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6 Horrible First Date Outfits

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Ever since Ashley’s Children’s Lit Fashion Spread post, I’ve been obsessed with Polyvore.  I almost wish I had one of those day jobs where I was bored shitless all day to have more time to play with it.  Almost.

So what better way to out use to Ashley’s great discovery than for me to judge who you are, based solely on a one-time hypothetical appearance!?  As my old pal Method Man would say, it’s Judgment Day.

1. Anne of Green Gables/Little House on The Prairie

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I’m actually fairly guilty of this one.  I have way too many of these types of “pieces” such that they will inevitably collide one day.  Just be careful not to wear them all at once, because then your date might think you belong to the Victorian equivalent of some Civil War reenactment club.

2. Hi, Maybe You’ll Somehow Think I’m Kate Moss

Again, nothing necessarily wrong with the pieces individually (that eagle claw Pamela Love necklace I especially like), but if I see this combination of flower dress/black boots/black tights/leather jacket one more time, I’ll be thoroughly convinced that most of the women of NYC have reached rock bottom in the creativity dept. I’m fairly sure that your date will not somehow be convinced that you’re Kate Moss, given the sea of imitation Kate Mosses walking around. If you’re that personality-less, this will just drill it home for your date even more. However, if you just really, really have a thing for Kate Moss that much, my advice to you is to incorporate some key elements of her style into your own, as opposed to making yourself a (bad) carbon copy.

3. Hey, I’m Sexy! Didja notice!?
I saw a girl wearing a very similar version of this outfit on the train, and thought: “Man, I really hope that’s a costume for a play.” I think there is only so much leather and “sexy” cues people can take before it gets tedious, and well, hideous. I’m going to go ahead and say that garter belt skirts are never okay to wear as part of a public outfit, period. Not to mention, that the whole thing just screams “I wish they would just make Barb Wire 2 already”.

4. Barbara Hernandezz
Ashley and I have discussed at length the “Barbara Hernandez” (mispronounced Hernan-dehhhz, with no emphasis on the 2nd “a”, of course) phenomenon. This “trend” is usually a more problem with 40-to-50-something upper middle class white women who love Chico’s and have traveled to the third world. Though, I’ve definitely met some Barbara Hernandez Jr.s out there, who, upon returning from their summer abroad in Guatemala, all of a sudden think that co-opting the native culture of a third world country will actually make them more interesting or legit. Unless your date is of the same breed, I say, tone down the hippie skirts and eighty pieces of craft jewelery. Also, stop being an idiot.

5. AA Nightmare
This is the Skipper to Barbara Hernandez’s Barbie. Skipper, in this case, loves to co-opt other cultures, but doesn’t really give a shit about colonialism or history or anything. She just wants to look ironic, even though she’s not quite sure what that means. If you can believe it, this dress is from a collection called “Afrika” at American Apparel. Yes, seriously. If you’re wearing any version of this outfit and your date doesn’t vomit on you, then they’re probably a horrible person…just like you.

6. Lindsey Naegle
Basically, a date with anyone wearing this would be like when Maude Flanders dies, and Ned Flanders goes out on a date with Lindsey Naegle. I mean, if you really like to dress like you’re going to work all the time, just try and tone it down a bit with jeans instead of a pencil skirt, or a tank/pencil skirt combo, with maybe a more casual hairstyle.

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Anna G - Caliburg Contributor

Anna G - Caliburg Contributor

Anna G. is a Southern California native living in the Williamsburg area of Brooklyn since 2005. Anna is constantly trying to unite her love of CA sunshine and the excitement of the New York urban jungle, all the while trying to keep her unwieldy credit card debt under control, and look fabulous at brunch, no matter how un-showered and hungover.


  1. Broke-Ass Stuart - Editor In Cheap
    October 13, 2009 at 9:55 am

    I’ve always loved that photo of the fat kid!

  2. November 21, 2009 at 9:46 pm

    haha, i just love that first outfit!

  3. hi
    August 30, 2010 at 10:44 am

    LOL I love the teva sandals outfit