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The year was 2001, your bootcut jeans were ripped at the back from how often you accidentally stepped on them, and you’d just figured out how to burn mixed CDs. If put on the spot, you could 100 percent hit all the harmonies from “Lady Marmalade.” Your favorite movie? Legally Blonde with a side of A Knight’s Tale. Your style icon? Hilary Duff with a side of any given model from your Delia*s catalogue.
And speaking of Hils, I’m gonna go ahead and assume you’ve forgotten about some of her more bold—and some might say iconic—fashion choices. Perhaps intentionally. But we’re here to remind you of all the Hilary style moments you were fully obsessed with back in middle school / high school / elementary school (not sure how old you are, so just go with me here)—from her platform flip-flops, to her aesthetic scarfs that served no functional purpose, to a truly bold number of cropped pants.
What I’m saying here is that every item of clothing that Hilary’s ever stepped into has looked incredible, and frankly I’d still wear about half the outfits in this gallery. Okay, less than half. Maybe a quarter. Anyway, if you don’t come away from these throwback pics reaching for the nearest available pair of bootcut jeans and making your mom dig through the garage to mail you what’s left of your early aughts wardrobe, I won’t even know what to think, bye!
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This Useless Piece of Fabric Masquerading as a Cardigan
*immediately purchases a used shrug on eBay*
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The Rise on These Jeans
The length of this fly is a personal attack against me.
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This Scarf
Hello and welcome to Hilary’s Scarf Era.™
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And This Scarf
Anyone know who knitted this? I just wanna talk.
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And Frankly Also This Scarf
I know what you’re thinking: surely this is a choker? No. You’re wrong. It’s a scarf. It’s never not a scarf.
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These Von Dutch Pants
Straight bangs ✅curled hair ✅Von Dutch pants ✅
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This Double Layered Tank Top
Why stop at one cotton tank top when you can wear two cotton tank tops over each other? Extra points if they match your clip-in hair streaks.
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And This Layered Tank
Is a tank top even a tank top if it’s not being layered? Do we need air to breathe? Both rhetorical questions.
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These Platform Snowboots
If you weren’t wearing these with a pair of leggings and calling it an outfit, I don’t know what you were doing!
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These Pinstripe Pants
Who else begged their mom to take them to Hot Topic for pinstripe pants? We’ll get through this trauma together!
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These Teeny-Tiny Spaghetti Straps
The thinner the straps, the closer to god.
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This Poncho
If wearing a chunky knitted poncho to the 2005 “DVD Exclusive Awards” is wrong, I DON’T WANT TO BE RIGHT.
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These Chunky Beaded Necklaces
10/10 convinced my mother bought me these at our local Talbots in 2005.
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These Strappy Sandles
Everything about this look is perfect and timeless and I won’t hear otherwise!
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This Dress Over Pants Moment
Why commit to pants or a dress when you could just wear both?
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These Platform Flip-Flops
The see-through jelly tops!!!! I’m unwell!!!
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This Emo Newsboy Hat
Travis and Kourtney are shaking.
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This Entiiiiiiiire Look
The turtleneck. The aggressively ripped bootcut jeans. The rise on those aggressively ripped bootcut jeans. The duffle purse. The frosted eye shadow. JUST ALL OF IT.
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This Red Carpet Moment
Hilary’s green dress at the Cheaper by the Dozen 2 premiere walked so J.Lo’s green dress at the Grammy Awards could run.
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This Chain Belt
Please note that it’s going through 0/10 of the loops.
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And This Chain
If you didn’t have a wallet on you, you could always attach your wallet chain to your belt loops.
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This Oversized Shirt
When it doubt, steal a shirt from your dad’s closet, uselessly belt it, throw on some leggings, and call it a day.
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This Whole Vibe
When you have to deliver newspapers in 1940 at noon and have P.Diddy’s White Party at 10 p.m.
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This Hervé Léger
If you didn’t wear a Hervé Léger in 2009, you were not a real celeb.
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This Chunky Belt
Much like its friend a few slides ago, this belt is putting absolutely no work into holding up Hilary’s pants.
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These Burnt Velvet Flares
Honestly would wear today.
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Whatever…This Is
Me looking at these shoes.
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These Uggs
No pair of Uggs is complete without a matching small dog in a bag.
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This Floor-Length Cardigan
For when your shrug isn’t cutting it.
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THIS ICONIC MOMENT
I can literally hear this photo.
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Mehera Bonner is a news writer who focuses on celebrities and royals.
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