A: Short booties are a great look year round, but especially in the transition seasons like fall and spring. I see people wearing their pants wrong with booties all the time and I understand that it can be tricky to know how to cuff them.
You’ll always want to aim to have your pants just skimming the top of the boot. Having them tucked into the boot or over the boot will look funny. If your boot is a few inches taller than mine shown above, then it is definitely appropriate to tuck them in. Most short booties, however, look best when the pants hit point of slightly above the top of the boot.
is there a style question you’d like for me to answer? Post in the comments and I’ll do my best to answer it!