As those of you who are hanging out at The Working Closet Flickr pool know, October is “Does this work?” month; we’re all digging around in our closets for things we’re ambivalent about and asking the Internet to help us decide what to do. So far, I’ve given away a shirt I never wore and I’m following up on some terrific recommendations for jeans.

I love Flickr.

As you may ALSO know, I gave up shopping for the entire month of September; I didn’t buy a single pair of shoes or article of clothing or handbag, just a new refrigerator and a full Cub Scout uniform for my son. I learned all kinds of things about myself from my thirty day shopping fast (not surprisingly, I often shop when I am bored! and stressed! because new shoes will solve whatever problem I am facing! or not! it’s hard to tell!), but I learned even more about how to know when your wardrobe is and isn’t working.

And now I will share that newfound wisdom with you. You’re welcome.

I think very few of us shop out of any real necessity, and when we do, it’s typically a panicked, oh-my-god-I-need-a-dress-RIGHT-NOW kind of thing. And thus we wind up with racks of clothes we never wear or just don’t love. The first step, of course, is to assess what you really wear; to do this, keep a Fashion Diary, for two weeks (or longer, if possible). The simplest way to do this is to photograph your outfits every day (hello, Flickr pool!) and make notes of what you did or where you went. At the end of each day, ask yourself if the outfit worked. Were you comfortable? Confident? Were you able to go about your business without worrying about your cleavage spilling out or your pants falling off? Or did you spend the day with your trench coat on because you realized after you had left the house that your blouse was completely see through?

Any piece that is a complete disaster for an entire day goes in a “maybe” pile. Can it be salvaged, with tailoring or laundering or layering? Try wearing it one more time; if you still feel uncomfortable, get rid of it.

After two weeks, step back and look at the big picture. Are there things you wear all the time? Are there pieces you always get compliments on? Are there pieces that consistently made you feel polished and pretty and professional? Those should be the core pieces of your closet. Make sure they are in good condition; if they need repair or even replacement, take care of it. For basics like tees or tanks or jeans, consider buying multiples; that way, you will ALWAYS have a fantastic pair of jeans to throw on for Casual Friday.

Take time as well to assess the failures: what were the functions or events that you struggled to get dressed for? I have a terrible time on the weekends, with my kids’ soccer games. I don’t really do shorts, but my usual Casual Mom Uniform of capri pants or a cute skirt just isn’t cutting it on days when I have to herd five-year-olds or when the weather is still hovering near 90 and there is nary a shady spot in sight.

NOW go shopping. Stock up on what works, attend to what doesn’t. Buy what you will REALLY wear. And then stop shopping again, for another two weeks, and do the whole thing over. Thoughtful shopping insures that you have what you really need when you walk into the closet; careful assessment of what you’re wearing, and how it is working, gives you confidence that you really ARE putting together a functional wardrobe.