On the other hand, Roman, born into the Roy family wealth as the youngest son, dresses with a casual cocktail of confidence and disdain. Tom's clumsy attempts to dress the part often are the very reason he stands out, but Roman is the inverse of that. He can skip his tie, wrinkle his button-down, and still look like he belongs. Anyone can buy an expensive suit, but only the likes of Roman Roy can casually flex his wealth by wearing a six-figure outfit in the most "whatever" way possible.
The lesson: If you're trying too hard, it'll look like you're trying too hard. Carrying yourself with confidence will get you much further than gifting Logan Roy with a Patek Philippe watch.