Point-to-Point Pointers

Amid speculation of dire weather and to the shock of many revelers, Sunday May 5 turned out to be a fabulous day for the 30th Anniversary of Winterthur’s annual Point-to-Point. Always being an amazing excuse for men to wear as much plaid and pastels as possible and women to wear the most exuberant hats they can find, we found this year’s revelers proved to be no exception. After scouring the scene to find those in attendance who put out the most effort to make a splash…here are some of the best of the best at this year’s event as well as some tips on how you can start preparing now for next year.


1)      For a terrific woman’s headpiece, find the hat with the most feathers. If you think it’s too much don’t worry—it’s not.

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2)      Creating a sure-fire, attention-grabbing men’s hat is easy: 1. Find a hat and place the tallest thing you can find on it. 2. Add some plastic horses to run around it. 3. Drink heavily before and during the event.

3)      It’s all in accessorizing. This year’s “best” was to simply place a teeny, tiny dog in a Dunkin Donut Munchkins Box and off you go!

4)      If you come with an injury it’s nice to try to coordinate the injury with the outfit.

5)      Always match your tailgate table. Always.

6)      Want to stand out from the crowd? Lots of bright colors and a glass of champagne will do the trick.

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7)      If you have a horse, dress the part.

8)      If you have a horse and a carriage, you still need to dress the part.


Just remember for next year: If you think your outfit might be a little “too much,” don’t worry, it won’t be!


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