WWIB: I Feel Pretty



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Finally a “Who Wears It Better?” where the contestants will actually care about the winner! Well, at least I assume any guy dressed up as a lady would want to know if he looks better than another dude dressed as a lady. I’ve seen the movie Birdcage, so I’ll consider my knowledge of the subject to be above average. So, which guy/gal is dressed to impress?

Alabama & Arkansas

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Rating: 6.5/10 (131 votes cast)
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WWIB: I Feel Pretty, 6.5 out of 10 based on 131 ratings

23 Comments, Comment or Ping

  1. Jen

    Daughter to dad: “Stop borrowing my sh*t!”

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    February 13th, 2013

  2. Cybr

    I’m going with the left. He looks like a little more thought went into the outfit. Though the guy on the right has a decent set of MOOBS.

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    February 13th, 2013

  3. LaLD

    The guy on the left, although blurry or because of being blurry, looks like Billy Bob Thornton.

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    February 13th, 2013

  4. hex

    dudette on the right looks like he’s sporting a easter basket for a hat..

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    February 13th, 2013

  5. jason M.

    Raoul Duke is looking like shit!

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    February 13th, 2013

  6. Evie

    I kind of love them both. However, I would share a closet with the guy on the left. He is fierce and fashionable.

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    February 13th, 2013

  7. Eric

    The guy on the right looks like Ozzy.

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    February 13th, 2013

  8. kitty

    girls just wanna have fun….. or wait their dudes!

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    February 13th, 2013

  9. Northerngirl

    Why is the guy on the right wearing an Easter Basket on his head?

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    February 13th, 2013

  10. Hypno Toad

    Rocky Horror vs. Twisted Sister

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    February 13th, 2013

  11. girlwatcher

    I only have one question. Which one are you saying is dressed like a “LADY”?

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    February 13th, 2013

  12. Eric

    I’m not convinced that the one on the right isn’t in fact a really ugly woman. (those boobs look genuine)

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    February 14th, 2013

  13. Count Flatula

    The one on the right looks like my friend’s wife. OMG!

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    February 14th, 2013

  14. Succubus' sister-in-law

    I’m surprised that, seeing these pics were taken in the South, they’re not getting a beatdown by homophobic hillbillies.

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    February 16th, 2013

  15. Emma

    The dude on the left, the one on the right needs to go over to the hair salon and do something about that mess.

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    February 17th, 2013

  16. Emma

    Most certainly the guy on the left….The one on the right looks like (s)he belongs at Bonarroo.

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    February 18th, 2013

  17. Lindsey

    The guy on the left is rockin’ it. I like his shoes and leggings. If that’s a mustache I see, he gets extra points.

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    February 20th, 2013

  18. Casey

    Left. I so want to steal his heels. Also I feel so girly for saying that…. Though one on the right is rocking the jeans.

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    March 2nd, 2013

  19. Rachel

    The one on the right goes to my local walmart on almost a daily basis…he tells everyone that he is a she….

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    March 9th, 2013

  20. Robbie Brooks

    Lord, I saw this guy 3 times the other day. The guy with the white wig.. Even submitted an updated photo…

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    June 6th, 2013

  21. Shelley

    The dude on the left looks like Vince McMann from WWE. Ijs

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    July 24th, 2013

  22. c

    The guy on the right looks better. Although the purple skirt doesn’t go well with the outfit…

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    August 18th, 2013

  23. Hayli

    Is it sad that the one on the left is a 77 year old female that goes to my church? I found this hilarious and had to show her!

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    December 10th, 2013

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