Back in high school each night my best friend Jamie and I would methodically plan out our outfits for the next day over the telephone (you know that old land line thing). We both had sisters and each other's closet's to pull pieces from, so in all we had three closet to choose from. Wearing the same top or sweater in the same month was something that rarely happened.
Now I only have one closet to pull from so I have to make sure it's good. So I think about what I know: Season's are predictable, I lived in the Bay area long enough I know the climate by now. And think about what I like: I know in winter and fall I'll want to wear plaids. I'll also want to wear sweaters and boots. So when I buy pieces I know I'll want to wear it allows me to easily update my outfit each new season.
All I did to update this outfit from last year was add new boots and socks. Looking at what pieces I really like and want to wear helps me from mindlessly purchasing items that I won't wear often or won't wear more then one season. It also helps me from having panic moments while looking at my closet and thinking 'what the heck am I going to wear?'. Because you know, I can no longer call Jamie the night before and ask her what tops she has in her closet that I could borrow.