Ivy Style at The Harriman Cup

By Matthew Longcore

The 42^nd annual edition of the Harriman Cup Polo Match took place on Saturday, September 19^th at Bethpage Polo at the Park in Old Bethpage, Long Island. J. Press was the main sponsor of the event.

Established in 1985 and named for polo player and former New York Governor W. Averell Harriman, the Harriman Cup is an annual match between teams from Yale University and the University of Virginia. Proceeds from the event support the undergraduate polo programs at both universities. The event is recognized as America’s oldest alumni polo match.

Played before one of the event’s strongest crowds in recent years, the 2026 match brought together generations of players and supporters to celebrate the longstanding collegiate polo tradition between the two universities.

This was the fourth time my wife and I have attended the Harriman Cup. We always have a wonderful time at this event, but this year was particularly memorable for several reasons.

Our very cute dogs, Bella and Gigi, sported stylish Yale Bulldogs scarves. These two adorable girls garnered a lot of attention from event attendees. Together they won the “Best Dog Award” at the 2026 Harriman Cup.

This year I also had the honor of being invited to serve on the board of the Harriman Cup. My new role includes serving as a liaison to the media. Our guests at the Harriman Cup this year included writers and publishers who have been featured in Ivy Style including Alec Dent, Karlton Miko Tyack, and Justinian Mason.

The Harriman Cup has a longstanding reputation as one of the best dressed events of year. In terms of sartorial splendor, it rivals other famous sporting events like the Henley Royal Regatta, Royal Ascot, and the Kentucky Derby.  In 1999, The New York Times covered the Harriman Cup when the event was held at the Ox Ridge Hunt Club in Darien, Connecticut. The article which begins “RALPH LAUREN, eat your heart out” provides a history of the event and highlights the stylish attendees.

Ove the past four years, my wife and I have enjoyed the opportunity to join the well-dressed. Each year, I have worn something very much in the classic tradition of Ivy style – a navy blazer (2023), a madras sport coat (2024), and a seersucker sport coat (2025). This year I wore a tan poplin 3/2 roll sack suit with a made in USA pink oxford cloth button down shirt and a Yale bulldogs bow tie, all from J. Press.

Yale and UVA played an exciting match which culminated in a 7-6 victory for the Bulldogs. Needless to say, for this Yale alumnus, the 42^nd annual Harriman Cup was a perfect day.