You should just stick to the Dior look. Wear button downs from Dior and Raf, get a knit or two, and pair them with black chelseas and black derbies. Then slowly acquire outerwear piece by piece, get stuff like Dior or Balenciaga peacoat and grab some Lad Musician too if you want.
hagg burn that vile shirt, swap out sneakers. jeans good
Tennis players wear this kind of outfit casually. It's not high fashion, but there is nothing wrong with it either. I doubt you will see many players wearing Rick t-shirts on the court, or just off of one.