How to Dress Like Your Hipster Idols

When I was a little girl, if I liked something a lot, I typically tried to emulate it.

Take for instance the time I burned a cork and drew giant Jewish eyebrows on myself to transform into Rod Serling. Or the other time I burned a cork and drew giant Jewish eyebrows on myself to look like Groucho Marx. Or the time I burned a cork and drew giant Greek/Italian/Arab eyebrows on myself to look like Frank Zappa.

Hm.

Looking back at that paragraph just explained a lot.

I truly believe that certain movies and characters have defined who I am today. Annie Hall told me it was ok to dress like a boy. Pee-Wee showed me the advantages of bow-ties. George McFly and Egon Spengler proved that nerdy could be sexy. Andie Walsh explained to me that buying second-hand can look classy. Sloane Peterson told me that fringe jackets and shorts kind of go together?

If you're anything like me, then you like to honor your hipster "young, creative urbanite" Gods. Below are some of my favorite hipster "young, creative urbanite" movies and their stylish lead characters.

1.) Annie Hall- The ultimate fashion icon. Diane Keaton made dressing like a boy sexy. What really makes her so attractive though? The comfort and confidence she has in her own skin...and that is not for sale.

For Annie Hall, buy a men's dress shirt at any thrift store (there is never a shortage of them). The slacks and vest will be a little more tricky. I don't recommend buying men's pants or vest. It will be too big. As you can see from the picture above, her pants/vest still fit her body appropriately. If you like knowing that small, bleeding hands made your clothing, then try the Top Notched Vest at Forever 21. For the hat, check out American Apparel's Floppy Hat (but don't buy the one at the South Congress store, it's MINE!) As for Alvy Singer's outfit, all you need is a whole lotta noodginess.

2.) Heathers- Nothing says classy like croquet and bulimia, right Heather? Finding shoulder-padded jackets should not be hard. People are more than happy to get rid of their horrible fashion decisions from 20 years ago. And for whatever reason skorts are back in style, so sadly, you shouldn't have any trouble finding some of those. Or try the Reformed Kelly Skort at Urban Outfitters. For fun opaque pantyhose, check out American Apparel's crazy-ass line. Make sure to accessorize with broaches, hair clips, cracked finger nail polish, cigarettes, and a gun.

3.) The Big Lebowski- I don't actually recommend that you dress like The Dude. Chances are no one will get your cheeky reference and assume that you are homeless or have unbelievably bad fashion sense. There is nothing appealing about The Dude's outfit of dirty shirts, pajama pants, and frumpy sweaters. He reminds me of my old, old landlord who used to only wear pajama bottoms that comfortably and articulately let his sagging ball sack swing.

4.) The Royal Tenenbaums- Again, chances are, if you dress like Margot or Richie Tenenbaum, people will think you are homeless, but at least you'll feel superior to them. For Margot, check out Craigslist for cheap fur coats and the American Apparel collared Leisure Dress. Make sure to throw on some heavy eyeliner and a frown, and the misunderstood tennis prodigies will come running! For Richie, grab your grandfather's suit from the closet and pick up some terry cloth headbands and wrist bands from American Apparel.

5.) Less Than Zero- Every morning I wake up and wish I look like Blair. It's true. However, my boobs can't fill a fitted tuxedo jacket if they tried! Less Than Zero optimizes 80's L.A., and boy, was that a fun time! The key to looking Bret Easton Ellis-like is wearing Ralph Lauren circa 1985, Oliver People's during the day, Wayfarer's at night, and tiny ring of blood around your nostril. Throw in a little hedonistic behavior and utter indifference to everything around you, and you're all set.

"Are you happy, Blair? You don't look happy."

"But do I look good?"

6.) Harold and Maude- The greatest love story ever told. It's not what you wear, but the glow of smitten that you give. Dress-wise, Harold and Maude look like they both collectively held up a Salvation Army. Actually, that is what the sequel was going to be if Maude didn't go and off herself (did I just spoil that for you?) The key to your outfit is not only the heavy jacket, but the scarf and 1971 haircuts. Make Bud Cort proud!

7.) Breathless- I'm going to share something with you right now that I don't want you to judge me for, ok? Ok? PROMISE? I've never gotten through The Big Lebowski and I was bored to shit during Breathless. There. I said.

However, I know that all you hip kids looooove both of these movies. The key to Breathless is looking all 60's-like. The Mia Farrow pixie cut and the anorexic body. That's all really. Oh!...and make sure to do slight cat like eyes with liquid eyeliner and maybe some pastel lipstick.