Modes of dress are one of my favorite little details to add to a character. I only wish they came up more often in-game. I don't think I've ever worn anything even vaguely resembling medieval clothing, however - my fashion influences tend to be somewhere in between anime or high-fantasy stylings.
Loopmotten Scheppen (the First), my barbarian/battle sorcerer - made with a base AC of 8 and no inclination to wear armor, to match his desire to teach his weird fighting style far and wide (one of his favorite comments is to point out that they can't hit you if their swords are lodged in your torso, though this strategy has for some inexplicable reason failed to win many converts) - wears thin alabaster silk trousers, a matching sleeveless mantle showing off his oddly-muscled physique, sturdy leather gloves, and inexplicably heavy fur-lined boots made of frost worm hide (which was quite a trick to get, since they explode into ice when you kill 'em). The right-hand glove is actually a glove of storing holding his weapon, a cursed falchion by the name of Finality.
Adauth Mirorwyn is a bard/marshal who I play as the ultimate preparedness guru. He uses the bardic knack variant from the PHB II and a variety of skill-boosting tricks, spells, and items (including the martial auras) to keep competitive skill ranks in virtually every skill. As you might expect, his theme is pockets. Normal pockets, pockets worked into his armor, magical pockets, hidden pockets, pockets for poisons and alchemical items and swimming gear. He is festooned with pockets. Other than that, pretty standard - green forester's cloak, a concealed mithral chain shirt, mithral dastana, sturdy boots, practical clothing - except for the complex baldric he uses to stash his heavy platinum fullblade. Nothing says "I spend too much time training" like a weapon of choice that requires not one but
two Exotic Weapon Proficiencies to use properly.
Tikkarus Shael Vuk, my Zilargo gnomish Technologist - yes, I asked the DM to let me play a character class I wrote myself (see sig) - is a bundle of ill-fitting clothes wrapped in a heavy leather duster that clanks and rattles and occasionally sloshes as he moves, since he basically uses it as a laboratory on the go. He's the Shaq of gnomes, though - 3' 8"! - so most of his clothing doesn't fit especially well, since he uses untrained Craft (tailoring) checks to resize them for his frame. The duster is actually fitted for a human, so it just envelopes Tikkarus. He's sewn chain links into key parts of it as well, some of which show and some of which don't, making for the equivalent of a masterwork chain shirt. He frequently has some kind of spidery construct held in his hands as well.
) So for him, we're talking a duster for a coat, leather pants, silk shirt, all very *non* period.
IIRC, it actually had some mechanical effects to things like moving silently and the possible effects of caltrops.
