I'm not gonna lie to you: I think boots with shorts is a terrible look.
(Actually, I think the whole shorts-instead-of-pants-or-a-skirt is ridiculous, since I think shorts are reserved for hot summer days when traveling or throwing on over your bathing suit at the beach, but I digress.)
Shorts + boots/booties/furry abominations AKA Uggs = FUGLY.
I realize that many of you would like an explanation of my disgust, to which I must respond: tough noogies. My venom for such a juvenile, trashy, sloppy look is deep-rooted and irrational. I cannot express it clearly.*
I will say the following by (lousy) way of explanation:
1. It reminds me of something vaguely athletic, and we know how inappropriate that is when not on a field, court, or track. Please see Exhibit A:
2. It reminds me of the revolting Southern-California-Girl-Bullshit that inspires people to do this:
3. Basically, this "Sloppy and Wishing I Was Still 16 So I Could Get Away With It" look says it all for me:
To sum up, do everyone a favor and wear some pants or a skirt (one that covers your arse, preferably) when wearing your boots. Believe me, you and everyone with eyes will be glad you did.
*And no, adding tights under your shorts and boots does not change anything.