From the brief amount of time playing with it, it seems to be rather basic in it's outfit generation.
For example I picked an orange tennis sweater. And it recommended black full zip jacket (to go over the orange tennis sweater? so basically they recommend you not wear a orange tennis sweater?), hot pink trousers and white espadrilles.
So it seems to match color with a random item (hot pink trousers and a black top? and white shoes?). The shoes are also summer shoes, and if you are wearing a sweater with a zip up jacket over top you probably need more then a single ply fabric shoe with rope soles.
Second time it picked a brown fleece jacket to go over your orange sweater, with khaki pants, and light blue tennis sneakers. First why would you ever wear a fleece jacket over top of a tennis sweater, usually tennis sweaters are knit so you are wearing sheep on top of sheep, unless you are playing in -20c probably a bit excessive.
Moral of the story is it seems to be more of a random clothing articles mixed with colour combinations then an actual outfit generator.