Skip to main content
Woman struggling with hair loss, looking concerned.
Woman enjoying a donut at night, cozy setting.
Bianca Censori showcasing fall/winter fashion collection.

Celebrity

10 Outfits Celebs Actually Wore 10 Years Ago That Will Make You Cringe Today

July 5, 2016 by Caroline Pirozzolo
shefinds | Celebrity
Featured image

Here's a fun way to feel really old: 2006 is already 10 years behind us. As in, 10 years ago, Miley Cyrus was still Hannah Montana, Kim Kardashian was still BFFs with Paris Hilton, and iconic boutiques Kitson and Scoop were alive and well (RIP). Wow, that was fast. It turns out our fashion tastes have changed a little (read: a lot), too. Click through to see what our favorite celebs were wearing 10 years ago. You won't believe how much has changed!

[Photo: Westley Hargrave/Splash News]
Elegant bridal hairstyle inspiration for weddings and special events.

Kim Kardashian

Right around the release of her infamous sex tape, Kim Kardashian stepped out in a metallic dress with a slouchy hobo bag - oh, and a chunky, early '00s digital camera. (For selfies, obviously.)

[Photo: Splash News/Titomedia.com]

Sunscreen product for flawless skin protection during summer.

Heidi Klum

Considering Heidi Klum's look here and about three of Anne Hathaway's outfits in The Devil Wears Prada (which also turns 10 this year!) it's clear newsboy caps had reached their peak in '06. *Shudders*

[Photo: Ronald Asadorian/Splash News]

Stylish kids' fashion for casual and special occasions.

Jessica Simpson

2006 had everyone (including Jessica Simpson, apparently) hoarding cropped jackets.

[Photo: Doug Meszler/Splash News]

Trendy outfit ideas for a chic lifestyle look.

Jennifer Aniston

Because who could forget the bootcut jeans tucked into knee-high boots look?

[Photo: Splash News/Canham/Whittle]

Beautiful makeup looks for glamorous events and parties.

Paris Hilton

Pink Juicy Couture tracksuit + oversize sunglasses + hobo bag. Oh, and Paris Hilton heading into Fred Segal in LA. Need we say more?

[Photo: London Entertainment/Splash News]

Contemporary fashion pieces for modern women.

Lauren Conrad

In the midst of her Laguna Beach days, Lauren Conrad arrived at fashion week in a boho-esque belted dress and massive sunglasses because, obviously.
[Photo: Aaron St. Clair/Splash News]

Romantic wedding bouquet arrangements for brides.

Lindsay Lohan

2006 was a weird year for our jeans, which were in the process of transitioning from bootcut to skinny, resulting in some interesting baggy shapes.

[Photo: Ronald Asadorian/Splash News]

Classy evening attire for formal gatherings and events.

Halle Berry

2006: a.k.a. the year when Uggs were actually worn with outfits that weren't pajamas.

[Photo: Ronald Asadorian/Splash News]

Fresh beauty products for everyday skincare routines.

Kate Moss

In 2006, the piled-on boho look (as pioneered by MaryKate Olsen) was everything, as Kate Moss's look here proves.
[Photo: Splash News/Mirrorpix]

Fashion accessories to elevate any outfit choice.

Sarah Jessica Parker

A polka dot dress with a belt that cinched it at the waist? Sounds about right.

[Photo: Jackson Lee/Splash News]

Queen Camilla and Kate Middleton attending a royal function.
Kim Kardashian at the Kering's 3rd Annual Caring for Women Dinner.
Kylie Jenner and Stormi Aire with Timothée Chalamet at an event.
Madonna at the Met Gala in a stunning outfit.
Taylor Swift arriving in a private jet in 2024.
Jennifer Lopez in Defaience at the 2025 American Music Awards.
Vittoria Ceretti with Leonardo DiCaprio at a gala.
Emma Stone attending the Annual Actor Awards ceremony.
Salma Hayek at the 12th Annual Breakthrough Prize Ceremony.
Kate Middleton during a state visit looking elegant.
Ariana Grande showcasing her fashion at the Golden Globes.
Kylie Jenner's elegant ensemble at the Met Gala 2025.
Taylor Swift and Travis Kelce enjoying a night out.
Ivanka Trump and Jared Kushner attending a public event.
Brad Pitt and Ines De Ramon at the European premiere.
Bad Bunny's glamorous Grammy moment, celebrating music and style.
Angelina Jolie celebrating at the Trophee Chopard Award ceremony.
Selena Gomez supporting mental health at Rare Impact Benefit.
Brad Pitt and Ines De Ramon at the F1 premiere event.
Queen Camilla with Prince Harry and Meghan Markle at an event.
Queen Camilla and Kate Middleton attending a royal function.
Kim Kardashian at the Kering's 3rd Annual Caring for Women Dinner.
Kylie Jenner and Stormi Aire with Timothée Chalamet at an event.
Madonna at the Met Gala in a stunning outfit.
Taylor Swift arriving in a private jet in 2024.
Jennifer Lopez in Defaience at the 2025 American Music Awards.
Vittoria Ceretti with Leonardo DiCaprio at a gala.
Emma Stone attending the Annual Actor Awards ceremony.
Salma Hayek at the 12th Annual Breakthrough Prize Ceremony.
Kate Middleton during a state visit looking elegant.
Ariana Grande showcasing her fashion at the Golden Globes.
Kylie Jenner's elegant ensemble at the Met Gala 2025.
Taylor Swift and Travis Kelce enjoying a night out.
Ivanka Trump and Jared Kushner attending a public event.
Brad Pitt and Ines De Ramon at the European premiere.
Bad Bunny's glamorous Grammy moment, celebrating music and style.
Angelina Jolie celebrating at the Trophee Chopard Award ceremony.
Selena Gomez supporting mental health at Rare Impact Benefit.
Brad Pitt and Ines De Ramon at the F1 premiere event.
Queen Camilla with Prince Harry and Meghan Markle at an event.