(My) Most Wonderful Time of the Year!

[Gige]

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. 

Edited October 2 by Gige
Typo

[Shyheels]

Always a fan of boot season myself - I have the early year boot season which runs from 1 Jan to 30 June Annette late year boot season which runs from 1 July to 31 December.

But colder weather certainly does bring out the pleasure in wearing knee and OTK boots 

[CAT]

BOOT SESAON IS THE ONLY SEASON I CELEBRATE !!!!!!!!!!!!!!!!!!!!!!!!

[Cali]

October is our hot season. It is in the 90's here today on the beach. So, if I went to work today, it might be shorts and knee highs. But it's errands day, so I wore shorts and Steve Madden mules.

I now have 7 knee high boots: faux suede, suede, and leather; block heels and stilettos.

But why wait till fall, knee highs and shorts is a great summer look too.

[Shyheels]

It’s always skinny jeans with me. If I lived where it was really hot I might go with looser jeans or chinos and ankle boots. I wear shorts only for cycling. 

[mlroseplant]

The problem with the beginning of boot season is that it coincides with the end of motorbike season. I really need to dig out my knee highs and check their condition. As I recall from last late winter, I suspected one of the shanks was beginning to get weak on my favorite pair.

[Gige]

Allow me to ask a question but before I do, I want to make it clear that I am not attempting to disparage, insult, or otherwise comment on any member of this community. That which I ask is only relative to me. My question is if it seems to be arrogant to, as I say, "If you have it, flaunt it!" My wife has always told me that I have great legs and as the picture with the orange miniskirt shows, I believe that yes, I can totally rock it out! Although I always had great legs, my mid-section needed work - a lot of work. I recently have dropped a substantial amount of weight from my stomach area and it is starting to show. Thus, my clothing sizes are smaller (and I am hellbent on not going up one size ever again). So, as I see it, if I can rock out a miniskirt where/when appropriate to do so, why  shouldn't I do it. Again, when and where appropriate to do so. 

@CAT Throw your answer in here as I am sure you do so!

Edited October 4 by Gige
Added content

[CAT]

11 minutes ago, Gige said:

Allow me to ask a question but before I do, I want to make it clear that I am not attempting to disparage, insult, or otherwise comment on any member of this community. That which I ask is only relative to me. My question is if it seems to be arrogant to, as I say, "If you have it, flaunt it!" My wife has always told me that I have great legs and as the picture with the orange miniskirt shows, I believe that yes, I can totally rock it out! Although I always had great legs, my mid-section needed work - a lot of work. I recently have dropped a substantial amount of weight from my stomach area and it is starting to show. Thus, my clothing sizes are smaller (and I am hellbent on not going up one size ever again). So, as I see it, if I can rock out a miniskirt where/when appropriate to do so, why  shouldn't I do it. Again, when and where appropriate to do so. 

@CAT Throw your answer in here as I am sure you do so!

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! 

[mlroseplant]

There is sometimes a fine line between confidence and arrogance. However, I don't think the simple act of wearing a skirt, even a short-ish one, comes close to the line, much less crosses it. Congratulations on the weight loss.

[bluejay]

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

[Shyheels]

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!