I've noticed that a lot of characters in games must spend 3 hours or so in front of a mirror choosing their outfit. Which is why i've made a short-ish list of the most stylish characters in games old and new (more new than old).
Altair - Assassin's Creed
There's something that makes Altair look slim and stylish in his white robes. The fingerless gloves are a nice edition as well!
Captain MacMillan - Call Of Duty 4
I don't know but that Ghillie suit makes MacMillan look cool, maybe it's the circular head or the leaves?
Marca Ragnos - Jedi Knight : Jedi Academy
Any Sith lord that sports the 'ripped cloth and chains' look is bound to make this list.
Any Dremora - Elder Scrolls IV : Oblivion
The Demonic Armor look is a dead cert for a fashion list.
Master Chief - Halo:Combat Evolved, Halo 2, Halo 3
This would not be a fashion list without Master Chief, period.
Your Agent - Crackdown
No matter which face you pick, by the time you get 4 stars strength level, you look cool.
Slash - Guitar Hero III:Legends Of Rock
Slash is the coolest dude EVER. He's in a game, 'nuff said.
Gordon Freeman - Half Life, Half Life 2, The Orange Box
His suit is just the pinnacle of style.
Bowser - First appeared in Super Mario 64, i think.
His spiky shell could make a geek look cool.
Yoshimitsu - Tekken series
At the point when he pulls out his laser sword, he is the daddy of style.
Thief (I don't know his name) - Thief, Thief II
The hooded look just fitted him perfectly....
Delta 07 - Star Wars:Republic Commando
All of the Deltas looked mint, but 07 had the best personality.
That Red Toa - Some Crappy Bionicle Game.
He's the best looking Lego dude ever, shame the games sucked...
Lara Croft - Tomb Raider Series
She had geeks everywhere doing their own washing for months....
Any Mii Character - Mii Channel
They look soooo odd but sooo cool.
Well thats it, I know i left some out. Maybe I'll do a fashion disaster some other time.