Watching a grown man trip down the sidewalk in court-jester shoes made me giggle. And these style mavens were soooo serious, dahling...
Have men become a group of effeminate elves? The shoes curl up at the point. It’s embarrassing for women to wear those sorts of shoes. On men, it takes 50 million years of mammalian evolution to suppress the primal urge to laugh and point.
Fashion, however, is utterly a matter of taste, as is most of what we call masculine or feminine. As far as this native-born Texan is concerned, you can take my pointy-toed, 1.5 to 2-inch heeled, decoratively embroidered boots after you've pried them from my cold, dead hands.
Fashions change. Today, the Utilikilt folks are waging a guerrilla marketing campaign to convince Americans that kilts are manly. The ancient Romans of the early Republic would have needed no convincing, however, as they felt that "bifurcated" garments like pants were feminine. They also felt the toga was the final word in conservative, serious clothing and wore socks with their sandals. Sometimes, the more things change, the more they really do, in fact, change.
Clothing and fashion are fun to play with in RPGs, too. Want to make a place seem a bit alien? Have people dress oddly. Pierced noses, formal tattoos, body paint, and odd headgear can all lend an air of the exotic. It's even more fun if those odd twists of fashion actually make sense. Things like pattens or chaps make sense in the right environments.
Unfortunately, you can take it too far. Nobody wants to read your five pages explaining the fashion faux pas of the various lands and cultures of your campaign. Dribbled in as these different places are visited, however, can be fun. As with all else, moderation.
Yeah, I know, the players assuming that the wonky LotR movies' bizarre waistcoats-and-cloaks fashion is all the rage in your campaign world can be very annoying. But it is their game, too, and too much oddness makes the game impossible to invest in. If your players are a bunch of anthropology majors and fashion mavens, sure, go hog-wild with sadors and philactories. Otherwise, less is probably more.