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I think it you keep the top fairly conservative, you would be just fine. I wear that look often. I prefer skirts with heels, no matter the length. Just don't like the body posture/overall look of flats, unless of course, you can carry yourself like a ballet dancer. That said, I also do not like the trashy/short cheap skirt, tiny tank top, 5 inch platform heeled stripper ensemble either.
It's about finding a balance, AND your personal taste and comfort level. Just wear what works for you.
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