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If I had answered this question on the day it was initially posted (which, incidentally, will be one year on the day after I complete this post) I would have said "Nope!" "Nada!" "Nein!" "Nyet!" etc. This was still in the time when I was wearing heels in private. As of today, however, my answer would be "You bet I am wearing heels!" I see it as a matter of confidence coupled with an utter lack of concern about what others may think and if they should have a problem with it. As noted yesterday, I went to the dentist and it was the first time I was out wearing boots and a skirt while not in the company of someone who knows me. Then in the late afternoon, it was a visit to the (new for me) nurse practitioner, but dressed much more business like in a pair of Aerosoles pumps due to the warmth of that time of day. Today, it was the eye doctor in a pair of ridiculously cute Naturalizer slingbacks. Each and every time I entered the building for these visits, I did so without so much as the slightest sense of hesitation or fear. I marched right up to the desk, and stated my name and appointment time. I did not stop to look around at any of the other individuals who may have given me a second look or felt it necessary to do so. If anyone muttered a negative or disparaging word under his/her breath, giggled, or whatever, I did not notice and more importantly, I did not care. Then, when I got home, I had a bit of a walk from my garage to the front door my place. As today I was carrying my computer bag, bag of my case files, lunch bag, purse, coffee cup, and fumbling for my keys, I thought I had passed by hundreds of people and guess what, I truly did not care if anyone saw me. In fact, I hope some of the women around my complex did as they could sure use some fashion tips! I have progressed to the point where I actually WANT others to see me wearing heels and when I have an appointment, I make sure my heels are fully visible. I can not explain it, but there is a huge RUSH (favorite band, btw) that comes over me knowing that others can physically see my heels. I guess that it comes from always believing that I would never be able wear heels out it public to now, actually doing so. Several weeks ago, I was out grocery shopping while wearing a pair of what pants (trousers for my UK friends) with white Espadrilles. A young man stocking shelves noticed me and then gave me a very obvious second and surprised look. I made nothing of it and went to the next aisle. As I thought about this encounter on the way home, I came to the realization that my approach to such reactions is simple: "I'm queer...deal with it." I have not had to use such a strong approach and I hope that I never will. There are two points that have really helped build confidence - accepting who I am and fully expressing that beyond just wearing heels, such as what clothing I wear, accessories, and the like. I realize that how I approach this may not be for everyone and that's totally cool - I'm completely down with that.

Funny you should ask, I have told my GF of 12 years the exact same thing, "You have it you should flaunt it" She says I leave that up to you! Shes usually a size 4 and 7 shoe, looks incredible in everything, BUT does not want to be the center of attention,,,,,Well I DO! She really wonders how I do it. I will say that my travels back and forth constantly from Chicago to Tampa I am always dressed up. I am in 4- 5" heels 99% of the time with a dress, skirt/shirt, Lulu Align or Groove pants used as dress pants. I did wear on my last trip down a Lulu Align skirt with a Lulu Define jacket and some Nike gym shoes, felt kinda weird to not be in heels but it was a great looking outfit, I thought, even went straight out to dinner when I arrived. We were commenting on boot season earlier and I will be out and about this weekend with a new pair of knee boots or otk boots. I have bought a few pairs of ankle to otk boots already this year. Back to the topic, I love to get an outfit put together and go out for an afternoon or evening. My GF says when it comes to the clothes/outfit and heels I am more of a chick then she is!!! Not sure if that is good or bad but I will take it as a compliment. Most of you know I could care less what people think or say, most people don't even notice. I wear what I like period. I wish it was easier to post pics here but it is a pain in the a**. Come to Chicago and I am sure we can cross paths somewhere! I'm not here for a long time, I am here for a good time!

Forget the end of the year holidays and all that about being the "...most wonderful time of the year" nonsense. This is it - the start of boot season! So, this morning was an appointment with my dentist and this was the outfit I wore (never hurts to make a memorable 1st impression!). Do not get me wrong, I am already looking forward to the return of my warm season heels, but given the choice, I would always select boots over pumps as the former just seems to fit better. Unfortunately, today was just a preview as the weather will warm over the next few days making boots (and tights) a bit "too" warm. And the outfit with the orange skirt was the end of summer clothing day on 9/30.

It’s all boots and jeans for me. I’ve never tried a skirt although I can see the appeal and recognise that boots and skirts are a very nice look. Just not at all sure it would look good on me!

I too like Cat and others here, like to wear skirts and dresses with my heels, shoes or boots. I don't care what others think, I'm very comfortable dressing like I do Happy Heeling, bluejay

Been public for many years and even at work. I'm not even queen as you put it. I love my heels, love how they feel and love how they look. I wear nothing less the 5 inch mostly stilettos yet everyone knows I'm masculine. Women have told me it takes balls, but I'm old enough to remember when if a guy wore an ear ring he was considered queen. Now women have tattoos and brush cuts so why should I not wear heels.

Skinny jean/pants will never be out of date with knee high boots, unless you want to hide the boots

That's exactly the road I have been down for the last 5-7 years--skinnier and shorter pants. Men's suits, at least traditional ones, are not made that way. At some point, I started buying women's pants that were the same color, or at least close to the color of some of my suits. In some cases, you can't tell that I've left the actual suitpants on the hanger at home. In this case, I have nothing that matches well enough, as there are shiny flecks in this fabric. Also, the people who think they know what they're talking about keep telling me, "Skinny jeans/pants look dated! Wide legs are in!" I thought I'd give it a go. I personally think I look better in less expansive clothing. I shall do some more experimenting in the months to come, but somehow I think that maybe I'll land back on skinny, or at least skinny-ish.