For the most part girls look good in whatever they wear, so go with what fits the occasion. I do like a girl who is inclined to wear some kind of heels and a dress.or heels with slacks. I get the impression that the heels help shape the legs, but can't swear to it. It could be the reverse. Girls wear heels who have the legs for them? I know heels are hard on the toes, but slacks and tennis shoes get old, if that's all she ever wears. Boots are nice with short shorts, but only at home. ;-)
Depends on where we are and what we are doing. If she's wearing a dress, I hope that she is wearing high heels. But most of the time I prefer a casual look on girls. I don't pay much attention to the shoes.
Things that guys should care about and don't = Shoes, Purses, Eyeliner, Mascara, jewelry, and fingernails.
I am not a guy but depending on the occasion and the outfit - which ever one looks more appealing is the best way to go. I am a big "flat" freak because they are so comfy and easy under jeans. I wear heels under dresses or dress pants. I am not a big sneeker fan - but I have couple pairs that guys love and also flip flops - definitely under shorts or when its TOO hot outside.
So, to answer your question, Depends on the guy and the occasion. If you are wearing dress pants its more likely that flip flops would turn guys off.
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