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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What’s the secret to perfect jeans? Time, effort, and the right amount of spandex.

Seriously.

Old Navy Flirt jeans, $29.50

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At the beginning of this series, I asked what you all wear to work at home. Selene had this to say:

I’ve been thinking I need a change. I want to step my going out wardrobe up a notch… I’m feeling the need to feel “prettier” than just my standard same-ole jeans and t-shirt type of thing. I actually had my first hair cut in months yesterday (YIKES!) and am feeling good! I’ve been putting myself second for so long (probably since I had my daughter 2 years ago and she became #1, LOL)

I get up so early in the morning though (4am) that I can’t see getting up even earlier (3:30am) to shower and look nice just to pad on over to the office 20 feet away.

BUT, it would be nice to maybe use my current “out” wardrobe (jeans) at home, and get something nicer for when we go out.

I think we all know what Selene is talking about; at some point, we’ve been so focused on our kids that we have lost sight of ourselves; we stop getting haircuts (I once went almost an ENTIRE YEAR without a cut), we stop buying clothes, we stop getting dressed for anything that’s not a special occasion. It’s inevitable, I think, but it’s not necessarily desirable. And it’s easy to change.

Jeans are a fine wardrobing piece for a day at home, whether you’re working for pay or working for love. What you put on TOP of the jeans, though, can make a huge difference in both your look and your attitude. The key is to find tops that are more stylish than a basic tee but are ALSO machine washable AND affordable.

Thank god for Old Navy.

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Hello, and welcome to Part Three of what may very well be a never ending series on suits! Which will be useful come fall when the Casual Friday look is replaced by the sheath dress and her cousin, the suit.

I can’t tell you how happy that makes me.

Stara started this whole thing with a question about what kind of suit to buy for a job interview, specifically an interview for a fairly conservative office; she also asked what she might wear UNDER the suit. She specifically wanted options that were NOT a button front shirt, and I have to agree that the button up shirt, while always appropriate, isn’t very exciting.

So let’s talk about what the other options are!

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I love e-mail. This week, I had a great e-mail from Amy:

I recently found out I’m pregnant with my second child and upon hauling out all my maternity clothes, I realized how long it’s been - stylewise - since I had my daughter three years ago.

I also realized how cheap most maternity clothes are. Many of the items were pilled and/or have shrunk to the point of not fitting, even now when I am at about 10.5 weeks.

Another issue is that I am showing already a little, with my regular clothes being tight already. I have invested in some great belly bands from Blush, but often you can see the button on my jeans through the band.

I stay home now, working as a writer, but I still want to look put together. Dressing well, if casually, helps me feel professional when I am writing or conducting interviews.

Might you be willing to advise on these issues? Such as where to get good quality maternity staples, etc? Also, might you be willing to ask your readers at Friday Style if they would participate in The Maternity Closet? I would be thrilled to kick it off!

Congratulations, Amy! Babies are the best.

Because Amy is not going to work in an office, she doesn’t need to worry about finding suits, but she DOES want to invest in a few basic pieces that will both get her through her pregnancy and keep her looking great as she — and the baby — grow.

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I know that I said I would tell you what to wear to the office holiday party, and I PROMISE we’re going to get to that, but first I have something Even More Exciting for you.

A contest! Yes, another one!

The Working Closet Flickr pool is still going strong, which makes me incredibly happy; it’s so fun to see what you all are wearing every day, or every so often. And occasionally, you show us what your adorable kids are wearing too, which is even MORE fun because kids are cute and they have great clothes.

And so we’re going to give your KIDS a chance to win a prize this month. Just for being their stylish selves.

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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.