Nominal failure pressure of ice decreases as the size of the contact area increases, over a wide range of scales. In this paper, the new and emerging concepts of fractals have been introduced to the problem of modeling this ice mechanics phenomenon. Models have been developed to explore effects of progressive failure with local load redistribution and uneven contact geometry. Unlike the nonsimultaneous failure models proposed to date for ice mechanics, the present progressive failure models show size effect in both mean and extreme ice failure pressures. While the present progressive failure models assume uniform contact, a separate fractal model of uneven contact geometry has also been proposed. This model provides a qualitative explanation for the size effect over the full range of scales.