Wink, Wink

Meet Nancy Gordon, a veteran writer, editor, publisher and designer, whose fond memory from childhood led her to create a sweet new business called Pillowinks.

There is an air of playfulness that surrounds Nancy Gordon. It comes out in her smile, the wave of her hands when she is speaking, the rising lilt of her voice. But there also is a sense of “she means business” about her. And that combination was just right for turning her creative spark into a product that melts hearts.

Gordon is the creator of Pillowinks, which stemmed from a special encounter she had as a child with her great-grandmother Lena, or GG Lena. Pillowinks are pillowcases with a “wink” embroidered on the top and they have a secret pocket that can be filled with gifts, wishes and more. Gordon’s introduction to the idea was in the form of a white handkerchief filled with candy.

“GG Lena was a very cool and inspiring lady. She lived in New York City and sewed hats for the Ziegfeld Follies. She always wore black with a white lacy handkerchief pinned to her chest,” Gordon recalls. “When I was about 4, I was spending the night at my grandmother’s house when GG Lena was there for a visit. Just before bedtime, she called me over and whispered that there was a present for me next to my pillow. Then she held my shoulders, winked and smiled. I ran straight up to bed and found, wrapped in one of her lacy white handkerchiefs, a handful of Charms candies. My favorites! I felt soooooooo special.”

At that age, Gordon had not yet mastered the art of winking. 

“The next morning at breakfast, I wanted to thank GG Lena with a wink, but I could only blink,” she offers. “After too many blinks and everyone staring at me, she finally understood, reached over, gave my hand a big squeeze, smiled and winked.”

Gordon, who was born in Plainfield, New Jersey, says she was “quietly adventurous” as a child. Her formative years were a time of trial and error but brought her into the orbit of luminaries such as writer and filmmaker Nora Ephron; author, producer and screenwriter Nicholas Pileggi; and graphic designer Milton Glaser, perhaps best known for his iconic I Love (Heart) New York logo.

Gordon with Whittaker

“My young adult years were mostly about discovering who I was and how to fit into life in New York City,” Gordon shares. “With a college degree in International Relations of the Soviet Union, I had read a ton of great literature and was suited for nothing. Happily, my parents had met Esther Margolis, the VP at Bantam Books. She got me a job as the secretary to the art director. All I did was file book covers. I stayed about eight months and, after watching the designers, decided to be a freelance graphic designer. My first freelance assignment involved creating double-ruled borders for photographs. I had never used a ruling pen. I called the Bantam design department and begged them to help me. They did the job for me. After I turned it in, I realized that faking it to this extent wasn’t going to work. However, after a number of uh-oh experiences (At one studio, I inadvertently cut a piece of original artwork in half. I was mortified. They fired me.), I called Esther and she got me an interview with the art director at New York magazine.”

Gordon was hired to paste up the classified ads in the weekly magazine. 

“I had a migraine for the first three weeks and little cuts all over my hands from the razor blades, but what a place to cut your teeth … Ephron, Pileggi, Glaser…” she notes. “I stayed for eight years and even ended up on the cover of one April 1980 issue posing as the executive-type neurotic patient in a therapy session. Hilarious fun and my week of fame!”

Gordon took a year off to design fabric, wallpaper and rugs, which she sold to showrooms, but then went back to New York magazine for a short spell.

Among other endeavors, including, until 2019, publishing Zest magazine in Maine while living in Florida, Gordon got the inspiration for Pillowinks. She had moved to Ocala 16 years ago because she found northern winters “less and less tolerable” and wanted to live on a property that could also be the home to her beloved horse Whittaker.

It was one morning after riding Whittaker, when she was giving him a bath, that “into my brain popped the gift that my great-grandmother Lena had given me. The memory made me smile all day.”

She says her pillowcase idea felt “right” and she hoped she could figure out how to make it work. It took about two years to bring her idea to fruition. She had to navigate design work, fabric choices, packaging, shipping and more, and says she got a lot of help along the way.

“I created Pillowinks to honor GG Lena,” she says, “and to give people the opportunity to make their loved ones feel as special as she made me feel.”

The pillowcases are made of white organic cotton with a “wink” embroidered in Sweetheart Pink, Cove Blue or Old Lace on the outside top cuff. The secret pocket is easily accessible on the inside bottom cuff. For every six Pillowinks sold, Gordon donates one to Boston Children’s Hospital.

Gordon finds comfort in tucking a lock of Whittaker’s hair into her own Pillowink. Testimonials on the Pillowinks website reveal a variety of “gifts” being secreted into the pillowcases, such as a rosary, tickets to the ballet, a small carving of a duck and a ring.

When two longtime friends spent a night together, one of them put a black and white childhood photo into the other’s Pillowink.

“We stayed awake most of the night crying, laughing and talking about high school and those days of growing up. We had the best time!” the recipient wrote.

One young woman posted a very special remembrance, recapping how her boyfriend texted her a photo of him winking. She says she checked her Pillowinks pocket and “there was a treasure hunt map leading me to our favorite beach. He was there, kneeling on a beach blanket, and asked me to marry him,” she shares.

“I love the testimonials,” says Gordon. “Such sweet stories and a lot of creativity. I love reading about the joys that Pillowinks brings people.”

Through the years, and especially in the two it took to bring Pillowinks to market, Gordon says one bit of advice has held true for her.

Gerald T. Counihan, the associate art director at Bantam Books, told her, “The saddest thing in life is getting to the end and saying, ‘I wish I had,’ because you could have.”

“At 23, his words stuck, and I’ve lived my life by them,” she shares. “It’s the reason I didn’t give up on Pillowinks.” OS

To learn more, go to

Posted in Ocala Style FeaturesTagged

Share this post


What's New at Ocala Style

Ocala Cooks | Lisa Dorsey

Lisa Dorsey is a longtime resident of Ocala who loves...

Ocala Cooks | Leslie Callahan

Leslie Callahan is a patient advocate at The VA Villages...

Ocala Cooks | Scott Mitchell

Scott Mitchell is the director of the Silver River Museum...

Ocala Cooks | Maggie Weakley

Maggie Weakley and her husband, Kent, both noted local artists,...

Transplanting for Summer

May is a good month to move plants around your...

From Stranger to Friend (in one conversation)

Turns out, the family’s dog walker was stealing the expensive...