This outfit would look try hard on anyone. You’re just willing to forgive if the person is very handsome or someone for whom the clothes obviously fit their lifestyle. They don’t get forgiveness because they’re not handsome or tradesmen.

That’s why it’s so important to understand context. If you’re good looking, you can wear anything. Literally. You can wear sweatpants and rag t shirts and still look good. If you’re not good looking, you can still dress well but well has to be appropriate. Don’t be a lawyer dressed head to toe in brand new Carharrt or hypebeast sneakers. Wear a suit, or trad, dress well for your lifestyle, not for a totally different lifestyle that isn’t your own.