If you want to look like you're part of the established upper crust, Matland encourages you to follow Roman's lead instead of Tom's (sorry, Cousin Greg). Tom Wambsgans joins the Roy family by dating and marrying the only daughter, Shiv. 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 Tom'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."