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Highly punchable face.
I've watched this show a few times. I generally dislike everything this guy wears except for the blazers and stripe ties. I don't really like the character. He beds hot women left, right and centre but when I look at this guy pouting I think this guy can't possibly be straight.
It's called a dandy... seriously guys, if you're confused why a guy like this beds hot women, read "The Art of Seduction".
I never watched the show (odd I have a Chuck Bass avatar though), but I know they were really expensive clothes (Lanvin, BoO, etc.) from reading blogs. I am sure they have stylist team who already have all of the clothes and rent or lend it to the cast for the show.