What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge.

It doesn’t get any better than June in Millbrook, with horse trailers winding down country lanes and the sights and scent of freshly cut fields; pointing to a summer season brimming with equestrian pursuits. All while friends and fans pull out their finest for the 25th Annual Mashomack International Challenge, signaling the start of the summer social season.


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge.
The Program arrived, hot off the presses!

Each year a visiting team arrives for some competition and camaraderie that is the essence of the sport. This year, Mashomack Polo Club will be entertaining our dashing and worthy opponents from the Philippines.


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge.

The excitement begins with great fanfare as the parade of international flags are led onto the field by the New York State Troop K Honor Guard, followed by the individual teams of mounted players.


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

The action begins as the teams take to the field to battle for trophy and country.


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

For what to wear to a spectacular spectators luncheon in the countryside we chose the brightest shades of white to kick off the summer in grand style. Happily, the younger set has been brightening the tent so this selection has something for everyone.

Since it is the 25th, I will surely be donning a hat. Our pals at The Madder Hatters will be in the boutique and open for a brisk business. Cult Gaia bags are so summer-fresh. Of course, wedges are de rigueur for grassy fields. And for the half-time divot stomp I have rediscovered the form and function of Stubbs & Wootton since they opened their Madison Avenue boutique — so comfortable and flattering!



In recent years, it has become a tradition for the younger generation to flock to this event, fresh from college and starter jobs to reunite with pals not seen since last summer.


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.
Go Next Gen!

What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

I’m hoping to entice Hilary up again for this year’s festivities. “If you are not feeling the white moment, I found some fun flirty colorful dresses to throw into the mix. They feel light and airy and perfect for a hot summer day to cheer on your team. And I couldn’t resist the polka dot in a nod to the infamous Julia Roberts scene in Pretty Woman. Add a wedge or espadrille, some fabulous sunnies, sunscreen in your tote, and you are off!”



What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.
Strapping on our wedges!

Following the match play, the Awards Ceremony takes place with presentations made by our generous sponsors.


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.
Jake Klopp won MVP!

Each we honor our friend, Mattias Guerrand Hermes, with an eponymous trophy for Outstanding Sportsmanship by a player.


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.
Clea, Valesca, and Lucien Guerrand-Hermes presenting the trophy to Don Langlois.

Here is a look-back through the years …


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

To enjoy watching a match, there are two main rules to note:

1. After a team scores, the play switches goals. This is unlike ice hockey where the team’s goal remains constant throughout the period.

2. The line of the ball is established by a player’s forward hit. Other players cannot cross the imaginary line that is projected without receiving a penalty. Like most rules of the sport, the impetus is safety for player and horses, or perhaps for horses then players.


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

Sadly, Mashomack Polo Club lost its #1 Fan this year when Gene Colley passed away, a day short of his 96 birthday.


Three Generations of Colleys 
What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.
Three generations of Colleys.

Gene’s son, Bruce Colley created the Mashomack International Polo Challenge 25 years ago, and revived the club when it had dwindled to a handful of members.


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

If you can’t make it up for the fun next Saturday, here is the seasonal schedule …


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

Or perhaps you want to try out a chukker or two …


What to wear to a polo match?  Celebrate the 25th Anniversary of Mashomack International Polo Challenge with spectating ensembles by Karen Klopp and Hilary Dick.   Best of summer fashion.

Photos courtesy of Peter T. Michaelis, Annie Watt Photography, Cutty McGill, Hilary Dick and Karen Klopp of What2WearWhere.com, who take the guesswork out of dressing, the legwork out of shopping, and the panic out of packing.©

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