The Hills was a groundbreaking show for many reasons. Aside from giving us some top-notch drama, it gifted fans some amazing fashion inspiration. Did all of it stand the test of time? Definitely not. In the interest of preserving The Hills‘ spot in American fashion history, here are 42 memorable and slightly strange looks from this iconic show. Yes, that includes Lauren Conrad’s collection of headbands, Justin Bobby’s many hats, and more.
When Lauren Wore These Sunglasses
Sunglasses were strictly a hair accessory on this show.
When Heidi Went to School in This Outfit
Betsey Johnson everything.
Heidi’s Jeans
There’s just a lot going on here.
When Lauren Was in Her Black Headband Era
That headband was seen more than once.
When Whitney Was Forced to Wear This
Y2K fashion means tiny denim jackets.
When Audrina Wore These Confusing Pants
What style is this considered?
When Lauren Wouldn’t Stop Wearing Extra Long Tank Tops
Spaghetti strap tanks covering your belt loops were trendy back then.
When Everyone Looked Iconic at Heidi’s Birthday
This moment definitely influenced 2022’s corset resurgence.
When Heidi’s Outfit Caused Huge Drama at Work
To be fair, it’s not the most professional look.
When Heidi Wore a Tube Top Over a Tank Top
When in doubt, layer every single shirt you own.
When Lauren and Audrina Were Obsessed With Huge Sunglasses
Sunglasses should either be so tiny they don’t work, or so huge they take up most of your face, nothing in-between.
When Audrian Wore This Hat
When Justin Bobby Wore His Sunglasses Like This
How did they stay like that?
Unfortunately, This Was Very Much Not a One-Time Thing
Sunglasses have never looked stranger.
When Justin Bobby Showed Up for a Date Looking Like This
Honestly, some of these pieces would still work today.
And Showed Up at the Airport Looking Like This
It was the 2000s, after all.
When Heidi Layered Some More Tanks
When Whitney Wore This Fedora
The first of many fedora moments.
When Hilary Duff Showed Up in This Fit
Interesting fashion choices were made that day.
When Justin Bobby Layered Two Beanies
He must have sweated a lot.
When This Was Worn at Lauren’s Halloween Party
When Heidi Wore This Sweater
It’s giving Jessica Simpson in Newlyweds.
When Spencer Entered His Cowboy Phase
It was brief, but it was important.
When Lauren Wore This Cute Polka Dot Headband
When Audrina Wore Yet Another Floppy Cap
She simply couldn’t get enough of them.
When Lauren and Whiteny Wandered Around Paris Like This
She’s the girl who eventually did go to Paris.
When Stephanie Showed Up to Class Like This
When Lauren Wore a Baggy Fashion Vest
There are plenty of people out there currently wearing something similar.
When Lauren Paired a Knit Beanie with a Tank Top
It’s both a hot and cold outfit.
Let’s Not Forget This Beanie!
When Spencer Debuted His Crystal Necklace
No such thing as too many crystals dangling from one’s neck.
When Justin Bobby Wore Many Hats
When Stephanie Looked Exactly Like Season One Lauren
Definitely did a double take.
When Justin Bobby and Audrina Stepped Out Like This
Imagine running into this couple at Les Deux.
When Lauren Refused to Stop Wearing Fedoras
It was the trend that never ended.
Indoors, Outdoors…
There was simply no stopping this fedora.
When Lauren’s Pearl Necklace Was Dress-Length
That’s not a normal size for a necklace.
When Heidi Attempted Winter Fashion
Snow Heidi was everything.
When Spencer Got Into Tie Dye
When Spencer Wore This Vest to Propose
Less of a proposal and more of a “let’s get secretly married on vacation.”
When Audrina Wore This Mini Fashion Scarf
For all of The Hills ladies, nothing went better with a tank top than a scarf.
Mehera Bonner
Mehera Bonner is a celebrity and entertainment news writer who enjoys Bravo and Antiques Roadshow with equal enthusiasm, She was previously entertainment editor at Marie Claire and has covered pop culture for over a decade.
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