Not all boot styles go well with all dresses. Creating contrast between boot and dress styles can make a boring outfit look more interesting. The wrong type of contrast, however, can make your outfit look clashy, and not in a good way. For example, thick, chunky booties won't look good...
A great, cozy, fall look might include a pair of skinny, ankle-length jeans and a cream-colored, cable-knit sweater. For something more elegant, try a black cocktail dress with simple gold jewelry and a red or black clutch purse. 3 Pair leopard print booties with dresses or skinny pants...