Affectionately known as “The Hat Sisters” to their legion of fans and friends, the Hat Sisters have worn their unique and colorful hats on untold number of occasions to help raise money for, or draw attention to, a worthy cause.

The Hat Sisters

While a significant number of their charitable efforts benefit the LGBT community, many serve a broader audience.   One such program is The Boston Globe’s Scholastic Art & Writing Awards for junior and senior high school kids, through which young people receive visual arts and writing awards and scholarships. For this, they don’t don the incredible hats they design and construct, but for most others they do, such as the American Heart Association’s Heart Ball.   At The Muscular Dystrophy Association’s HEEL Ball, shoes are the main draw except for the Hat Sisters’ hats of course.   At the Arts in Bloom event, for the Boston Museum of Fine Arts Art, the Hat Sister’s not only designed their own hats but also many of the hats worn by the fashion models.

As their presence is in such demand, the Hat Sisters sometimes maintain a rigorous schedule with as many as three different events in one day and, of course, twice that number of hats need to be designed and constructed. Even their old hats serve a charitable purpose as they donate them to organizations like Rosie’s Place, a Boston organization that supports the homeless, for auction.

The Hat Sisters happened quite by accident.   John Michael Gray was in Provincetown preparing for the second Provincetown Carnival in 1984. While talking with his significant other, Tim O’Connor, who was back home working in Boston, he spoke of all the costumes and parties he’d seen, and asked Tim what they should wear. Tim’s busy schedule prompted him to leave that up to his hubby. “I’ll wear whatever you wear,” he said. With that, John Michael began to create, making two of everything, identical and colorful.

Longtime friends join Tim (L) and John Michael (R) at their 25th Anniversary Celebration

The very first hat and costume, Crying Doves, sat atop “much, much younger and thinner guys,” laughs Tim. It was made from a simple, white Speedo combined with a pair of flip-flops on a baseball cap covered with white feathers and a painted orange bill. White cloth was attached to the back of the cap, and cuffed fabric to each of their wrists. When they raised their arms, it had the effect of wings - and The Hat Sisters were born.

Most of the hats worn by the Sisters are guided by a theme, color, invitation, or other details marking the event they are attending. Their favorite hat was created in 1987 for the March on Washington.   Right there in the garage of the Hilton Hotel in our Nation’s Capital, Tim constructed two Washington Monument hats. “It was spectacular,” Tim recalled.

Everyone Wants Their Photo Taken with The Hat Sisters!

The pair laugh as they consider the many “hat parts” they have in “satellite” locations. Some are in a storeroom in Boston, and others are in their spare bedroom in Provincetown, stored lovingly in transparent boxes. The hat parts are cataloged by decoration type: flowers, fish, animals, boas, etc. If ever you see them wearing a hat that you absolutely love, grab a camera and click a picture—quickly—because, as John Michael declares, “We wear them one time, and they come apart at the end of the day. You might see pieces of a hat combined, reused, or mixed with other hats, but each new hat only lives once!”

They say in unison, “That’s part of the game.” This is an essential element that keeps it interesting for them, because they never really know what each day or hat will bring. After spending just a few minutes with the guys, it’s more than their “image” that comes alive. Tim removes John Michael’s pearls before a photo shoot so their outfits match. John Michael examines their pumps and hats carefully to ensure that each detail is in place. They often finish one another’s sentences.

It’s a lot of work to put these elaborate hats and outfits together and now that they are both retired they have more time, but even when they both worked full time jobs it didn’t slow them down. For them, it is and always has been a labor of love. They love doing it and that they can help others by doing so. As John Michael puts it, “When it stops being fun, the Hat Sisters will be no more.” And that will be a sad day for all who have benefited from the joy and generosity that these two men have brought to so many.

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