Simon Cowell has his own special way of wearing clothes, which is to say that he doesn’t wear them well. It’s something we established a long time ago. He is dedicated to excess fabric like Lenny Kravitz is dedicated to limiting it on his person; a little pleading from the Internet will not change him. That said, because designers and brands are banking on looser fits right now, identifying where fashion and Cowell diverge seems like a worthwhile endeavor. Especially when it comes to suits. Because if you’re going to wear a relaxed-fit suit, you want it to look cool and intentional, not like you haven’t changed your wardrobe in two decades.
Cowell stepped out in a suit this weekend, and we couldn’t help but notice his missteps. For starters, his jacket is long and lean when it should be short and boxy. At least a little bit. Slimming down your suit jackets to fit your torso and create a nice v-shape is a pro move, don’t get us wrong, but when it comes to a relaxed fit suit, you don’t want it to dart in quite so sharply. The same thing is happening with his pants, too. Good-looking loose-fit pants come in two cuts: carrot shape—looser through the seat and thighs, tapered and cropped at the ankle—and baggy allover—pleats, pooling hem, the works (see AMI, below). Cowell’s pants are neither. They’re slim in the waist and hips and baggy down below. Like a reverse carrot shape; one step away from bell-bottoms.
If Cowell was wearing bell-bottom suit pants in some crazy Jimi Hendrix-level brocade fabric a la Harry Styles, that would be one thing, but his suit is all business in terms of fabric and color. Unless you’re going full Balenciaga norm-corporate, opt for suit fabrics and colors that would feel more at home in at a house party than a board meeting. And style the suit like that’s where you’re headed, too. Cowell’s pointy boots are not inherently bad, but a big suit is a lot easier to pull off when you’re wearing chunkier shoes. And his shirt? That’s a post in and of itself. A button-down shirt with a loose-fit suit is fine, but unless you’re actually on the runway, unbuttoning more than two buttons at once is ill-advised.