Thanks for the shout-out, Maneera! I am honoured and flattered.
As for helpful advice, am not sure I can offer a lot, because I'm definitely a work-in-progress, so to speak. Every year I discover a few more nuances to my own preferences -- and every year, those preferences and needs change a bit along with different weather conditions, a slight change in my work life, different travel needs, different outings with friends. So nothing is fixed in stone.
But here are a few of discoveries that I think hold true for me in my current work-from-home life.
What I need/ want from my clothing inside the home is a bit different from what I want from it outside the home, especially (for me) in winter. That said, there is a ton of overlap. So, when you ask:
When you buy say a T-shirt or a pair of shorts, how do you decide which category it will fall into, especially when all your clothes are comfortable, good quality and fit very well?
..the answer is, I don't really (as a rule) decide what category it will go in. Many, if not most, items cross categories and I could potentially wear them for anything but house cleaning, gardening, or other "dirty" tasks. But the reality is that I have some distinct preferences and tend to wear certain kinds of items in some situations, and others in...well...others.
Indoors for work, comfort and colour flattery rule. In winter this means cozy knits (including cardigans which are easy on/ easy off). In summer, this means shorts and cooler woven fabrics, sleeveless tops in silk or cotton and linen knits. (I don't have air conditioning).
I like to wear colours that make me feel happy. Especially in our long, dark winters. (Shudder).
Outside the home, I really like more structure and often drama in my outfits. So I wear my more tailored items -- blazers and other jackets, for example, when I go out. Sometimes they are the "third piece" that gets added at the last minute before I go out the door -- along with jewellery and footwear and my bag.
I tend to wear knits and cardigans much less in my outside the home life.
Tees and shorts for me are pretty much "at home" wear. I do wear shorts out of the house in summer but will do so mainly if I'm on my way to the gym or going for a walk -- that type of thing. If I have an appointment or meeting, I'll take that opportunity to wear a dressier item, like my sarong shorts (sort of like culottes) or one of my tube skirts.
I do wear jeans both inside and outside. I don't wear them often in summer because it is too hot. In winter they are both at-home and going-out wear for me. I also wear trousers both at-home and going out, but I confess I wear them less often at home.
Does that start to answer the question? Basically, I kept track of what I was actually reaching for each day and made a note of it. I have a sense of the overall proportion of time I spend in each type of activity and try to use that to guide my purchasing decisions -- but I have to admit that I far prefer "smart casual" (i.e. going out wear) to "regular" casual -- so have a tendency to buy more smart casual than (strictly speaking) I probably "need."