When I wear heels with casual skirts, I either feel like A) I look like a hooker or B) I'm too dressy. I usually stick with wedges or flats, but I really love skirts and I really love heels... how do I mix the two?
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... stick 'em down your shirt and make your boobs look bigger!
I am a dedicated heels wearer, with the occasional exception (flips in the summer). For more casual skirts, try a wedge or a shorter, kitten heel maybe (these also look really good with the full skirts that are popular right now). For taller heels, pencil skirts are always good (I assume you are talking about wearing to work?), otherwise I have some slim-cut skirts that go to the knee or just below, and heels look fab with those. HTH
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"Good taste shouldn't have to cost anything extra." - Mickey Drexler
I usually wear kitten heels with skirts, unless the skirt is at least knee-length. I feel like my proportions are off otherwise (it might just be my legs though).
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"We live in an age where unnecessary things are our only necessities." --Oscar Wilde
I think the trick is matching the dressiness (is that a word?) of the heels with the dressiness of the skirt and keeping the skirts knee length or longer. IMO, these would all look great with a cute cotton summer skirt:
Anyway, you catch my drift. Generally, I think that kitten heels, espadrilles, and wedges look cute with casual skirts.
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To be yourself in a world that is constantly trying to make you something else is the greatest accomplishment ~ {Ralph Waldo Emerson}