A Photo History of Adam Sandler’s Troubled Relationship With Suits
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 Kravitz
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: 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. Aussenard
Other than the slime, courtesy of the Kids' Choice Awards, this tux is actually decent.
Photo: KMazur/2002 Wireimage.com
High-water mark. Not coincidentally, in this photo he's promoting Punch-Drunk Love, also a career high-water mark.
Photo: Tony Barson Archive
Sandler's Punch-Drunk Love era will be remembered as his most decently outfitted.
Photo: George Pimentel/? 2002 WireImage
Just...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.com
If you can get a dog's suit tailored, you can get your own suit tailored.
Photo: Getty Images/2003 AdamSandler.com
Is there a law that prevents Adam Sandler's ties from being tied correctly?
Photo: SGranitz
50 First Dates is not as good as The Wedding Singer, but both have their merits.
Photo: Frank Micelotta/2005 Getty Images
The one time he's legit pulled together, it's in the ugliest suit in the world. Sigh.
Photo: Jeff Vespa Archive
Does that have to be so shiny?
Photo: Gareth Cattermole/2006 Getty Images
This isn't so bad. A little on the boxy side, certainly, but we've seen (and will see) worse.
Photo: Ethan Miller/2007 Getty Images
In general, you want the bottom of your tie to be right around your belt. Just FYI.
Photo: Sylvain Gaboury
Button that top button, straighten the tie, pull the jacket down a little. See? Fixed.
Photo: Ferdaus Shamim/2008 Ferdaus Shamim
Does that jacket have to be so voluminous? Tailoring is everyone's friend.
Photo: Kevin Winter/2009 Getty Images
THIS SUIT IS TOO BIG.
Photo: GABRIEL BOUYS/2011 AFP
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...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 Coldrey
Huge tie, huge jacket, huge pants — streamline! Just streamline everything.
Photo: Stephen Lovekin/2011 Getty Images
Whose jacket it that? It's 10 sizes too big for Sandler.
Photo: Michael Tran/2011 Michael Tran
I'm Adam Sandler, and I own the longest tie in the world!
Photo: Mr Photoman / Splash News/? www.splashnews.com
Again with the tie. Just tie it correctly!
Photo: Frederick M. Brown/2012 Getty Images