28th Annual Harriman Cup

It's become our Labor Day, our summer's end, our last ditch effort to let it all hang out of our seersucker trousers—the annual Harriman Cup. Rain or shine, throngs descend upon the Meadowbrook Polo Club from Manhattan and surrounding bed and breakfasts. We roll in off the LIRR in a blaze of vintage Lilly, Ralph Lauren, and Brooks Brothers—the usual suspects. Usually falling on or around the last week of summer, this alumni polo match between Yale and the University of Virginia is the tailgating event of the summer for the prep set (last year's Cup was a ball).

Of course, awards are given out for such displays of leisurely grandeur. Best dressed, best hat, best tailgate, and so on. Max Sinsteden has just rolled out his generous tattered oriental rug under his champagne bucket stand and various hor d'oeuvres. It’s a nice spread. However, a neighboring goldenrod Land Rover with blonde hair, blue-eyed college alum promises to be stiff competition. Their snacks are nothing more than finger sandwiches and pretzels, standard fare. Turns out it's Sam's tailgate...and we discover she and Fred work together at Ralph Lauren. That's the nature of the Harriman Cup, you’re two degrees from anyone in a navy blazer.

Vintage Lilly Pulitzer, patchwork madras, and seersucker.

Van, Cooper, Max, and Fred.

Max Sinsteden with his tailgate squad.

Thanks to Town & Country, we spend most of our time in and out of the VIP tent this year, and frankly, we're quite spoiled with the experience. Booze, food (we go back for seconds on the pulled pork—shameless, we're aware), the deceptive feeling of self importance—all on the house thanks to the handful of sponsors like J.Mclaughlin, Knockaround, Vitamin Water, and many more. Seriously though, the best time to be had is mingling from tailgate to tailgate while only casually glancing at the match between cocktails.