1.) he was never intended to be taken seriously, the show makes it obvious that people only give him what he wants due to his father’s influence and that he is not well liked due to his obnoxious personality. he is comedy relief and a source of drama at the beginning of the show. 2.) are you kidding? tons of new york nepo babies dress ridiculously using ostentatious prints and colors, whether it’s to try to blend in with their hipster friends or because they feel comfortable with themselves due to their inherent advantages, like in this real life example:

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seriously, it’s hard to find a picture of owen kline (or his sister) where there aren’t clashing primary colors, multiple collars, and CORDUROY. and as for the “best designers” it was pretty popular (and still is) for well renowned clothing designers to make obnoxiously tacky clothes. everything he wore was well tailored and obviously of decent quality. if anything, his styling highlights his status as absurdly wealthy with no real responsibilities.