Eileen O’Connor Weber (June 14, 1918 – December 30, 2012) was a woman who loved the community more than anything. A life-long Briarcliff Manor resident, she was the it-girl of the neighborhood. Growing up in Briarcliff with her mother and two brothers, she was always involved. Whether it was attending masses at St. Theresa’s Church, participating on varsity sports teams, or volunteering with numerous charities, Eileen did everything out of love. She was nicknamed “Sunshine O’Connor” and the name truly fits! She went thorough Briarcliff Manor public schools and graduated from Briarcliff High School in 1936. She studied at Edgewood Park, the college located formerly on the property of the Briarcliff Lodge, and received a degree in Secretarial Science in 1938. She worked for Young & Rubicam in Manhattan for 12 years, and co-opened her own real estate firm, Weber-Tufts Realty, with Betty Tufts in 1954. Her pride for the community took her to many places. In 1974, she was a founding member of the Briarcliff Manor-Scarborough Historical Society. In 1992, Weber-Tufts Realty merged with Houlihan Lawrence, where Eileen continued her practice until retiring at 87. She spent her time volunteering with countless organizations, running the infamous bus tours of Briarcliff Manor, and spending time at Sleepy Hollow Country Club. She passed on December 30th, 2012 at the age of 94. Her spirit will forever remain in the hearts of those she touched personally in the community, as well as all the places that honor her legacy.

Ms. Weber really loved hats. These are just a few in the Briarcliff Manor-Scarborough Historical Society collection. There are more. The captions for each of the photographs provide more information on the individual hats.

Natural colored “straw hat with pink and beige chiffon ribbon and pink artificial flowers covering the hat. Label reads “Christian Dior chapeaux Paris-New York.”

Navy intricately woven pillbox hat. Nicknamed “Jiffy Pop Hat.” Label reads “Amy New York.”
Natural straw boater with red grosgrain ribbon hatband. Label reads “Lee Fifth Avenue.”

Black beaver fur top hat band and black trim on brim. Metal pin and ring attached on brim. Label reads “Scott & Co. Hatters to the Royal Family.”

Black, cream, and gray pleated taffeta turban-style hat with “top knot.” No label.

Cream wool bowler with black velvet hatband and back trim on the brim. Label reads “J. Lily by Eric Javits.”

Red wool hat with grosgrain ribbon hatband. Features several red and black feathers and two artificial nuts. Crown is shaped with a dent. Label reads “Whittail & Shon.”

Headpiece with artificial green leaves, cream flowers, roses and small daisies with faux pearl details. Label reads “The Hat Rack.

Brown wool ‘plush’ felt hat. Hatband of same fabric, fastened with Gucci’s signature symbol. Label reads “Gucci. Made in Italy.”

Natural straw boater with red grosgrain ribbon hatband. Label reads “Lee Fifth Avenue.”

Pink silk “fascinator” with two wire pieces attached on top. Nicknamed “The Martian Hat.” No label.

Karen Smith, Executive Directory of the Briarcliff Manor-Scarborough Historical Society wearing a Red wool hat with black zipper hatband. Black trim on the brim. Label reads “Street smart by Betmar.”

For more information on Ms. Weber see Eileen Weber, a Briarcliff Original on the Briarcliff Manor-Scarborough Historical Society website. The Society also gave permission for these photographs to be taken.

Taken with a Sony A7IV and Rokinon/Samyang AF 24-70 f2.8 FE