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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So you’ve cleaned out the closet and gotten rid of everything that doesn’t fit or won’t work or just should never ever be worn in public by anyone ever again, amen. And you’ve made a list, sort of, except that you’re still not sure what exactly you should be putting on every morning when you leave the house because it’s been a long time since you worked in a casual office and you’re still not sure you can pull together a look that is casual and work appropriate at the same time?

How about some suggestions? As you sort through your closet, consider how many of the following you have, and what you might need. Keep your own personal style in mind as you make up your list, but don’t be afraid to try new things on. And don’t ever buy ANYTHING that doesn’t fit your body, your budget, and your lifestyle. Please.

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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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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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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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Stara has a question about suiting:

As you may have noticed (not at all due to my incessant mentioning of this fact), I am an attorney. And I have been informed by an inside contact that I will likely soon be contacted by an ultra conservative employer regarding an interview. For which I honestly need a new suit. The last “interview” suit I bought was nearly 6 years ago, and it is showing it’s age.

My query is this- I am 27. How do I buy an interview suit that is both job appropriate and does not betray my age? I don’t particularly want to plop down $400 on a suit I will never want to wear again. I’m willing to spend a fair amount of cash so long as it is on something I actually like, and not something I feel forced into buying.

I think Stara has exactly the right attitude here: she wants a suit that will make her look professional and competent, but she doesn’t want to go into the interview pretending to be someone she’s not. And she absolutely wants to come out of this with a new job AND a suit that she can actually WEAR to the new job, something that will work with her current closet.

That sounds like a big request, but it’s actually fairly simple, as long as she keeps a few things in mind as she shops.

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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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It’s January, and we’re all starting the New Year by paring down and simplifying and trying to recover from the excess of the holidays. I still have a Christmas tree in my dining room (packed and ready to store, but not yet put away, for whatever reason) and frankly, I’m ready for my house and my life to be completely back to normal.

Although actually a Christmas tree in the dining room isn’t far from normal for me. Sadly.

So instead of putting the holiday decorations in the attic, I’ve been reassessing my closet (of course). I’ve given up shopping for sixty days (11 down! woo!) but more than that I’m thinking about how I will turn 40 in the spring, and how I would like to really streamline my style before then.

I wrote last week about strategies for finding your style; this week, I want to talk about strategies for making your closet workable.

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