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High-Fashion Looks Angelina Jolie

The Dramatic, High-Fashion Looks Angelina Jolie and More Stars Should Wear at Cannes

I am finally back from Fashion Month. I am sitting on my own couch; I slept in my own bed; and I spent the weekend catching up on TV and not thinking about fashion. With the shows and awards season behind us, I think that most of us can agree that while everyone looked good, it wasn’t the most exciting season for the red carpet. Thanks to social media and numerous best- and worst-dressed lists to deal with, no one is willing to have any fun anymore. Remember Cher’s Bob Mackie gown? She looked crazy, but it was major, and people will always remember.

Let’s continue the game of coulda, shoulda, woulda and start thinking about Cannes. Since this is my fantasy, I am also not going to worry about contracts that mean stars can only wear a certain designer, or who will actually be attending the festival. I am just going to pick five ladies I love and suggest looks from the last month of collections that won’t leave people saying, “Oh yeah, she looked pretty, right? What did she wear again?”

Angelina Jolie

I am still and will forever be Team Angie, which is not to say that I don’t love Brad Pitt as well. She is an icon, and the prettiest woman I have ever met. Yes, I have met her, and yes, that was a bit of a name drop, but it’s Angie, as I now call her. (Dear Angelina, if you are in some alternate universe reading this, I have no idea if you actually like being called Angie or Angelina, but just give me this one.) I think this off-the-shoulder sequin top with black jeans (maybe replace jeans with a slim, black tuxedo pant) from Saint Laurent would be prefect for you. Also, you won’t risk having another leg-gate.

Charlize Theron

Yeah, we’ve also met. We watched the U.S. Open together; she shared her blanket with me, and we were both screaming for Rafael Nadal to win. He did, and we were put on the Jumbotron. Afterward, I asked if she was worried about the paparazzi thinking were a couple. “Fuck ‘em,” she replied. My heart will be hers forever. In hindsight I imagine she was probably thinking, “Yeah, like people are really going to think I am dating this queen.” She always looks amazing, but plays things relatively safe, yet always sexy. I’d like to see her in this 70s-inspired mesh jumpsuit from Brandon Maxwell, which would be different for her—but still very sexy—so she would not have to stray too far from her wheelhouse.

Penélope Cruz

She is having a nice moment right now, and I have always been drawn to her. Penélope generally looks great on the red carpet, but tends to go pretty safe as well, often opting for a gown that is big and voluminous. I think it’s the Spanish in her. I know a lot of Latina women, including my own mother, and they have a flair for the dramatic. I suggest this pink pantsuit from Oscar de La Renta paired with a sequin silver cummerbund. Hair should be back, and she should wear a simple black, strappy high-heel sandal. It’s still dramatic, but less princess-y.

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