Although short cowboy boots are chic, stick with a taller option with a narrow leg that won’t bulk up underneath your suit ...

Sock boots are generally stretchy, which can help if you have curvier legs that don’t fit easily into zip-up boots. If your calves are wider, look at DuoBoots or Jilsen for specific leg fits.

Louis Vuitton debuted a pair of ill-fitting boots dyed to mimic a woman’s leg, white ankle socks and a black stiletto. The optical illusion knee-highs, which ring in just under $2,500 in only ...