I bought a couple pair of really tall socks, in the hopes of wearing them with a denim skirt and my brown boots. One pair is light blue with a cream colored lace ruffle--not real lace, but kind of like lace that was made with a thicker thread--if that makes sense. The other pair are cream cable knit knee high socks.

Since I live in MA--and it's pretty chilly here right now--will I look silly walking around with bare legs between the tops of my socks and the bottom of my skirt? (probably 4 inches of flesh?) How high do I wear the socks? I'm thinking just peeking over the tops of the boots--but not sure if I should go up to my knee cap?? Any other ides or suggestions? Or am I too old for this look? (I'll be 40 this month--though I feel like I'm 25.)