So, I have a bit of a dicey question. How much do you spend on clothes? Or on shoes? I’ve been inspired by your columns and am starting to upgrade my wardrobe, but it seems to involve such major investments of cash. I don’t have thousands to spend- I might not even have hundreds to spend during one season. I’m just not sure what the range of reasonable is.

I love this question, because it gets right to the heart of what I believe about having a really functional wardrobe — a working closet, if you will. Having the right clothes isn’t about how much you spend, it’s about how you shop, but shopping costs money, and in this economy, having a strategy for your spending is crucial.

I am hesitant to put a dollar amount on my shopping, or to say that I spend X each month or year. I don’t have a specific shopping budget, nor do I track what I have spent. Instead, I constantly assess and reassess my closet, looking to see what is and isn’t working, and I don’t buy anything that I can’t easily incorporate into my current closet. I keep a running list of pieces I could really use (honestly, I only rarely NEED anything, but there are always gaps) and I shop off that list.

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A ridiculously long time ago, I had the following lovely email from Kristen:

I’m 30 years old with 4 yo boy/girl twins. I stayed home with them until they started preschool in August of last year. Now I have a flexible job where I work the same hours that they’re in school. My job is really casual i.e. jeans and sweaters are just fine. When I wore slacks, white blouse and a sweater vest one day, my boss wanted to know if I had an interview somewhere! I’m at a community development not-for-profit organization so I generally work/meet with people in similar offices and dress codes. Personally, I would prefer to spruce up a little more, but am met with comments *all day long* when I do so I just tone it down: dark jeans, button-down, thin knit sweater and a pretty necklace.

I recently bought a lovely pair of dark olive green driving mocs. They have a bit of sheen to them although I wouldn’t exactly say they’re patent. They have the treads on the bottom which lends a more casual feel. When I bought them, I envisioned wearing them with everything: khakis, jeans, etc. My problem? SOCKS! Color? Texture? I’m really sad because I haven’t worn my shoes at all yet. Trouser socks seem too insubstantial and slippery, but I don’t know about cotton crew socks. Both brown and black socks just look wrong to me with the beautiful green color.

Kristen, I hope those shoes haven’t been sitting the closet all this time, because they sound fantastic.

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I love handbags; I love them even more than I love shoes, if that is possible. A bag is a terrific place to test out bold color or texture. A bag is an easy, and inexpensive, way to change your entire look. And no matter how much bean dip you ate during the holidays, your bag still fits come January.

Work It, Mom! loves bags, too, and they have paired up with the lovely people at CareerBags.com to give one lucky winner a BRAND NEW bag, suitable for work and weekends. To enter, join the Career Bags group at Work It, Mom! and upload a photo of your bag.

Complete rules and all the Fine Print can be found here.

Come for the contest, stay for the contents of my handbag!

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I’ve spent a lot of time over the past two weeks getting my sons ready for their first day of school (which is TOMORROW, don’t hate me please). This year, my seven-year-old will wear a uniform for the first time, so his closet is currently neatly hung with white polo shirts and navy chinos and shorts. He also has to wear a dress shirt and tie to Mass on Thursdays, which is simultaneously the cutest thing EVER and a little bit heartbreaking.

My baby! In a TIE! Thank god it’s a clip on.

Back-to-school shopping was always one of my favorite things as a child, and even now, the start of school gets me thinking about what I need for my own fall closet. This fall, I am coveting a few things: a swingy trapeze jacket, an everyday black dress, and a bright cheery tote. But before I bring any of those things home, I need to clean out my closet and assess what I already have. I try to adhere to a strict one in, one (or two) out policy, both to keep my clothes from overwhelming me and to prevent my wardrobe from looking dated.

So this week, after the kids go back to school, I will be emptying the closet and trying everything on. And photographing it for your entertainment.

Which brings me to The Working Closet Flickr pool. Starting September 1, I challenge you (yes, all of you! including you in the back there) to share photos of what you are wearing every day. Or every weekday or work day or every day that you can find the camera and get someone to take your picture. Tell us whatever seems relevant about your outfit–where you got it, why you chose it, what you like (or don’t like) about it. Photograph your clothes on you or on the hanger; shoot your entire outfit or just a specific item or detail. Share as much or as little of YOUR working closet as you like.

Jacket and jeans from Old Navy, blouse from J. Crew.

The rationale is simple: seeing what other women are wearing to work (even if your office doubles as your kitchen table and your boss is still wearing diapers or napping every day) can inspire our own wardrobe choices. Fashion magazines are a wonderful source of information, but only if you’re planning to replace your entire closet every season. Seeing what other working moms are doing with that black skirt from five years ago and the ubiquitous jean jacket can actually be far more useful.

I promise to post a photo every day in September; after all, as a freelance writer, every day is pretty much a work day for me. Take some time in the next couple of weeks and get your closet ready. And then, for one month, show us what you’re wearing to work. And yes, I mean YOU in the back. Come on–you know you want to.