Hmmm. I have 2 pairs of uggs, the black presidios, the ultra tall chestnuts, and a really cute pair of "LOVE" brand sheepskin booties in pink that I bought from T.J. Maxx for @29.99 over the summer. Being in California, (and yes, it does get cold enough here to wear them!), I have worn all of my sheepskin boots with cropped denim. I don't like to wear them under regular jeans, they seem too plain, and you can't even see them! I usually wear them with cropped denim jeans, and anything on top, a tank, polo, hoodie, ski vest, denim jacket, and whatever I do, I always make sure that my clothing is fairly fitted, to balance out the puffiness of the boots. I also like to wear a scarf with uggs, just to balance out the look. I hope this helps you! Oh, and btw, I haven't the nerve to wear them with a skirt at all.