A lot of young men ask me how they can elevate their sartorial game. They live in smaller cities, perhaps, and people give them a hard time when they dress up. Or maybe they work in offices that are on the casual side and don’t want to stand out. It can be hard to dress better than your boss.
Establishing your sartorial identity isn’t always easy, especially when you’re not getting reinforcement from people around you. These things don’t happen overnight, unless you live in a family of Naples tailors.
But here are some ways to make things easier.
1/ Embrace the Rule of Three. When you wear something with a certain amount of intensity for the first time, like white bucks or a light linen jacket, people might give you a hard time. Try to brush that off without being defensive. Even make a joke at your expense. “I’m channeling Dickie Greenleaf.” The second time you wear it they’ll be used to it. The third time it’s your thing. You’ve worn them down and can declare victory.