skirtsnhose
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I agree that some kind of hosiery is de rigeur with heels. Even in Arizona, I'm always in pantyhose when wearing my heels.
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I've spent months at a time in skirts and heels, and then stopped for years at a time. I just recently went back out again after four years of not going out. Each time I have gone back out after a long break it has gotten easier. This time, it only took me less than 30 seconds of sitting in my car to remind myself that no one cares. I then hopped out of the car and went about my business. The bottom line: just remember the good experiences you had before, and choose to repeat them.