If you want to look like you’re part of the established upper crust, Matland encourages you to follow Roman Roy’s lead instead of Tom Wambsgans, which means aim for an effortless look, rather than one that feels contrived. Wambsgans joins the Roy family by dating and marrying the only daughter, Siobhan “Shiv” Roy. He’s portrayed as an outsider from the start, trying way too hard to fit in from the first moment we meet him in episode one. In fact, one of the only things all of the Roy children bond over during the series is criticizing Wambsgans’s fumbling sartorial attempts.
“The idea of matching your tie with your pocket square and suspenders is absolute nonsense. For anyone with real money, that would be an immediate giveaway that you’re posturing and trying desperately to show something,” Matland explained of the nuanced field of landmines that make up sartorial choices among the 0.001 percent. “People like Tom equate fashion with finance, and those two things have nothing in common. It’s also something as subtle as the width of a pinstripe on a suit. Tom’s is a little bit more pronounced whereas you would never see that on Kendall. If you saw a pinstripe it would be micro — on Tom, it’s just a stage too intense.”
On the other hand, Roman Roy, born into family wealth as the youngest son, dresses with a casual cocktail of confidence and disdain. Wambsgans’s clumsy attempts to dress the part often are the very reason he stands out, but Roy is the inverse of that. He can skip his tie, wrinkle his button-down shirt, and still look like he belongs. Anyone can buy an expensive suit, but only the likes of Roy can casually flex his wealth by wearing a six-figure outfit in the most carefree way possible.
