Born into a wealthy family, she entered law school at age 39 and became a radical lawyer with a foot in two worlds.
As an attorney, she worked on behalf of radical labor activists and was a regular activist for the Industrial Workers of the World, involved in the 1911 textile workers' strike in Lowell, Massachusetts and the 1913 Paterson silk strike.
At the same time, she served as the treasurer of the National American Woman Suffrage Association (NAWSA).
Her brother Clarence Ashley was the dean, and under his tenure the school moved to admit women.
Ashley helped force open the clubby world of New York legal practice - both to women as lawyers and to activists with radical politics.