I wear two pairs of socks, fur lined boots, two pairs of pants with long johns underneath, two shirts, 1 sweatshirt, 1 body warmer, duffle coat, thick gloves, flying helmet.
I too have tried to play chess while ice fishing - the two activities do not mix well.
A Wisconsin-Kight!
I love living by the dells, the waterparks are sweet.
I usually wear whatever i'm wearing at the time....
I usually enjoy playing online chess wearing my birthday suit. 
Lets see...i wear underwear sometimes.....pants on occation....and a shirt rarely.
Seriously, terrible question. I wear just regular everyday clothes.
the truth, i dont play the online chess, i play the live chess.
the truth, i dont play the online chess, i play the live chess.
so just sun glasses and sandals?
Rings on my fingers and bells on my toes? A s##t eating grin?
Well usually I wear a white robe, my royal headdress and some gold here and there. Then I have to consult with Sia and Imhotep before I make my move (gods of knowledge and wisdom)
maybe it would be nice to have the option of having webcams during internet chess to actually be able to see your opponent, but there would probably have to be some kind of small premium charge to set it up...and it would kind of change the character of the game...just trying to think outside of the box folks!!!
T-shirt, short pants and slipppers.
I put on my robe and wizard hat.
Horned Viking helmet and battle axe.
Spandex, flip-flops, tank top, hard hat, and my Elton John sunglasses of course
...gimp outfit
pimp suit, green stripped suit with a puple t shirt, white gloves with three white lines going down them and a pimp cane rests on my chair.
I dont have a special outfit for playing live chess, no one's going to see it after all. The only thing I HAVE to wear not only for playing chess but to concentrate on anything (study, wargames, drawing...) is socks and shoes. That one is a MUST.
Pa-nts?