With so many costume and clothing options Dead Rising 2 could almost be seen as a barbie doll sim. There's literally something for everyone, and unlike DR1 it isn't just colour swaps of the same suits over and over. 
 
So how do you dress up your Chuck? Like most I'm sure we're all constantly changing outfits, though some of my favourites come to wearing the Business Casual suit along with a black cowboy hat and boots, with some yellow tinted shades making Chuck look like one really deep pocketed Cowboy ;P. I also like to go around in Chuck's default outfit, too. That jacket really is damn awesome and Chuck suits it so fetchingly.... See...Dress Up Sim!

I wear the white leasure suit with a fedora and aviators. And black dress shoes. But if I'm not wearing that I just run around in a lizard mask and a mankini or something. Whatever floats my boat.

SWAT Uniform all the way, it just looks so badass I can't help myself. Followed by Black Tuxedo when I get bored of the SWAT Uniform from time to time.

While fighting slappy I accidentally picked up a hula girl outfit with my american flag motorcycle helmet. For some deranged reason I kinda liked it. 

Currently sporting the Champion Jacket after winning a Terror Is Reality match <3.

Mine has the little fake moustache and glasses, one of the showgirl headpieces, and a wetsuit with matching flip flops, I never stop laughing during the cutscenes where he's acting all serious with this fake moustache on hehe.

The Glasses with the nose and mustache on them, combined with the leather crotch-less Outfit from the sex shop is a great look.  

The Otis outfit, I have no idea where it came from, but I love it.

Currently rocking the TIR Champion outfit with default boots and yellow glasses. Oh and gray hair.

" Currently rocking the TIR Champion outfit with default boots and yellow glasses. Oh and gray hair. "

showgirl headpiece, avavior glasses and cowboy outfit

Skater clothes and blue hair.  I don't know why, it just works for me.  He looks way too muscular for it, though.  He needs to be skinny and trying to buy weed off me.

gay cowboy outfit, aviators and walking around with a "massager".

Ran around for a bit with the onesie PJs, groucho Marx glasses, and Frontier hat.
 
Now I'm running around with Bowling outfit and a shaved head.

White leisure suit, white fedora.  If I find a good black fedora and suit I'll switch to that.

In a tuxedo T-shirt

Am I the only one who dresses Chuck in a non-ridiculous manner?
 
I use the hunting jacket outfit from Case Zero, with Black Cowboy Boots and the TIR Cap. Looks so much better than default Chuck IMO.
 
BTW, are there any beards that don't look stupid? I've only found the full beard, which is a different color than Chuck's hair.

Black Cowboy Outfit, Black Cowboy Hat, Childrens Hero Mask.  Looks just like the Lone Ranger.  It's sweet.

Collegiate Ensemble  with no hat. I think I'm gonna pick up that SWAT uniform whenever I come across the store it's in. 

" Collegiate Ensemble  with no hat. I think I'm gonna pick up that SWAT uniform whenever I come across the store it's in.  "

Nothing but aviators... that's the way I go.

I've got him rocking a red onesie.

Tuxedo
White fedora hat
Yellow-tinted sunglasses

Overalls, big bushy beard, and blue hair.

I've had Chuck dressed as a SWAT police officer for a good chunk of the game, then kept my Tuxedo and black shoes after the Bibi (?) Psychopath/Survivor mission, and then went back to the original clothing near the end of the game.

Right now I'm rocking the superhero gear with blue hair.

I usually don't break the mold and just keep him as is.  But i did in the last hour decide to go dress up as a cowboy.  If felt pretty silly till...

Pink Hair, Yellow Tinted Glasses, Mesh Party Wear, and Black Cowboy Boots. 
 
It was so fucking awesome, but then I gave it all up so I could use Sports Fan to make the final boss easier. 
 
Damn it.

Tuxedo, black shoes, bald head and sport glasses. he looks like freakin' Hitman 47, it's awesome.

Barefoot, plaid suit, and a mohawk. When he gets covered in blood he looks punk as fuck.

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I've been doing the SWAT outfit with aviators and grey hair, makes Chuck look like a grizzled old cop. But then I add in the bunny slippers so you know he actually has a heart of gold.

Convict outfit, white basketball shoes, surgical mask (hygine mask?), bald head... kind of a reformed rapist vibe thats slowly going back to psychotic tendancies thanks to the zombies

Cowboy costume (as seen in quick look), but with a Blanka mask. It's hard to take cutscenes seriously.

A nice combo I've worked with is the business casual plus white cowboy hat and black cowboy boots. Makes Chuck look like one of those business Cowboys with some really deep pockets.