hmmm sometimes I guess....yes.
I learnt a long time ago that just cos fashions were current, didn't mean that they had to be worn, and wearing what I loved made me feel more comfortable, and therefore more of me came out IYKWIM?
In relation to physical stuff yes I think it does. The wrinkles starting for form around my eyes (despite years of good face clean/moist/high SPF) show that I like to smile and laugh, my sometimes crazy curls definitely reflect me, yet sometimes they are sleek and polished, my eyes are green and a bit different, just like me.

Yes I'm comfortable in the way I look, but it was a looong loong time coming. I'm comfortable with me, the whole me, and the way I project is a part of that. Like you MD I often wonder though if what comes across as perceived by me, is what others see too though.