KIERNAN SHIPKA in Los Angeles // dress by Oscar de la Renta, purse by Proenza Schouler, shoes by Miu Miu
I could live a hundred fifty years, and make enough money to buy all the most fabulous things on earth, and still never be as stylish as Sally Motherfucking Draper. I wish I were exaggerating, but LOOK at her. Look at that perfect dress (the pockets! I die!), her adorable accessories, her refreshing “I’m twelve years old and I don’t need to cover my face in makeup or over-style my hair because I am naturally ridiculously beautiful” attitude. But when I wikipedia-ed her to double-check her age, and realized she was born in 1999, I almost threw up in my mouth. Am I really old enough to be twice the age of someone this stylish?
ANNE HATHAWAY in New York City // purse by Christopher Kane
So beyond over the nude shoes, but the purse is adorable and the dress is killer. I am all about that fabulous print, Annie!
VIOLA DAVIS in New York City // dress by Rachel Roy, shoes by Brian Atwood
I’m not a huge fan of the fringe happening around her ankles, but holy crap is this dress perfect on her. Color, silhouette, fit – Viola has never looked better.
JESSICA BIEL in New York City // dress by Oscar de la Renta, shoes by Louis Vuitton
I think this is the only time I’ve ever looked at Jessica Biel and thought, “Yup, that style suits her.” She always looks a touch out of place in whatever she’s wearing (I think because she’s not a particularly stylish person in general), but she actually looks right at home in this fab little Oscar dress.
JESSICA BIEL in New York City // dress by Giambattista Valli, purse by Fendi, shoes by Casadei
Then she reverts back to look-at-me sex appeal, and I just can’t buy it. Not because she’s not sexy – she’s obviously gorgeous. It’s just this fuck-me-pumps-and-animal-print thing feels really contrived on her. Maybe it’s because no one pairs a leopard-print dress and fuck-me pumps with a giant tote bag, though.
EMMY ROSSUM in New York City // dress by Monique Lhuillier
I hate the makeup so much it hurts – blue eyeshadow and bubblegum pink lips? WHAT CENTURY IS THIS?! – but that dress is purrrrfect on her. She’s positively itsy-bitsy in it, and the color is fabulous, but she seriously needs a stylist who can clean up the details for her.
SOPHIA BUSH in Los Angeles // blazer by IRO, purse by Chanel, shoes by Christian Louboutin
I’d love the look, but that straight-from-the-gym tank and visible black bra underneath are killing me. I’m not opposed to a visible bra, but when it’s black and popping out of a crappy white shirt, you can’t not think “trailer-trash hooker,” am I right? Regardless, the jacket and leather pants combo is actually killer, and the accessories are simple but very stylish.
KEIRA KNIGHTLEY and JAMES RIGHTON in New York City // dress by Erdem, purse by Chanel, shoes by Tapeet
It’s not enough to be walking through the streets of Manhattan looking divinely happy with an adorable and equally blissful man, is it, Keira? You have to wear the perfect little Erdem sundress and effortlessly chic accessories too? We get it. You have it all. Congratu-fucking-lations.
JOSHUA JACKSON and DIANE KRUGER in Los Angeles // top and jeans by Current/Elliott, shoes by Bally
I think I wore this outfit to Gymboree when I was four, but I can promise you, my pink jeans and gray animal print tee were not nearly as expensive as Diane’s. But I’m sure I looked equally as fabulous as she does here.
MICHELLE WILLIAMS in Hollywood // top by A.P.C., shorts by Joie, sunglasses by Ray-Ban, shoes by Ancient Greek
I need a word for hipster-starlets (hipstarlets? manic pixie dream stars?), because Michelle Williams is displaying some killer hipster-starlet street style here. Mixed prints, Ray-Bans, perfect hair, delicious European-looking sandals, and a coy smile and wave for the paparazzi. Bitch knows how it’s done.
DIANNA AGRON in Paris // sunglasses by Dolce & Gabbana, shoes by Miu Miu
This dress is embarrassing on anyone over the age of ten, and seersucker isn’t something I’m a fan of in general. But her accessories are so cute, I almost don’t care. Almost.
SAMI GAYLE in New York City // top, skirt, and shoes by Miu Miu
Sixteen-year-old Sami Hayle is the next actress whose name you need to learn, since she’ll be in some big movies in the next few years. I immediately recognized her name, and not just because I also grew up with the nickname Sami, spelled the same way, which is less common than you’d think. But when I saw Patti LuPone in Gypsy at Lincoln Center a few years ago (just before it got moved to Broadway), a darling little thing named Sami Gayle played Baby June – brilliantly, I might add. So you go, little baby Broadway powerhouse, growing up and hitting the big screen and wearing Miu Miu! You’re making the Democracy Diva so proud.
LIZZY CAPLAN in Locarno, Switzerland // dress by Lisa Ho, shoes by BCBG
Despite her awful taste in shoes, Lizzy Caplan is pretty darn awesome. If you vaguely recognize her, it’s probably because she played the unsinkable Janis Ian in Mean Girls. Her dress is cute, but the individual prints themselves aren’t particularly pretty. But I love the wavy bob and I’m looking forward to seeing her tear up the red carpet, just as soon as she changes her shoes.
JENNIFER GARNER in Los Angeles // dress and shoes by Lanvin
When did Jennifer Garner become the most boring woman on the red carpet?
NICOLE KIDMAN in London // dress by Azzedine Alaïa, shoes by Manolo Blahnik
Oh, Nicole. Aren’t you a little grown up for this? Haven’t you seen enough of this world to know that black spiderweb booties will make any woman look like a stripper?
RASHIDA JONES in New York City // dress by Thakoon, shoes by Valentino
Cute dress, but she’s always got an awkwardly placed belt and a pair of shoes that don’t match. Rashida, you’re so lovely, and you at least gravitate towards interesting things. Please, let me style you. Please.
RASHIDA JONES in Los Angeles // dress and blazer by Boy. by Band of Outsiders
No, seriously, Rashida. A stylist. You need one. Stat.
MAGGIE GYLLENHAAL in New York City // jumpsuit by Zero + Maria Cornejo, blazer by Moschino Cheap & Chic
This is making me sad. I can’t look at an elastic waistband on the red carpet and not get at least a little bit depressed. I really just don’t understand what Maggie Gyllenhaal sees when she looks in the mirror. An old woman? A 1970s lesbian?
ASHLEY GREENE in Hollywood // dress by Yigal Azrouël, shoes by Barbara Bui
I swear, she’s getting more boring by the minute. And wearing more and more makeup every day, apparently. I think she’s doing this specifically to annoy me.
ANNA KENDRICK in Los Angeles // dress by Mulberry, purse by Edie Parker, shoes by Hervé Léger
Any woman old enough to menstruate should be embarrassed to be seen in this outfit.