Adam Sandler has more money than God, a comedy production empire that will churn out movies forever and ever, a wife and kids, and the consistent blockbuster appeal anyone would kill for. (And a bevy of gorgeous fictional mansions.) What he does not have is a tailor, apparently. Sandler generally shuns formal wear, but on some occasions manages to don a suit or even a tux — though he always looks pretty uncomfortable. Journey with us through some of his odd fashion choices, where his discomfort is apparent, his suits ultra-voluminous, and his ties way, way too long!
If you had to predict Stephen Dorff and Adam Sandler's careers back when this photo was taken, what would you have said? (This is not long after Billy...
If you had to predict Stephen Dorff and Adam Sandler's careers back when this photo was taken, what would you have said? (This is not long after Billy Madison came out.)
Photo: Jeff KravitzThis is a 100 percent appropriate outfit for the 1996 ESPYs. Or the ESPYs today, honestly. But for the love of god, just stand up straight!
Photo: N...This is a 100 percent appropriate outfit for the 1996 ESPYs. Or the ESPYs today, honestly. But for the love of god, just stand up straight!
Photo: New York Daily News Archive/1996/Daily News, L.P. (New York)Everything is a size too big, but this is pretty cute.
Other than the forced doofiness, this is actually fine.
Photo: J. P. AussenardOther than the slime, courtesy of the Kids' Choice Awards, this tux is actually decent.
Photo: KMazur/2002 Wireimage.comHigh-water mark. Not coincidentally, in this photo he's promoting Punch-Drunk Love, also a career high-water mark.
Photo: Tony Barson ArchiveSandler's Punch-Drunk Love era will be remembered as his most decently outfitted.
Photo: George Pimentel/? 2002 WireImageJust...tie the tie right. Come on.
Photo: New York Daily News Archive/2002/Daily News, L.P. (New York)He cleans up nice!
Photo: Getty Images/2003 AdamSandler.comIf you can get a dog's suit tailored, you can get your own suit tailored.
Photo: Getty Images/2003 AdamSandler.comIs there a law that prevents Adam Sandler's ties from being tied correctly?
Photo: SGranitz50 First Dates is not as good as The Wedding Singer, but both have their merits.
Photo: Frank Micelotta/2005 Getty ImagesThe one time he's legit pulled together, it's in the ugliest suit in the world. Sigh.
Photo: Jeff Vespa ArchiveDoes that have to be so shiny?
Photo: Gareth Cattermole/2006 Getty ImagesThis isn't so bad. A little on the boxy side, certainly, but we've seen (and will see) worse.
Photo: Ethan Miller/2007 Getty ImagesIn general, you want the bottom of your tie to be right around your belt. Just FYI.
Photo: Sylvain GabouryButton that top button, straighten the tie, pull the jacket down a little. See? Fixed.
Photo: Ferdaus Shamim/2008 Ferdaus ShamimDoes that jacket have to be so voluminous? Tailoring is everyone's friend.
Photo: Kevin Winter/2009 Getty ImagesTHIS SUIT IS TOO BIG.
Photo: GABRIEL BOUYS/2011 AFPMaybe the suits all fit wrong because spiritually Adam Sandler is just not a suit guy? He looks so, so uncomfortable.
Photo: James Coldrey/2011 James...Maybe the suits all fit wrong because spiritually Adam Sandler is just not a suit guy? He looks so, so uncomfortable.
Photo: James Coldrey/2011 James ColdreyHuge tie, huge jacket, huge pants — streamline! Just streamline everything.
Photo: Stephen Lovekin/2011 Getty ImagesWhose jacket it that? It's 10 sizes too big for Sandler.
Photo: Michael Tran/2011 Michael TranI'm Adam Sandler, and I own the longest tie in the world!
Photo: Mr Photoman / Splash News/?Again with the tie. Just tie it correctly!
Photo: Frederick M. Brown/2012 Getty Images
