Skip Nav
Award Season
See Every Gorgeous Arrival at the NAACP Image Awards
Spring Fashion
The 8 Spring Shoe Trends You'll Be Wearing All Season
Fashion Week
Our New App Will Give You VIP Access to Everything NYFW

Back to Cool: Cruel Intentions

School is almost in session — cue bells — and my assignment is to help you look smashing on your first day and beyond. First up for inspiration, the naughty naughty Cruel Intentions. This 1999 flick will forever be etched in my memory because of its scandals, girl-on-girl action, and almost-incestuous love scenes. I'm not advocating that kind of behavior, but I am advocating the sexy chic style of Sarah Michelle Gellar's character Kathryn and the preppy cute look of Reese Witherspoon's Annette.

Around The Web
Fashion Says You'll Be Wearing Sweater Vests This Spring
The Key to Freddie Prinze Jr. and Sarah Michelle Gellar's 13-Year Marriage
Reese Witherspoon Draper James Bag
How to Dress Like Amal Clooney
Sarah Michelle Gellar at Swiffer Event 2016
Cruel Intentions Cast Reunion
Sexiest Dresses at the Golden Globes 2016

POPSUGAR, the #1 independent media and technology company for women. Where more than 75 million women go for original, inspirational content that feeds their passions and interests.

Join The Conversation
BellaEdward4ever BellaEdward4ever 6 years
phillippe* oops and also, although kathryn was totally evil, she had a great wardrobe.
BellaEdward4ever BellaEdward4ever 6 years
I saw this post and decided to buy the movie on itunes and watch it, and I loved it (btw I'm fourteen). wow....ryan phillipe is ridiculously hot.
sham28 sham28 6 years
HAHA I have it on VHS somewhere!
bellanatella bellanatella 6 years
Florida-Snow Florida-Snow 6 years
Oh god how I love this movie. Such a guilty pleasure...
runningesq runningesq 6 years
that Riva yellow flat is adorable ! want want want
genesisrocks genesisrocks 6 years
Love the fashion. SMG's clothes work for today
pattybaby pattybaby 6 years
awwh kwl post!! I loved this movie :)
Talldiva45 Talldiva45 6 years
I used to love this movie - think Ii have it on DVD somewhere. The fashion is pretty cool too.
onlysourcherry onlysourcherry 6 years
loved this movie in high school. The dialogue is so cheesy now but the fashion isn't.
Latest Fashion