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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We’ve been talking about how to build an office-friendly wardrobe that will also work for those hours and days when you are NOT at the office. The goal, of course, is to have a closet full of basics that you can mix and match and wear for years to come. The place to start any wardrobe overhaul is by assessing your existing wardrobe, which includes making a list of pieces that you are missing.

As you go through your closet and try on everything that has survived the purge (pieces that fit AND are in good condition AND are classic enough not to reflect a specific trend or moment that has long passed), you need to take note of what you DON’T have. While you might easily identify gaps in your basic pieces — no trench coat, for example, or no office-appropriate jeans — you also need to think about the details: Do you have the right undergarments for every piece in your closet? The right shoes for every outfit? The right accessories for every look?

That fabulous white shirt won’t look so fabulous if you’re wearing it with a green bra, trust me. Or even with a white bra that shows RIGHT through.

Make two lists as you clean your closet: one list of Big Pieces (trousers, skirts, blouses, dresses) and a second list of Foundations and Accessories (lingerie, jewelry, bags, shoes). These are the things you need to shop for, because these are the things you actually NEED. Nothing else, at least for right now.

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This week, the Wall Street Journal had an interesting piece on the pitfalls of business casual attire. And it’s a big pit, this Casual Friday dress code; one image consultant referred to it as “the black hole of style.” Employees are often confused about what precisely is appropriate for the Casual Friday office, and they wind up wearing the wrong thing more often than not.

The WSJ points out that the rules of business casual often vary dramatically from place to place:

Consider the progress of Neonu Jewell, export compliance counsel with Accenture in Chicago. At a Fortune 500 hospitality company where she used to work, a dress code barred denim — so some people wore sweats. At her next job at a Washington law firm, senior attorneys were disapproving of women who wore open-toed shoes on summer Fridays. At Accenture, 37-year-old Ms. Jewell says, business casual still involves suits or at least carefully maintained slacks, shirts and blouses, which she says reflects the highly professional work environment there.

That bit about people wearing sweats to the office of a Fortune 500 company made me die a little inside. Seriously.

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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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Not all bodies are created equal — some girls, for example, get the curves, while some girls don’t. And of course, as with all things about our bodies, we typically pine for what we don’t have (curly haired girls want straight hair, and vice versa) instead of working with — and appreciating — what we have.

Fashion media focuses on skinny girls — the models, even for plus-sized clothing, are wee little things without hips or breasts. But most women are not twee stick figures; real women come fully equipped with breasts and hips and thighs, and translating fashion trends from one extreme to the other can be tricky. The secret is not to start with the trends, but with your own shape. Rather than trying to smash your curvy self into skinny jeans and a tank top, learn to make fashion choices that make the most of what you have.

Today: Five basic tips for dressing your curvy best.

Photo courtesy of Lane Bryant

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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 love handbags. I could stop shopping completely if it weren’t for handbags. I have wee little evening bags and gigantic tote bags; I have bags in suede and leather and canvas and nylon and silk. I have an exquisite beaded bag, and a crazy Vera Bradley paisley bag.

I love bags.

The secret to a really successful handbag, especially for the office, is to choose one that can hold all your stuff AND that is the right size and shape for YOUR size and shape.

Let’s start with the stuff that needs to go inside.

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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.