I’m obsessed with the 1999 teen drama movie ‘Cruel Intentions’ just as much as anyone else is. (I’m going to give you a summary of the movie)

The incestuous relationship between socialite coke-head bitch Kathryn (Sarah Michelle Gellar) Merteuil and Sebastian (Ryan Phillippe), the sexual innuendos, the I’m going to screw you to get what I want and I don’t care scenarios, the twisted, sadistic scheming all tied around one BET and a journal.

The journal is written by Sebastian and chronicles every scheme Kathryn had done, her secret drug use and the BET.

Sebastian must bed the little miss plain-Jane Virgin Annette Hargrove (Reese Witherspoon), the daughter of their prep school’s new headmaster who according to Kathryn  is a “paradigm of chastity and virtue”. If Kathryn wins, she gets Sebastian’s Vintage Jaguar XK140, the infamous car that he drives in throughout the movie. If Sebastian wins, he gets to have sex with Kathryn.There’s another part of the bet that involves Kathryn trying to befriend Cecile who falls in love with her music teacher and tries to break the relationship up because her EX-boyfriend left her for Cecile, so it all makes sense in a way, this is her REVENGE

Surprisingly he ends up losing the bet after falling deeply and passionately in love with Annette. Sebastian always thought he was incapable of loving any woman, or feeling any type of love for that matter. Love terrified him, but in a good way. As Sebastain and Annette start their relationship, Kathryn grows increasingly jealous ultimately driving her insane, she plans her revenge.

She starts by manipulating Sebastian into breaking up with Annette by threatening to tell Annette’s father all about his bad-boy past.

And he breaks up with her just like that all because Kathryn couldn’t have her way and wanted Sebastian all to herself.

Kathryn tells him:  “You were very much in love with her. And you’re still in love with her. But it amused me to make you ashamed of it. You gave up on the first person you ever loved because I threatened your reputation. Don’t you get it? You’re just a toy, Sebastian. A little toy I like to play with. And now you’ve completely blown it with her. I think it’s the saddest thing I’ve ever heard.” After taking a sip of her champagne she ends the conversation with, “So I assume you’ve come here to make arrangements, but unfortunately, I don’t fuck losers.”

Kathryn then tells Cecile’s music teacher that Sebastian had hit her (which is totally not true) and engaged in oral sex with Cecile (yeah that is totally true).

The music teacher is obviously enraged with anger, so the next day when Sebastian goes to see Annette to apologize and get her back, the music teacher spots him and then punches him in the face, beating him to the ground. Annette sees the fight and runs over to stop it, the teacher accidentally pushes her away and she is lying on the ground in front of on-going traffic, a car comes, Sebastian rescues her by using his body as a shield,  ‘pushing her to safety’ and is hit by the car. Bruised and bloodied to no end, lying on the ground, while Annette comforts him, he confesses his love for her and then tragically dies.

A huge funeral is held at the school for Sebastian, where Kathryn attends and gives a speech about her step-brother in which she lies telling them that she loved her brother, blah blah  peer pressure blah blah lies.

Before the funeral she has an encounter with Sebastian’s lady love Annette, where she (Annette) puts on a little act, trying to make it seem like she knows nothing to basically trick Kathryn.

Unbeknownst to her, Annette has made Sebastian’s journal into a book and gives it to all the students at the school including Cecile. Kathryn gets super super pissed and yells “what is happening, don’t you have any respect!” at the other students because they are leaving the funeral.

She runs out and Cecile gives her Sebastian’s book called CRUEL INTENTIONS.She reads it. looks up at everyone shaking their heads at her in disgust.

Her father and mother had read it as well, he grabs the cross she wears around her neck during the movie, which has her coke in it.

He shakes his head. Kathryn is now the unpopular bitch who has no friends, and is no longer the school’s president.

At the end of the movie Annette rides off into the sunset in Sebastian’s beloved Jaguar with his journal at her side.

He basically died for her and it is truly a brilliant ending I must say. And the fashion is even more brilliant than the movie.

The vintage, school-girl-y type style is what attracted me to the movie the most. I was wearing those type of outfits during my days in elementary school, the frilly dresses, the short mini skirts.

