I obviously I don’t know Tom Brady, but from a conventional perspective the man is as Alpha as they come. Add in the anectodal evidence of how hot is wife is and how fiercely she defends him, and it’s safe to say the man is a natural with some tight game.
Unfortunately he can still look like an idiot if he dresses poorly.
You only want one stand-out piece at a time. The cardigan, the hat, and the glasses would all be cool on their own, but when you put them all together it makes even super-alpha Brady look like a high-school Junior who spent his Christmas money at H&M and was too excited to space out every thing he was wearing throughout the week.
I’m all for fashion and peacocking, but it’s smart to do it with one, maybe two pieces at a time. Don’t look like a costume.