What Would Hunter S. Thompson Wear?

Was the spirit of Hunter S. Thompson alive last night at the premiere of The Rum Diary in New York City? I'm not sure, but there sure were a lot of outfits that defied categorization, much like Thompson's writing.

What Would Hunter S. Thompson Wear?

Johnny Depp is beyond reproach. I mean, the dude's wearing tinted Woody Allen glasses, a three-piece suit, and a checkered newsboy cap. Other than Kanye, how many other modern-day dandies do we have in Hollywood? If I were Vanessa Paradis, I would have buttoned up his shirt and taken off his necklace and rings. Oh, and given his golden chains a little tug action, just because. [Ed: My nail polish matches his! Dizzy with excitement!]

What Would Hunter S. Thompson Wear?

Amber Heard is everywhere! And wherever she goes, you can bet your ass that her hair and makeup will look DIVINE. Girl gives out smoldering looks like they're free. I, on the other hand, am much stingier. (Okay, fine. I don't know how to smolder.) There's something striking about this dress, even though it's essentially a long black draped dress with a belt and an asymmetrical slit at the back. She's like a mortician babe in hot pink lipstick on her way to a party.

What Would Hunter S. Thompson Wear?

It's hard to throw your support behind a Hawaiian shirt, but I'm going to pretend Chris Benz isn't wearing one and praise him for doing the "designer goes out in wacky outfit because he doesn't give a shit!" thing. I kinda love that Zoe Kravitz is bringing back the 90's Drew Barrymore mini bangs, but that coat? Yikes. I used to have a coat like that in high school. My friend's artist mom gave it to me and I told everyone I found it in a dumpster to seem more "bohemian." Yeah.

What Would Hunter S. Thompson Wear?

It's refreshing and calming to see celebrities in weather appropriate clothing. You can be bundled up and still stylish! Just look at model Behati Prinsloo. Cute floppy hat to keep your head warm, check. Practical but stylish layers for when you move from the outdoor cold to an indoor heated space, check. Cute bag that can actually hold more than lipstick and a phone, check. As for Gina Gershon, she—like my boy Johnny—will always be a babe in my eyes. Love that necklace.

What Would Hunter S. Thompson Wear?

Would it be unfair to say that Sky Ferreira achieved what she was probably going for here, which I'm guessing is, "I spent an extravagant amount of money and time to look anti-establishment!" Model Lindsay Ellingson's leather jacket is the best one of the bunch. Ditto for that dress, which has one of the most gorgeous, interesting prints I've seen on a dress in a long time. Betsey Johnson is in her own world and her own category, which would be a category that taunts and befuddles Is it good? Bad? Ugly? It's Betsey. She defies our little games.

What Would Hunter S. Thompson Wear?

Don't get any ideas now, that's Michael Stewart's daughter. She's gorgeous, and he, unlike many who have tried valiantly before him, actually pulls off Chucks with formal wear. I swear I have seen Keith Richards' boots show up on a bunch of Midwestern fashion blogs. What else can I say about his big ass scarf, minor bling, and red headband? Never change, Keith. Patti Hansen is chic in all black. Ally Hilfiger and Steve Hash are doing that thing rich people do—making expensive clothing look slovenly. I like slovenly outfits as much as the next guy, but I hate the thought of shelling out big bucks to look that way.

What Would Hunter S. Thompson Wear?

Kiera Chaplin makes a conservative sheath dress and brown boots looks sexy as hell. The bag and skinny belt were great finishing touches. Hey, look! It's that mean girl who used to be Blair's top minion on Gossip Girl! Mustard yellow looks fabulous on Amanda Setton, but why the vest and why that super tight mini skirt? If you're ever in a pinch for a chic outfit, take some cues from Dree Hemingway. Pair a tailored jacket in a vibrant color with a well-cut t-shirt and jeans, then add a pair of ballet flats and you are good to go.