I wear my boots on the outside of my pants all the time. The last time I wore my Jessica Simpson stilettoes shoe shopping, the shoe manager told me she had the same pair, but had to give them away when her feet grow during pregancy. Mine are not "modest" heels, most 4 inch + whatever platforms. I get the eye roll, more often from older adult women. The eye roll is where they see your boots, roll their eyes up and see you're male, then roll their eyes down to look at the boots again. By that time I am past them Kids sometimes will point it out to their parents. Rarely a comment.
My boots are real or faux leather or suede. I would guess the responce might be different if I wore a fetish or shiny plastic looking boots. Or boots covered in sequins.
It took sometime to start wearing them on the outside. But my boots weren't cheap, so why hide them. I trying to expand my boots into other colors and styles, like the western boots in ICE from Freebird.