The stylish button-downers would engage in a form of sartorial one-upmanship that brought wild dollops of golf course color or tartan-inspired outrageousness into classic ensembles that made insiders smile while outsiders wince.
— Alan Flusser from Style and the Man
I remember back in my college years we called them “F–k You Pants”—referring to the message you sent by wearing them. After graduation I moved from the South to NYC, and packed inside my sole piece of luggage, an army duffel bag, was a pair of madras plaid trousers. They were Polo and they ate up half my monthly GI Bill stipend, and I was not happy to learn that in NYC they were called “Jack Ass Pants”—referring to the wearer himself and not his ballsy attitude.
Whatever you call them—and for present purposes let’s go with Go to Hell Pants—Madras is a good place to start. The fabric’s lighter than your average chino twill, and the pattern—while eye catching—isn’t overly, obnoxiously colorful.
Lilly Pulitzer is the classic label, but serious GTH cognoscenti deem her far too popular with preppies to be taken seriously. J McLaughlin offers a tied waistband version ($125) that you won’t see coming and going. This pajama bottom-like pant reminds me of another Lilly-like designer and mother: Carla Beerman, who created Tinkers, a charming wash-and-wear PJ pant with wild prints. Sadly, Tinkers is gone, but CEGO shirt makers in NYC can replicate a pair for an affordable $100.
If you really want to make a statement, and have a story to tell, search out your own fabric and have a custom pair made. Legendary sportscaster Bud Collins goes to Charlie Davidson at the Andover Shop in Cambridge for his signature trousers. Ask nicely and Charlie will whip up a pair for you ($185-$200). The aforementioned Alan Flusser offers full bespoke at $495. And if that number scares you away, well, that’s why Gilt MAN was invented. Check Gilt’s daily sales (noon ET, but you knew that) for trousers from the likes of Masons, Incotex, and Marc by Marc Jacobs.
A word of warning, though. While you can, and should, wear these trousers with a sport coat, they are not to be worn to work. These are occasion trousers and with that comes the responsibility of time and place. The time is summer. The place is near water and within arm’s reach of a G&T. Going sockless helps, and a half lined navy blazer in linen keeps you respectable, while the dash of Ray-Ban aviators kicks you into the classic GTH look. True devil-may-care attire always requires forethought.
No one does GTH (the trousers and the ‘tude) better than Flusser. Click through the slideshow below for a tour through his personal collection.[smooth=id:114;]