Like Cindy, I love wearing high heels, but I find as I get older that I cannot take the really high ones any longer. When I transitioned previously I had this pair of open toe pumps with a 5.5" heel that i loved to wear out but only in the evenings with girl friends or clubbing.
Mind those clubbin years seem an age ago. These days I have found that I can get the height by wearing wedges without the discomfort. My tallest wedge is a 4" inch, but generally my heels these days are 2" or 2.5"
I am 5'7" tall so this means I don't look too tall even in heels.
One thing to remember though is to make sure your legs are hair fee if wearing a shooter dress or skirt. I never shave my legs only get them waxed at the beauty salon. A good full leg wax and bikini line wax keeps me hair free for about 28 days. I also moistureise my legs and thighs daily to keep them looking good even today. Also dont forget to wear ultra sheer stockings or panty house - preferably 10 denier.
One interesting little gem I discovered is that Marks &Spencer in the UK have a very nice line of 10 denier open toe panty hose that look absolutely great with well manicured and painted toenails with a open toe sandal or high heel pump.
In fact looking at my JudithLynn wardrobe I have about 26 pairs of shoes with only 4 pairs of flats. I also like to wear high heel boots especially in winter. When working in the UK as JudithLynn I always wore my high heel boots to work changing into high heel pumps (3") at the office. Of course walking in high heels has its advantages as it gives ones hips a natural sway.
Hugs
