I’d never dress like Paul Simon, but I can’t help but to admire his style. Decades before mixing sportswear with tailoring became a menswear cliché, Simon used to mix and match things from his closet with free verve – white t-shirts with pinstriped business suits, ball caps with tweed and denim. A documented advocate of floppy knit ties and soft-shouldered sport coats (something I would wear), Simon’s style complemented his work as a musician. It was classical, but not sterile. It was thoughtful, but not rule bound. It also had a kind of youthful naivety that made things feel playful, whereas lesser men like me would look twee in such ensembles.
Stylistically, Simon’s best period was when he was romantically involved with Carrie Fisher. Simon proposed to her at a Yankees baseball game, then they got married in 1983 and divorced the following year. But their romance lasted much longer – almost five years after the divorce, at one point with the two still living together. In his book
Even with all the fights and sadness, you can see some tender moments in these photos below – Simon and Fisher at parties, sometimes in matching outfits like jersey knits with suits, or more traditional business casual for upscale restaurants. Aside from a couple of fashion-forward sport coats, Simon seemed to prefer classic cuts with a two-button configuration, welted pockets, and four-button sleeves. The shoulders were soft; the lapels moderate. The coats were on the slightly more formal side of things, compared to a three-roll-two and patch pocket set-up, but he dressed them down with denim, t-shirts, and sports caps. When he layered a v-neck sweater over a dress shirt, his collar would poke out like it would on a schoolboy dressed up for picture day.
Some things here I think anyone can wear. The rustic, tartan red shirt with a brown suede jacket is a great look for autumn; the navy sport coat with khaki chinos and a burgundy knit tie is a reliable combo year-round. Others are a bit more daring. In one of the color photos below, you can tell Simon’s shirt was originally made for a woman since the placket faces right. He wears it with a drapey, light blue sport coat made with a low gorge and extended shoulders.
But the more charming ones here often ride the line. Simon pulls off the sport coat and denim look well. He finds tees that are just long enough to cover his belt line, so he can wear them untucked with tailored jackets. The five-panel caps have shallow crowns, which looks a little better with his more classically inspired ensembles. He occasionally accessorizes with a muffler, which I used to write off because they’re not long enough to properly wrap around your neck (Simon just lets his drape). All in all, there’s something boyishly insouciant about these looks. They’re of a man who clearly cares about how he dresses, but doesn’t fuss over dimples. He has fun with his clothes. And even if I wouldn’t copy these outfits, there’s something so right about them.