What to Wear to The International Gay Polo League Tournament

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This coming Saturday, April 9th, The International Gay Polo League Tournament comes galloping back to Wellington with an exciting lineup of lively events for a weekend of camaraderie, inclusion and spectacular excitement for all. Held at the International Polo Club Palm Beach, it is North America’s only high goal polo venue drawing top GPL players and avid spectators from around the globe for a weekend of grand horseplay.






Chip is a proud papa!

Chip McKenny, founder of GPL, describes the event in vibrant detail. “GPL celebrates the best of LGBTQ+ culture … color, energy, friendship, travel, and fun.  Whenever I am asked about the International Gay Polo Tournament, I describe it as the love-child between Burning Man and Pretty Woman.

“The Gay Polo League event is equally exciting for players and spectators – there are great polo matches and a knock-out tailgate competition.

“The Tournament is even more international this year! 16 LGBTQ polo players from 6 countries will compete next week.  Players are flying in from Argentina, France, Netherlands, New Zealand, Peru and the United States!”


KK, Chip, and dashing player.

Tomorrow (Friday) night, Polotini’s WIGSTOCK kicks off the festivities on a hilarious note with the legendary cabaret performer, Varla Jean Merman.

What to wear you ask? Vivacious fashion hits a high note for this affair!


Varla Jean Merman, self proclaimed love child of Ernest Borgnine and Ethel Merman!




Bold Choices for Wigstock

Amur Ruffled Midi Dress $598Amur Pleated Midi Dress $598  / Saloni Abstract Pleated Silk $598 Alexis Printed Maxi Dress $650  /  My Beachy Side Crocheted Fringed $386/  Edelman Platform Sandals $150  /  Stuart Weitzman Clog Sandals $450

Or perhaps this wig style is more YOU — in 22 colors!


On Saturday, April 9th, the gates open early at 9:00 a.m. and tailgaters flock field-side to set up the most creative and elaborate-themed pageants to vie for the Best Tailgate Award.







The Founder’s Cup Match begins at 10:30 a.m. followed by the Senator Cup Match at noon.   Spirits are running high as this year’s celebration will be sans mask in the Sunshine State.


Jack Lynch, KK and best playing pony.
Pam Taylor, Jennifer Kinsman, and friend.
A tale of two flags.

For what to wear, we felt the rainbow is a fitting motif for the tailgating tents as it is the symbol of Gay Pride. The flag was designed by San Francisco artist Gilbert Baker at the suggestion of Harvey Milk in 1978. Today, it is recognized globally but it was a revolutionary concept when first introduced.

Under the Rainbow

Dresses:  Rococo Sand Ombré White Mini  $368   /  ML Monique Lhuillier Satin Halter Mini  $445  /   Cami NYC Rainbow Dress $330  /  Accessories:  Rayban Sunglasses $159   /  Lack of Color Wide Brimmed Hat $139  /  Bari Lynn Headband  $21 /  Shoes:  Veronica Beard Platform Wedges $330    /  Veronica Beard Leather Wedge Sandals $350


The original flag had eight stripes with a specific meaning assigned to each color. It has been modified through the years to the pattern seen on the flag above with red as the lead shade, comparable to an actual rainbow.



A current and final version now hangs in the MoMA, Museum of Modern Art collection.  From the catalogue: “The rainbow flag is a symbol of pride and community that was first unfurled at the San Francisco Gay and Lesbian Freedom Day Parade on June 25, 1978. Led by Baker, the flag’s designer, thirty volunteers gathered at the Gay Community Center in San Francisco to hand-dye and stitch rainbow flags for the parade to highlight the acceptance and equality of sexual and gender minorities as both a global struggle and a matter of civil rights. The contemporary, mass-produced version of the flag in MoMA’s collection celebrates the accessibility and worldwide adoption of this humble masterpiece of design.”



Of course, Hilary has embraced the Rainbow Spirit with her signature panache. “This year is all about bright colors. And what a perfect weekend to wear them all! The brighter the better to cheer on the players from all over the world.”

Hilary’s Rainbow Brights

Dresses:  Staud Pink Dress $325  / Baobab Blue Skirt and Top Set $220  /  Xirena Yellow Puff Sleeve  $294  /  A.L.C.  Green Poplin Mini Dress $495  / Et Ochs Pink One Shoulder $995  /   Jonathan Simkhai Red Dress $445  /  Shoes:  L’Agence Yellow Sandals $495  /  Aquazurra Pink Satin Mules $995  /  Alexander Wang Green Strappy Sandals $550

And for what to wear to the tented fieldside luncheon and Sunday’s Brunch & High Goal Game, our look is decidedly more demure.  The subtle shade is a nod to rosé, the beverage of choice for these games. It is the perfect neutral for spring and the upcoming holidays of Passover and Easter as well as the seasons beyond. A casual sun hat, sunglasses, and the de rigueur footwear of wedges or thick-heeled sandals complete the essential ensemble for the half-time divot stomp.

Coming Up Rosé

Dresses: Zimmerman Linen Dress $495  /   Maje Ruffled Dress $385  /  Shoshanna Floral $440  /  Baum und Pferdgarten Jacquard Midi $399  /  Hats:  Barbour Striped Hat $65  /  Gigi Burris Raffia Hat $375   /  Shoes: Jimmy Choo Pearl Studded Wedges $650  / Castaner Woven Platform Sandals $365  /  Rayban Sunglasses $159

Not a sport for the faint of heart!


When the dust settles, the fiercest of rivals become fast friends as the teams celebrate the grand international sport they all love. As Winston Churchill once proclaimed, “A polo handicap is a person’s ticket to the world.”


The First Republic Team with Stephen LaRochelle.

In April 2021, the GLBT Historical Society received an archival donation of an extraordinary, unique piece of history: a fragment of one of the two monumental rainbow flags first raised on June 25, 1978 in San Francisco’s United Nations Plaza at the San Francisco Gay Freedom Day Parade.

For more history of the movement, visit the GLBT Historical Society.



Photos courtesy of: Phelps Media Group, KK, Patrick McMullan, GLBT Historical Society.


Karen Klopp and Hilary Dick are the Founders of What2WearWhere.com. We Take the Guesswork Out of Dressing, the Legwork out of Shopping and the Panic Out of Packing.™ 

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