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Estella Warren was discovered by Rhonda Broadbelt Fonte, the owner of Broadbelt & Fonte Models, in 1994 when she was a synchronized swimmer living in Ontario. Broadbelt Fonte then introduced Warren to George Gallier, the owner of American Models. She then came to New York City to shoot some photo tests; during that time Gallier introduced her to fashion photographer Ellen Von Unwerth, who immediately saw Estella's beautifully unique looks and booked her for a photo shoot for Italian Vogue.
Estella is a world class synchronized swimmer, having started swimming with the Canadian national team when she was 12 years old. She was unable to attend the 1996 Atlanta Olympics due to her Cacheral modelling commitment.