I can't remember if it was here that I read that one of five ways to look modern is to appear like your outfit was just "thrown on" - a little rumpled or askew or untucked. Well, this is my M.O. and always has been, so yay for that!
Then I came across this Pinterest link on how to wear jeans with different boot styles, and realized the messy half-tuck with ankle boots may be the solution to my dilemma of weather (can't show skin) vs. style (need to look current).
It's part of a four part series and I found the visuals helpful. Perhaps many of you do this already? It is officially going into my bag o" tricks!