Anna, I get this. In my case it's not free time that is the issue -- I don't wear a uniform for a job and theoretically I could wear whatever I wanted for my work days. BUT. Practically speaking, I need to be comfortable, so what I end up wearing ends up being -- essentially -- a uniform. It's a varied and enjoyable uniform, like your commuting looks (except nowhere near as cool!) But it's the same idea -- casual, practical, movable, walkable clothes for the climate and the task at hand, with as much fashion flair as I can muster.
What I REALLY love are the less purely practical occasions -- and I have quite a few -- but they are incredibly varied in nature. From parents' nights at school, to teaching writing classes, to readings in heaven only knows what venue (could be anything from a dive bar to a hip Montreal gallery to the National Library), to theatre outings in the city -- and on and on.
I do try to have quite a lot of crossover items in the wardrobe. But even with those items, I need a variety of other pieces to create good outfits, and even though I have quite a lot of occasions, I end up getting bored if I wear the same thing all the time to each TYPE of occasion. Yet I only have so many of each type. And it feels like a waste to buy stuff that I might only wear twice or three times in a season.
Phew.
I don't know.
In the end, maybe it makes sense to do something like what Lisa did. Figure out how many of each type of occasion you have in a season. And then figure out your personal boredom threshold. If you can't stand wearing the same thing to the opera capsule during a season more than once -- well, so be it. I say, it's your income, your hobby, your enjoyment -- and if you want a new outfit every time, that is okay. After all, you really DO wear the same thing every day to work! So you deserve a little leeway in the off time. OTOH, if you find you can double up, use items in a variety of ways, etc. then that is also a fine thing to do.
