Frank Olive was born in Milwaukee, Wis., in 1929. He began his fashion career in San Francisco designing costumes for a dance company. He eventually moved to New York hoping to become a designer for Broadway productions. In the early 1950s he opened a store in New York named La Boutique. Although he also designed dresses, hats quickly became Frank Olive's specialty. By 1971 Olive had established a new boutique named Frank Olive's World focused primarily on millinery.
His designs took inspiration from men's headwear but featured crisp lines and feminine details. During the 1960s, when the fashion world largely eschewed hats, Olive continued to thrive by creating headwear to match the collections of specific designers including Oscar de la Renta, Adri, Pauline Trigere, Giorgia Sant Angelo and Gloria Sachs. Over time Olive produced hats under numerous labels including Frank Olive New York, Counter-Fit by Frank Olive, Frank's Girl, and Private Collection.
In his prime Olive estimated that he designed up to 1,500 hats per year, each based on one of 15 basic styles. Frank Olive specialties included the Watteau, the bush hat, and the swagger hat, first made famous by Greta Garbo. Frank Olive hats have long occupied a unique cultural space, featuring prominently both at annual Kentucky Derby festivities as well as in the collection of The Metropolitan Museum of Art. After Frank Olive died in 1995, his label continued under the direction of Gabriel Amar.
Mount Mary's Frank Olive collection is currently the largest available online, and the only one featuring anything other than hats.