I know I've become less and less worried about what people think, but that is an almighty hurdle for most of us. My wish to do just whatever I want is tempered with a desire not to embarrass or harm anyone close to me. My wife has known about my love for heels for most of our married life, but until a couple of years ago I hardly ever ventured out in public wearing them.
She will now come out with me when I'm wearing block heeled boots or wedges, and I know I'm very very fortunate in this. However, I believe the biggest problem with most of us is the six inches between the ears. We're worried that everyone is staring at us and laughing at us, and terrified of meeting someone we know.
One of my wife's friends and a couple of others in the same business as me know about my heels and are completely OK with it. I went on the train to a company conference last Saturday in 4.5 inch wedges under a business suit. Seven hours in the train and walking between trains, seven hours at the conference with over 5,000 people present. Loads of people must have seen them, but I got not one comment, not one sign of amusement or disgust, apart from a giggle I heard from a teenager behind me, but even then it might not have been at seeing my heels.
My reason for wearing them, if anyone asks, is that they are a miraculous cure for backache. My back aches if I stand or walk around for more than a few minutes, but heels are an instant cure. I'm not the only one who finds this, as this article shows: http://home.bt.com/lifestyle/four-inch-heels-cure-mans-bad-back-now-he-cant-stop-wearing-them-for-charity-11363970352666
The fact that I absolutely adore wearing them is another matter...
Anyway, that's me. I have about two dozen pairs of heels, from two inch cowboy boots to 7.5 inch stilettos, but recently I've been more and more interested in street heels of at least four inches.