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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.

Maybe it's just my personal preference (or prejudice) but I think that melrose's suit would have looked better with somewhat narrower trouser legs that were also a little shorter - and which surely would be less inclined to get caught on a shoe. But a smart look nevertheless.

Totally agree with Shyheels. Can't add too much other than I hate it when my pants leg hangs up too. Not because how it looks, actually love look, but it's uncomfortable. Even more so with slings when the hem gets between your foot and shoe. Also heels are made to be seen, as such I buy pants shorter than I used to. Guess I did have something to add. Shyheels just saved me half my typing.

Very presentable - one looks at the photo and sees at first only a well dressed man. The fact that he’s wearing heels is only a secondary observation - one that could easily be overlooked in passing. The heels aren’t hidden, they appear natural and in a way that can go a long way towards normalising the notion of a man in heels. I can imagine the trouble with the pant legs getting caught in the back of the shoes. Ankle boots would indeed be a good idea in those circumstances