I'm really enjoying all the responses and different angles from which folks are coming at this.
I should add that right now my discomfort has absolutely nothing to do with uniforms or job dress codes, as I'm unemployed in FL. It is purely a byproduct of lifestyle and climate. Goes to show constraints come in many flavors lol.
I'd love to wear some of my more fun shoes more often, but the biking/walking makes it prohibitive. I have tried narrowing that gap some by no longer buying a heel over 3" but still, there are shoes that you can get about in and those for really walking. Ditto some of my nicer clothes, and especially dresses. The environment (hot) and environmental norms (very casual) are at play here. But it would be nice to not have the heat dictate so much - no sleeves, no toppers for interest, what fabrics breathe better. C'est la vie!
I think I have narrowed the gap in the stay home wear and gym/workout gear. I do feel good in those items. And since I wear them at least 75% of the time, good thing!

A great question. I run into this issue often on weekends when I am doing lots of walking and I want to wear an outfit with a shoe or sandal, but a sock with a sneaker is a must for heavy walking and my fussy feet. It doesn't matter how comfy the shoe is, or what insert or goo I put on my feet, if I am walking for lots of miles, a walking sneaker and a sock, and only those two, are the solution. This means my outfit must be centered around the sneaker and often I want to wear something else that would not require a gear style shoe. I can try to find ways around it, but ultimately, the activity and not my mood of the day, will dictate my footwear and outfit options.

I run into the same issue at work, I want to wear my dresses more often, but I'm just too cold to do so. I can put on a cardigan, or a blazer, but that doesn't help my exposed legs. Sitting with a blanket over my legs is no fun, and I'm not going to wear hose in the summer and look weird to others. So I just don't wear dresses to work.

Over time I have tried to keep these issues in mind and purchase less dresses and more comfy and low heeled footwear but these adaptations only go so far. My only solution has been to try and wear the items I want to wear, when I can, and purchase few of them since I rarely sport them. And purchase the items I will wear more often. Practicality is a big player in my wardrobe management.

I have been contemplating the possible (but unlikely) family reunion in Jamaica at the end of this year. What I'd wear. The lifestyle and climate really changes things. Changes them so much, you *do* wonder if you're still you. What does dark and spooky Quirky Waif do in the Land of Sugar Cane and White Rum? I mean, you definitely don't hang around in neon light reflected off of subway tile with running mascara. The best Quirky Waif can do is go for surreal... stand around on the veranda, look out the iron work, and hope a strange goat with soulful eyes will wander into the picture frame...

Mosephina, this is such a good thread! First, let me say that in your situation it totally stinks that you have all these great clothes but you are stranded with only your two feet or two wheels as transport. And that your little community cannot appreciate you for the style maven that you truly are. I have had a tiny taste of this when my husband takes our shared car to the airport and parks it there while he's flying for four lo-o-o-o-ong days. We are such an auto-centric nation, and our neighborhoods are not set up for pedestrian living the way other countries are (and a few of our walkable cities). I feel your pain and your heat, and I think you're pretty darn brave and optimistic--seeking solutions to your puzzle in positive and creative ways.

I sometimes wish I was able to wear the clothes I want to wear, even though I could technically wear anything I wanted, I live in a very dressed-down vacation/resort community (in winter). In the summer, everyone is just trying to make it past the scorching parking lot and into the cold A/C. I wish I could go bare-legged indoors, but it's just too cold. Hubs and I were talking about relocating to a warm place with more even temps and less A/C (one can always dream, right?). It would be nice to live in an area where people dressed up to go out for dinner, or at least didn't do a shocked double take when I did. I think dressing is part of lifestyle, and most people take it into account when considering a job change or relocation. They might not think about it consciously, but I think it's part of deciding if they want to live in the city, country, or suburbs or what have you.