Fractal models of soil structure have been used to derive models of soil hydraulic properties, which can potentially explain links among soil morphology and soil function. An alternative to these models is to fit widely tested functions to data and optimize their parameters. The disadvantage of the latter approach is that it does not contribute to our understanding of the soil system. Fractal models of soil water retention were proposed more than fifteen years ago and tested by fitting models to data and verifying that the value of the fitting parameter(s) (i.e., a fractal dimension) was within theoretical bounds. Although important as a first step, this approach is not sufficient to fully test the theory. The various proposed fractal models of water retention assume fractal properties of pore-, and/or particle-size distribution, and mass distribution within soil aggregates. The objectives of this work were to: 1) measure water retention properties, particle size distribution, and pore structure from two dimensional images, 2) test two models of soil structure by comparing fractal dimensions of soil structure (as measured under objective 1) with equivalent fractal dimensions obtained by fitting the models to measured water retention. Our results suggest that a single fractal dimension may not be enough to capture the complexity of soil structure. This is particularly true in agricultural soils. New approaches to modeling soil structure and related hydraulic properties will be discussed, with an emphasis on simplicity and applicability.