First of all, if you’re going to accuse The Menswear Guy of snark based on moral judgement, it’s worth noting that the Duke of Windsor was an unequivocally AWFUL person. He struck a deal with Hitler to let Germany conquer Britain so he could be king again. But he was one dapper motherfucker.
A lot of times, I ask myself a lot why it is someone like Ben Shapiro would come begging to you for fashion advice like there’s some x+y=z secret code to being fashionable. (Yes, The Menswear Guy has shown screenshots of Ben Shapiro’s assistant asking him for fashion advice.)
When the fact is there is no real formula to being fashionable, you have to express yourself and take genuine pleasure in what you’re wearing. Ben Shapiro has never felt pleasure in his life without hating himself afterwards.
When you treat fashion as a status symbol and not something you love and find joy in, you will never be a fashionable person, which is something that respectability and conformity-minded conservatives will NEVER understand.
