Dressing for a multi-tasking type of day is not something that I've bothered to muster. From my view there seems to be no way to master this without succumbing to extra clothes, accessories and shoes. Unless you commit your outfit to one phase of the day: which can breed equal discomfort.
Seeing as I've recently taken up working out, I've (started to) overcome the hurdle of wearing my running shoes throughout the day. Once the thought of this was appalling to me. For all you normal folks out there, I know - how can one say no to comfort??? To me this type of comfort does not give you an extra click in your walk. In fact the first time I tried wearing these kicks out I felt supremely paranoid - 30 minutes after I left home I was imagining how lonely my heels and other shoes were, how much better the manly brown leather boots would be.
I can't say that those day's are over. If not for my newly adopted gym encounters, there shoes would probably be in a box, underneath a box.
In order to in short get over myself I paired it will a furry jacket. I will note that I do not know the origin of this jacket, but not in the sense that I don't know where it came from! My mother let me wear it once to a formal event after some pleading ever since I've been mustering the nerve to wear it under the glaring sun. I feel that once people notice that it's fur (faux or real) their curious glances become a) judgmental because who would wear such a jacket out in the day or b) they could care less because they don't care who wears such a jacket in the day.
Never appreciated people who fall into the latter category more! Go on and care less about what other are doing and what you're doing.... *
*If that makes any sense.