“Homeboy Wore Combat Boots to the Beach”: The Best Fashion Moments From The Hills

Some trends die, but truth and time tells all.

2006 MTV Movie Awards - Arrivals
Photo by Steve Granitz/WireImage

Tonight, The Hills–the defining cultural artifact of the mid-2000s–is finally returning to television, with a new season titled The Hills: New Beginnings. The aughts are trendy again! In case you forgot, or are too young to have ever watched in the first place, The Hills was a show that introduced legions of teen girls to the workings of the fashion industry via our omnipresent narrator Lauren “LC” Conrad. It wasn’t exactly realistic (in what universe do interns get to go to Paris for fashion week?), but the series’s Teen Vogue-adjacent setting inspired thousands of internship applications and turned its stars into fashion icons. The show is synonymous with so many of the era’s major trends: bubble dresses, going out tops, low-rise jeans, bug-eyed sunglasses, pre-Blair Waldorf headbands, enormous waist belts, etc. And so, in honor of the show’s revival, we’re taking a look back at a few of its most iconic fashion moments—and to be honest, a decade later, they still kind of hold up! To quote the sage-like Justin Bobby, “truth and time tells all.”

Lauren Conrad Flat-Ironing Her Outfit

On the pilot of The Hills, Lauren Conrad was told to come to Teen Vogue for an interview hours before it was scheduled. As she rushed to get ready, she made an inspired choice ages before Buzzfeed would call it a lifehack: she flat-ironed her outfit to get rid of wrinkles. It matches her pin-straight hair! Ah, 2005.

Lauren Conrad flat-ironing a dress.

LC and Whitney’s First Day at Teen Vogue

In the pilot episode, LC and Whitney Port embarked on their intern journey together at Teen Vogue’s Los Angeles office. They nervously looked each other up and down before forming a lasting bond in their fake closet office. And there was a lot to look at! Both sported looks that seem straight from Robinson Boulevard, outfits wholly emblematic of the era. Whitney wore a pink eyelet baby doll dress with an enormous brown belt at the waist, pairing it with a giant brown leather satchel. And Lauren’s outfit was so 2005 it hurts: white bootcut jeans with a beige going-out-top dripping with sequin paillettes.

Whitney Port’s first day at “Teen Vogue.”

Whitney Port and Lauren Conrad on “The Hills.”

The Dress LC Ruined in Paris

Lauren Conrad may forever be known as “the girl who didn’t go to Paris,” but she did eventually make it to City of Lights. When in town with Whitney to work on the Crillon Ball, an event for international debutants, Lauren was whisked away by a French hottie on a motorcycle (Conrad eventually admitted that the interaction was totally staged and that she didn’t even like the guy). LC and Whitney were loaned Alberta Ferretti gowns for the occasion, and Lauren managed to ruin hers with an errant curling iron. Whitney, as per usual, saved the day by managing to convince the Ferretti store manager to cough up another gown.

The Dress Whitney Tripped Over on Good Morning America

In another totally normal, average intern activity, Whitney appeared on Good Morning America for a segment celebrating famed dresses worn to the Academy Awards. Whitney was given Hilary Swank’s backless Guy Laroche gown from the 2005 ceremony. And she tripped over it! A very rare screw-up.

Heidi and LC’s New Year’s Eve Outfits

Heidi and LC rung in 2006 in an epically disastrous way (lots of tears). But they looked so innocent while getting ready for the evening! Look at Lauren’s huge curls and Heidi’s era-appropriate chihuahua.

Heidi Montag and Lauren Conrad in “The Hills.”

LC’s Headbands

LC wore so many headbands over the course of the run of the show: hard headbands, soft headbands, braided headbands, headscarves, gilded headbands, headbands that stood stiff and strong against huge bump-its. Eat your heart out, Gossip Girl.

Lauren Conrad in “The Hills.”

Justin Bobby’s Combat Boots at the Beach

Homeboy wore combat boots to the beach. He really did! Though it wasn’t his fault: in an interview years later, Justin Bobby Brescia explained why he wore such sweaty footwear to an outing by the sea. “Me showing up in combat boots and stuff to the beach is just because they called me on my off day and asked me to actually shoot some scenes and I was with my boys riding Harleys,” he told Us Weekly. He also maintained that a scene where he abandoned Audrina at a beach house without a ride home was totally staged. It still made for excellent television.

Spencer Pratt’s Tie-Dye and Crystals

When this episode aired, fans had thought the long-villainized but vaguely sane Spencer had officially lost his marbles. But retrospectively, the man was so ahead of the curve! Crystals are so trendy now. And the tie-dye! Spencer Pratt is a genius.

The Blue Dresses

The mid-season finale on season five of The Hills was epic. Spencer and Heidi finally had the televised wedding of their dreams, and Lauren Conrad exited the show. LC showed up to make good with Heidi, clad in a blue dress. She makes up with her former friend, wishes her the best, and leaves. Enter her replacement, Kristin Cavallari, who producers clad in a dress in the exact same shade of blue. Visual poetry.

Lauren Conrad on “The Hills.”

Kristin Cavallari on “The Hills.”