How to Dress Like a Woody Allen Heroine

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He's given the actresses of our century some brilliant female roles, and he's never afraid to let women capture the audience's attention. His latest film, Blue Jasmine, follows the time-honored Allen tradition of letting the female lead quip, stumble, and shine. He's also mastered the art of characters that appear realistic and sexual at the same time; his heroines don't need to be perfectly made up to get what they want. The formula for dressing like a Woody Allen heroine is never going to be as simple as "pair a bright red lip with a classic up-do." The rules are a little more conceptual than what you're used to—and that's exactly what makes these girls so great. 

Woody Allen, Ahem, Loves Women

He's given the actresses of our century some brilliant female roles, and he's never afraid to let women capture the audience's attention. His latest film, Blue Jasmine, follows the time-honored Allen tradition of letting the female lead quip, stumble, and shine. He's also mastered the art of characters that appear realistic and sexual at the same time; his heroines don't need to be perfectly made up to get what they want. The formula for dressing like a Woody Allen heroine is never going to be as simple as "pair a bright red lip with a classic up-do." The rules are a little more conceptual than what you're used to—and that's exactly what makes these girls so great. 

Let your makeup reflect your mood

Don't treat makeup as a mask that you present to the world — treat it as an extension of your moody, messy self. One of the most memorable parts of Vicky Cristina Barcelona was Penelope Cruz' smudgy black eyeliner, the perfect reflection of her volatile personality.

Do not stress about your hair. Repeat: do not stress about your hair.

A Woody Allen heroine wouldn't be herself without hair that's tossed into a ponytail, falling around her face in slightly sweaty strands, or nonchalantly messy due to sudden thunderstorms/Spanish love affairs/existential crises. Show me a Woody Allen character with perfectly done hair and I'll show you that you're watching the wrong movie.

It's perfectly fine to dress realistically

The world of fashion is aspirational, and that's part of its charm. But you can't spend all day in Louboutins and bandage dresses — sometimes a girl just needs to wear a t-shirt and jeans. Thankfully, Allen is never afraid of showing us just how charming a casual wardrobe can be.

And it's especially fine to be your strange self

Two words: Annie Hall. Wait, ten words: Diane Keaton in every one of her Woody Allen roles.

You don't have to show skin

Woody Allen really doesn't get enough credit for his female characters' costumes. Sometimes they err on the side of bland, but unless they're playing a prostitute, his characters rarely resort to blatant sexual display in order to demonstrate their allure. It's not uncommon to see them on dates in button-downs and jeans, or wandering foreign cities in practical shoes. Their outfits often seem to stem from a sort of internal motivation — "This feels comfortable," or "I like the way this looks"— rather than external pressure to look desirable.

Be the better woman

Allen's leading ladies are always hotter than he is. We're talking ten times hotter, minimum. But they're never ice-cold arm candy designed to be seen and not heard — they're opinionated weirdos with their own psychoses, hobbies, and dreams. They may be flawed, but they're usually trying to better themselves in some way. They don't always succeed (cough, Vicky) but effort is half the battle. The other half is a really great script.