Well...in this case it's Sebastian with boots.

What kind of god-forsaken Satan-spawn walks around in hooker boots?! *facepalms*

Sebastian Michaelis

If Ciel saw him doing that, he'd fire Sebby on the spot!

He can’t fire Sebastian. He made a deal with the devil remember? Sebastian stays by Ciel’s side until the time is right to claim his soul.

I forgot...but what would happen if Ciel decided to try on some hooker boots?

I wouldn’t know

I think Ciel would look silly in hooker boots.

He would most likely break his ankles

I've heard high heels are really bad for your back, so maybe he might get bad back pain from walking in those things?

True

Ciel actully wears heels in the anime and manga and they are higher then Elizabeth's.

Or he could just force Sebastian to wear sneakers.