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.
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.
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  • Reply Angie April 14, 2010 at 5:19 pm

    All great suggestions! Although walking around town like The Dude might scare people, it could make a great Halloween costume.

  • Reply KeLLy aNN April 14, 2010 at 5:43 pm

    You forgot Cornnuts!

    hahaha, some great choices.

    I was a teenager/young adult in the 80s so at some point I've dressed like all of that.

    Love cardigans,esp my dads old ones.

    Never seen Breathless, but I groove to black eyeliner and pink lipstick everyday. I save the cat eyes for date night!

    Wayfarers, any time, day or night, is just plain, CooLness

  • Reply April April 14, 2010 at 6:17 pm

    Sadly enough, my current style most closely reflects The Big L's. Grad school is hard, yo. And it's probably good that I'm getting into character now as I may find myself broke and homeless in a month.

  • Reply Hipstercrite April 14, 2010 at 6:21 pm

    @Angie- As popular as the dude is, I've never seen someone dress as him!

    @Kelly Ann- Wait, what's the Corn Nuts?

    @April- Hahaha…that made me laugh so hard…

  • Reply bard April 14, 2010 at 6:24 pm

    I was going to feel guilty about never seeing Harold and Maude, but if you can't get through The Big Lebowski we have other problems to address first.

  • Reply VegKat April 14, 2010 at 6:49 pm

    I actually bought a red white and blue polyester Lacoste polo dress at a vintage store (it even has a red belt *sigh*), but it was a size too small. So now I'm reducing so I can be a mopey Margot. I even have the stringy, poker-straight bob. Now I just need to hack my finger off in a wood chopping accident with my Amish birth family.

  • Reply Sophie Neutron April 14, 2010 at 7:13 pm

    Not really related: I don't get when people don't like fur coats "because it's murder" but they love steak.
    Yeah beef is vegetable meat. Like spinach or mushrooms. Organic of course!

    Kinda related: I NEED to get some wayfarers for dark time coolness/hiding that I'm actually asleep in the corner of the club/bar/wherever.

  • Reply Juliette April 14, 2010 at 7:14 pm

    Great suggestions! They are all hipster worthy.

    Favorite movie idols are the ones that you always reflect on and that cause you to see an article of clothing or something and say, "hey, that reminds me of…"

    -Juliette WhereForArtThouRomeo

  • Reply piecing it together April 14, 2010 at 8:19 pm


    this changed my mind about skorts. this will change your mind about skorts. i'd be lying if i said i wasn't wearing this RIGHT NOW.

    "kelly, that skirt is awfully short…"

    "no, no, no, it's okay, look…IT HAS SHORTS."

  • Reply Amber April 14, 2010 at 10:25 pm

    I think at one point or another I've dressed like every single cast member in Dazed and Confused (both accidentally and on purpose).

    I actually sort of dig The Dude's sweater. But when putting together a big lebowski ensemble the most essential article of clothing would probably be the jellies, which, according to imdb, belonged to Jeff Bridges.


  • Reply KeLLy aNN April 14, 2010 at 11:42 pm

    the main chick Heather, in Heathers had a thing for corn nuts.
    And when wynona and christian gave her that glass of cleaner? she drank it, grabbed her throat, and said "corn nuts".

  • Reply TheBigShowAtUD April 15, 2010 at 3:07 am

    you and Jewish eyebrows, huh?

    i think if anyone's going to dress like The Dude, it must be done either for Halloween or while bowling… or while bowling on Halloween.

  • Reply LiLu April 15, 2010 at 5:56 pm

    I've never seen Less Than Zero, but after this, I really want to.

  • Reply Paula April 15, 2010 at 6:01 pm

    I can't make it through Breathless either. But! True story—in high school, some equally lame friends of mine would play Heathers with me…namely, we'd wear red, green, yellow…and then have Veronica. Sadly, there was no Christian Slater type to fill that role, nor was there any murderin'. (Ok, and also, nobody knew what the hell we were doing…which only added to the cool.)

  • Reply tomgfoto April 15, 2010 at 10:24 pm

    Have you ever tried watching 'the Dude', while drinking a caucasian?

  • Reply That Chelsea Girl™ April 16, 2010 at 4:50 pm

    I just recently watched Heathers for the billionth time…great, funny post as always. Take care!

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