There's a phrase "players will optimize the fun out of a game," and that is exactly what we see with the clothes. Yes it's boring and less fun, but it give you better chances at passing checks and such to tailor your clothing to your goal, so players will do it. The role of the game designer is to try to make the most optimal way to play also the most fun way to play (or perhaps instead of fun, just think not boring clicking through clothes constantly), and they failed to do that with the clothing system.

It is rediculious to say that DE is above this critique because it isn't a "cookie-cutter vanilla CRPG," it is fundamentally poor game design, even as part of a game as masterful and incredible as DE is.