If a character is stranded and can't get a change of clothes then sure, but really... If someone knows they're going somewhere, they should bring a change of clothes. Clothing is a lot about personal style, or what TV is trying to sell you on style - reminds me of the Hannah Montana era of Disney where all the girls had long shirts and jeans and a "belt skirt" that went around the fattest part of their hips that was a mix of fancy belts and scarfs. Or some kind of splosh of color in that area to trick your eyeball.
Crow has no sense of color style, thus the blue sweater with pumpkin orange pants. HAHAHAHA. But he had achromatopsia for the last 5 years, soooooo
Will on the other hand wears a bit more variety, and yet less, since he's a noble.
I actually have tried really hard to keep both Will and Crow specifically in a harmonious color scheme so I can take pretty much any outfit they wear and pair them together without losing sight of their styles. If Crow gave Will one of his button-ups, Will would button it up all of the way and the cuffs, and Crow is more likely to leave the cuff's unbuttoned and not button it up all the way either at the top, bottom or both, and likely wouldn't tuck it in.
Reminds me of the clothing design for Smith's character in I.Robot; When he wears his hat, it only covers one ear.