There are celebrities, and there are icons. But how do you become the latter? It usually starts with some talent and charisma, then, one day, a skilled photographer comes along and snaps a picture that turns into a poster, an advertisement or a magazine cover. The image becomes a classic. And so does the woman.

But aren’t sensual images like this the opposite of feminine power? After all, anyone can pose in skimpy clothing or show some skin. We say, the true lady legend understands that her sultriness is just one small aspect of her appeal. The photo may catapult her career, but she knows it’s up to her to reveal her more intellectual talents and worldly charms to have staying power. … //READ MORE

This is a photo of Bronx, New York,-born Sylvia Bergman Kopstein, taken around 1931, when she was 21 years old. Both Sylvia and her twin sister, Blanche, embraced the fashions of the times. They loved to dress up in fitted skirts, cute hats and sweaters—including this sweater coat with a fur collar, which Sylvia most likely made herself.

She and Blanche hung out together at the Fishkin Sisters Knitting store in The Bronx. They both had many dates and sometimes, when one of the twins had double booked or just didn’t feel like going out, tried to fool the guys by passing themselves off as the other. The sisters also double-dated and attended lots of dances. They did the Charleston and the Black Bottom, which were popular at the time. They donned pastel chiffon and satin dresses, and put henna in their hair to get it reddish. Sylvia stayed red her whole life. Blanche dyed her hair blonde in her younger years, but later in life switched to Sylvia’s color, Honey Red … //READ MORE

This is a portrait taken of my mother, Cynthia Mays Nicosia, in the late 1950s when she was in her early 20s and studying dance at the Metropolitan School of Ballet in Manhattan. She was working part time at the New York City Public Library on 42nd Street and living at the Brandon Residence For Women up on 85th Street near Riverside Drive, which was run by Volunteers of America. She paid $17 a week for room and board, which included breakfast and supper. However, because she was usually training late into the evening at ballet school, she would often miss the dinner.

In 1961, just a couple years after this photo was taken, my mom dashed off to Rome to see about a dancing job. She ended up not getting the gig, but she decided to make the most of her time in Italy. She took a tour of the city called “Rome By Night.” My dad, Giorgio Nicosia, was the guide. Cynthia and Giorgio first exchanged words at the fountain of Trevi. At the end of the tour, he dropped off all the other passengers first and then took my mom back to her hotel, where he asked her out. They had about three dates before she had to … //READ MORE

This is a photo of my Aunt Dorothy in the early 1930s when she was a young woman. At the time, Aunt Dorothy and two of her friends loved to sing together and they formed the Silver Trio, which performed at evening clubs in the Moline, Illinois, area, so I think this may have been a professional photo. I can remember when we used to take the three-hour train ride from Moline to Chicago and our first stop would be Marshall Field’s, where we could find the latest hats, makeup, gloves and, of course, dresses. I think Aunt Dorothy’s favorite purchase was shoes, but she looked smashing in all the fashions of the day—from dresses with butterfly sleeves, nipped waists and midi-length skirts to peep-toe pumps.

Aunt Dorothy became a working woman during World War 2 and continued working throughout her life. In her retirement years she helped to organize another small group of women and they had a wonderful time entertaining at various retirement communities. This year, Dorothy turns 104! She now resides in Florida with her second … //READ MORE

When I look at this photo of my mother, Phyllis, taken in 1963 in Brooklyn, New York, for her high school yearbook portrait, the first thing I notice (besides the beehive hairdo) is how mature she looked for a teenager. In fact, all high school seniors looked pretty sophisticated back then. Maybe it was the solemn expressions they were encouraged to make right before the 35-millimeter camera flashed, or perhaps it was the pearls, sweater sets and bowties that were de rigueur back in the day for formal portraits. I like to imagine my mother, sitting in front of her etched mirror in her mid-century bedroom, teasing her locks into a glorious pouf, then meticulously drawing cat eyes with liquid liner, to prepare for the event. It was my fascination with photos like these of my stylish young mom that inspired my own taste for 1960s fashion—minus the Aqua Net hairspray—and probably one of the reasons I’m a fan of Madmen culture. Betty Draper, eat your heart out.

Do you know a remarkable woman who made a style impact back in her day? Send us her photo, and she could be next to star in Red Typewriter!

This photo of my grandmother, Nina Popova Kapanadze, was taken in Sukhumi, the capital of what is now considered the Republic of Abkhazia, on the eastern coast of the Black Sea, around 1954. Grandma Nina’s style has always been classic and tailored, and she’s only worn clothing that suits her perfectly. I love how happy and relaxed she looks in this picture, as she poses seaside in a polished gingham dress and walking sandals. It must have been a good day.

Grandma, now 92, has never worn anything off the rack. She’s either made her own clothes (a great skill to have during war rationing) or altered store-bought ones. In the 1940s, when trench coats were all the rage, she stayed up all night making herself one to wear to the premier of a traveling circus show the following night. Grandma and Grandpa were lead dancers in the city’s biggest dance troupe, so they never had a problem securing the best tickets to any show in town. Needles to say, no other woman at the … //READ MORE