves.
Disney Channel / Courtesy: Everett Collection 11. This ~punk rock~ look Lola wore on Hannah Montana:
Every Lola outfit has five accessories too many. Someone tell me why there are TWO different belts here, and ALSO belt loops. The chunky necklace, the wrist warmers, the earrings, the layered shirts...I really cannot.
Joel Warren / Disney Channel / Courtesy: Everett Collection 10. This sequin fedora and fuchsia lycra top London wore on Suite Life: 9. Yet another layered look from Lilly/Lola on Hannah Montana:
There is just so much going on here. The cuffs, the belt, the layered necklaces, the sweater vest with a tuxedo design and bows, the belt loops...but it's got to be the bedazzled cursive L on the hip that pushes this one over the top for me.
Disney Channel/Courtesy Everett Collection 8. This graphic dress London wore on Suite Life: 7. This abomination Harper wore on Wizards of Waverly Place:
You can't see it, but her skirt is all ocean-themed too. I'd honestly think that wasn't so bad compared to Harper's other styles (it's very Mrs. Frizzle chic), but that headband ruins it for me. Tell me you love
Finding Nemo without telling me you love Finding Nemo, you know? Disney Channel 6. This ruffled camo outfit Maddy wore on Suite Life:
WHAT IS WITH DISNEY CHANNEL AND HORRIBLE CAMO SHORTS WITH A TOP THAT DOESN'T EVEN MATCH??? (You'll see what I mean when we get to #1.) Also, she's wearing an ascot. A literal colonial America ascot.
Dean Hendler / Disney Channel / courtesy Everett Collection 5. And this layered look that couldn't decide whether it was summery or wintery:
Rounding out the top five, we've got this awful concoction. The knee-high striped witch socks paired with those fluffy winter boots...then a dress with at least TWO layers underneath and all those chunky necklaces, AND the headband, and what looks to be a tie...literally everything is wrong with this outfit.
Disney Channel / Courtesy: Everett Collection 4. This duck costume Harper wore TO SCHOOL on Wizards of Waverly Place:
I don't remember, was this for a play or something??? It's Harper, so I'm gonna go with no. Also, hats aren't allowed at most schools. But that's not the biggest sin of this outfit.
Disney Channel 3. And this rubber duck outfit:
I'm ranking this above the last because it doesn't even look like it could be a costume. It's just something out of a serial killer's nightmares. Also, again with the hats, Harper?
Disney Channel 2. ANOTHER layered look from Lilly on Hannah Montana: 1. And finally, the most abhorrent of them all...this look: In conclusion... Paramount Pictures