Work vs Play: How do you decide?

Since I started working I have often debated over which clothes in my wardrobe should be for work and which should be for play. Every morning I look at my options and ask that question. I've also noticed that this has got worse since I started sewing. For some reason, in my head, there needs to be this distinction. I'm not really sure why, it is just there. Yet the reality is different. I noticed when I reviewed my wardrobe a few months back that a lot of my clothes fall into both camps. 

Obviously there are items that do fall into only one camp. I have an outward facing office job which means I need to look to smart. There is no way that I would wear the short blue lace dress I own or the shorts that I am about to make in the office. Jeans sometimes sneak in (like today, when I can get away with it!). Similarly, I am unlikely to wear the trousers I have for work at the weekends.

However, the majority of my wardrobe falls into both camps. Practically everything I have made has been seen at work unless it was for a specific occasion. This morning I left the house in a rtw jacket (which I dearly love) and while I was waiting for the bus I realised that my Anise would have looked better and yet I'm not sure I want to taint it with the "you've been worn at work" thoughts that circulate every morning.

Perhaps I should just make some items for work. Perhaps I should make more items for home and move some of the loved items to the work camp. Perhaps it doesn't matter at all, and it shows that I have a wardrobe that I love and want to want to wear whatever the situation. It is strange - I don't have the same thoughts about shoes or bags. 

Anyone else have similar thoughts? How do you decide to split your wardrobe? I'd love to know.