Also Kathryn’s dark and sometimes intense makeup gave me major #MakeupGoals But that infamous scene where she’s teaching Cecile how to kiss a guy while dressed up in a black sexy emo “I’m going to a funeral” suit with a floppy hat to match. There’s a sort of  darkness to her wardrobe that I absolutely love.

The Cruel Intentions costume designer  Denise Wingate talked with ‘Dazed Digital’ 6 months ago about the hidden meaning behind Kathryn’s sexed up style.

She said: “I tried to blend high-end fashion with a mix of pieces I designed and made that were a nod to the original film, for example using this corset and ruched bustier with a Dolce & Gabbana suit on Sarah Michelle Gellar.”

She also tried to match Sebastian’s wardrobe with his ‘rich boy persona’ along with Annette’s innocent virgin school-girl look.

Ryan aka Sebastian wore tons and tons of PRADA, which was quite the hot commodity within the fashion industry and worn by many celebrities. Denise said, “I used a lot of Prada on him which was very hot at the time. I made a long coat for Ryan that was taken from a pattern from an 1800s men’s frock coat and lined it with bright fuchsia silk to make it look more contemporary.”

And the girl next door Reese Witherspoon (Annette) who was actually Ryan Phillipe’s girlfriend in real-life at the time was a lot more modest than the other two. “Her palette was softer and sweeter but confident. Believe it or not those high-waisted pants were in fashion then. I remember we wanted her in all white in contrast to Ryan’s all black, and when he gets hit by a car and sees her it’s almost as if she is an angel.”

Kathryn and Annette were my favorite characters in the movie. Sarah and Reese are both very talented actresses, and most of all are totally stylish.

I have always loved this movie, I think I was about maybe 13 years old when I first watched it. Obviously I couldn’t watch it at 9 or 10 years old, it was super inappropriate and way too sexual for me so I waited a couple of years to actually see it on TV.

Cruel Intentions made my whole teen years that much more amazing (besides mean girls and gossip girl) learning about the dangers of sex and that love can make you do crazy things, was the icing on the cake. I mean I knew about sex and all those things before, but I wasn’t given a real lesson on it and what could happen, the consequences, etc.

It opened my eyes and definitely kept me informed. It was interesting and entertaining. (and I watched it last night on VH1).

So I thank you Cruel Intentions for teaching me what every girl has to and needs to know.

Oh and I want to thank Sarah and Reese for being my style muse and also giving me ultimate #FashionGoals every damn time I watch it.

You can read the interview between Dazed Digital’s Alexandra Hayward and the Cruel Intentions costume designer here: http://www.dazeddigital.com/fashion/article/28403/1/the-hidden-meanings-behind-the-clothes-in-cruel-intentions

Now let’s take a look back at all the stylish moments and infamous quotes from the movie.


He never loved you Kathryn, #SorryNotSorry

This look is everything.

YAS Sarah is doing the new #CruelIntentions TV show revival. #OMG #Flashback #Throwback

YUP. She’s right Sebastian.


This look is everything. #perfection #style #fashion #CruelIntentions #SarahMichelleGellar

LOL Sebastian.

-says the mother

-says the music teacher #LOL #SoFunny

You wish.

Here is the beautiful infamous love scene between Annette and Sebastian with the song ‘Color Blind’ by the Counting Crows.

#couple #cruelintentions #lovemakingscene

Wow! the cast looks so different back then (but still good-looking now!) and the movie actually was originally going to be called ‘Cruel Inventions’ which Sarah revealed on her Instagram.

This scene though.

Kathryn trying on that purple flower-y vintage dress

'Best girls night of the year!' The actresses were thrilled to be together again

‘We’re Reunited’ photo courtesy of DailyMail.co.uk and Reese Witherspoon! #Reunion #CruelIntentions

That scene.

Those glasses and that suit.

The Jaguar.

the school girl outfits. The photos are courtesy of the Vogue Australia website:http://www.vogue.com.au/miss+vogue/news/galleries/how+cruel+intentions+defined+late+90s+fashion,31519 (just want to give credit where it’s due!)


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