Who Wore It Best?

Filed under: Who Wore It Best

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LEFT: Brad Pitt at Santa Barbara Film Festival’s Tribute to Angelina Jolie

RIGHT: Boogie Nights’ Dirk Diggler on the hunt for all sorts of ‘blow’

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Posted by Candy2 ♦ February 3, 2008

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21 Responses to “Who Wore It Best?”

  1. Julie

    Mmmm…..Jesse James for the win.

  2. martini lover

    dirk diggler gets my vote. brad is looking old and tired these days.

  3. those two make me sick. with their fake smiles and such. two huge, publicity whores. and again, another beautiful outfit pulled off by angelina jolie.. NOT. i actually went cross- eyed from looking at that skirt. wayyy too many patterns. and as much as i dislike them, angelina is pretty no doubt, but fuck, she has really been displaying a shitty and awful taste in clothing as of late. get it together ang!!

  4. oh, and definitely dirk diggler hands down takes this one. brad looks boring, and quite old in this pic. side note: brad, would it kill you to smile?

  5. Ohno

    Clint Eastwood looks younger than Brad. I’ll go with DD and his massive schlong.

  6. afurrica

    Dude, you’re 44 years old. That ‘hair’ is not fooling anyone.

  7. c'est moi

    the pic of dirk is hilarious!!! he wins

  8. Jenn F.

    Those are some pretty nasty outfits on both Brad and Angelina.

    Dirk’s definitely working the lounge suit much better.

  9. Jo Jo

    Brad looks good in anything.

  10. Happy Go Lucky

    Okay Brad’s suit is nicer but Dirk looks WAAY better. Also, what in the hell is angie wearing.
    Good lord, that is some ugly shit! seriously,
    dress UP when you’re the guest of honor

  11. Vern

    Brad must have said:
    “If you’re really wearing that ugly dress I’m gonna wear my Barry Manilow circa ‘72 wig with my child pornographer scruff!”

    Dirk is totally rocking the collar!

  12. Bobofet

    Oh dear…don’t go the vest route just like freako Tom Cruise. Makes you look 20 years older.

  13. OMG!

    I’m actually gonna vote for Marky Mark here.

    Yikes!!

  14. WTF! Brad looks like Leisure Suit Larry (…Jen got out just in time).

  15. 'Sup

    BIG UPS bluehawaii!…Jen totally got out in time. Brad looks like a man who left his beautiful marriage that needed work (imagine that, actually working on a marriage), married his hoochy co-star, took on her 3 kids, had one of his own…and, well, dude looks beat.

  16. hey, age doesn’t matter. brad is a hunk and the chicks still know it.

  17. i remember when we guys all looked like porn stars, which comforted us through all those lonely nights. hahaha

  18. Ah, the 70s. Maybe he’s getting ready to star in a Ron Jeremy bio–guess they’ll have to find somebody to do the stunt work for the twig and berry shots.

  19. Bee Hind

    My mom wore a similar outfit on New Year’s Eve in 1974.
    Her hair was much bigger than Angie’s though.

  20. I thought Brad was channeling Glen Campbell and Angie was working one of Dorothy Sbornak’s old schmattas.

  21. Mezza

    Dirk, is that you? Shit-a-brick, mate, i thought it was Harry Hamlin as outfitted by Greg Brady.

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