Perhaps you could start out building your data model using an existing language? That'd give you the chance to experiment with the semantics, and figure out wh

Perhaps you could start out building your data model using an existing language? That'd give you the chance to experiment with the semantics, and figure out what you need to express in your DSL in a fairly rigorous way. Once you've nailed that, you could start playing with syntaxes that could be compiled to that data model. Some sort of declarations and then expressions for "outfits", maybe? Have you considered using Prolog? I'm no expert, but that was my first thought for tackling this kind of problem.