Karen Pillsbury spent 22 years as an Army wife, moving from base to base, raising her kids and keeping up with the daily grind. But once her children were grown, she found herself with time on her hands—and a need for connection. That’s when she discovered the Red Hat Society (RHS), and life hasn’t been the same since.

“It has opened my eyes, gave me independence and gave me a reason to get away from home and be a person of my own,” said Pillsbury.  

Like many women, Pillsbury spent years caring for others. She didn’t realize how much she needed something just for herself.

“The Red Hat Society has helped women of all ages [who are] struggling gain confidence and independence to get out and be social again,” Pillsbury said. 

RHS is all about fun, friendship and a splash of fabulousness (with red hats!), helping women of a certain age rediscover joy. 

When Pillsbury first heard about it, her immediate concern was cost. 

Red Hatters and friends Jean Iliff, Wavey Williams and Karen Pillsbury enjoy the spring weather from a park bench outside the Citadel Mall. Photo by Rhonda Van Pelt.

“Sometimes we don’t even know what’s out there that won’t cost an arm and a leg to be involved in,” she said.

Chapter fees are minimal—some as low as $10 and others free. There’s a $35 annual membership fee for the national organization. 

“The way the economy is, everything costs so much to do,” Pillsbury said. “As women having to balance the household budget, we never allowed money for us to just relax and enjoy.” 

A Widefield resident, Pillsbury, 68, belongs to two chapters: the Purple Stars and the Krazy O’Kootz. She’s made countless friends and explored Colorado through sightseeing trips. 

Karen Pillsbury creates springtime plaques from Dollar Tree supplies. Photo by Karin Hill.

She’s also grown as a leader. As Prime Mistress of the Colorado Springs Queens Council, she helps oversee more than 20 area RHS chapters, including Pueblo, Monument, Falcon, Peyton, Woodland Park and Widefield.

Chapters are led by queens, not presidents, and officers often hold whimsical titles to match their lively personalities. 

Queen Helen Baker, 82, said her chapter, The Country Chix in Peyton, calls the member who sends out event notices the “Email Female.” 

The Monumental Red Hatters dub the member who picks delicious dining spots the “Duchess of Lunches,” said Sandi Watson-Staggs, 74. 

CULTIVATING INTERESTS

“That is what is so unique about the Red Hat ladies,” Pillsbury said. “We get to know the ladies and try to match them with the chapters that do the things they like to do.”

Prospective members usually chat with Outreach Chairman Watson-Staggs to discuss hobbies and schedules so they can be matched with the right group. 

Chapter activities are as diverse as the women themselves. Some gather for home luncheons, crafts or day trips. Others dive into book clubs, quilting, shopping or movies. Pajama parties and alpaca farm visits? Those happen too. 

Some chapters offer a spiritual focus. Gianna Jacobs, known as Lady Sonshine, is queen of The Victorian Jewels, a Christian chapter. 

Charitable work is at the heart of some groups. Wanda Sypher, 90, vice queen of The Red Hat Lady Bugs, said her chapter has supported The Salvation Army, Ronald McDonald House and Safe Passages. Other chapters collect socks and toiletries for nursing homes. 

Jan Coulier, 87, queen of The Scarlett Sisters, said her chapter adopts a local family each year and provides gift cards and financial support.

THE START OF SOMETHING FABULOUS

All this camaraderie, discovery and amusement began with a unique birthday gift. 

In 1997, RHS Founder Sue Ellen Cooper gave a thrifted red hat to her friend, along with a copy of Jenny Joseph’s poem “Warning,” which begins: “When I am an old woman I shall wear purple with a red hat which doesn’t go and doesn’t suit me.”

Annette Steele, Claire Steele and Marty Tuggle from the Krazy O’ Kootz chapter meet at IHOP for breakfast and crafting. Photo by Karin Hill.

 The look stuck. In April 1998, RHS was founded as a “playgroup” for women approaching 50 and beyond. Now a global organization, RHS celebrates its 27th anniversary this month.

Locally, many women have been part of RHS for decades. Some are widows who find that Red Hat events are their only regular social outlet, said Sypher.

Since COVID-19, a few chapters have struggled. Pillsbury hopes to reignite interest in places like Pueblo, so the sisterhood continues to grow. 

SISTERS IN SCARLET 

Women of all ages are welcome to join, but only those 50 and older can don the iconic red hats and purple attire. Younger members wear pink hats and lavender clothing until they “REDuate” into their bold “big girl” colors on their 50th birthday. 

Out in public, RHS members’ signature style turns heads, eliciting curious looks from some—but smiles of recognition from others. 

“It’s always the men that come up and say, ‘Oh, you ladies look so nice. My mom is a Red Hatter’ or, ‘My grandma was a Red Hatter,’” Watson-Staggs said. 

Traveling Red Hatters often find instant kinship. 

“Ladies that may be vacationing here say, ‘I belong to a Red Hat group in California’ or wherever,” said Watson-Staggs. 

That global recognition—and bond among members—makes the Red Hat Society special.

Every year, the Colorado Springs Queens Council hosts a regional bash filled with food, entertainment and camaraderie. This year’s event is set for September 24, with a few hundred attendees expected.

The RHS International Convention is August 10-13 in San Antonio, Texas. 

Sypher encourages curious women to ask a Red Hatter about joining.

“If you want to have a lot of fun and listen to some jokes and be entertained, join the Red Hats—and make new friends,” Sypher said. 

“Real friends,” Pillsbury added.

To learn more, visit RedHatSociety.com or ColoradoSpringsQueensCouncil.com. Prospective members can also email Sandi Watson-Staggs at [email protected]. She asks that prospective members be ready to join when they contact her, as finding the right chapter takes time and effort.