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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Remember going back-to-school shopping? So many options! So few things your mom really thought you needed! SO much angst!

Or was that just me?

Shopping for new ventures — new school year, new job — can be overwhelming, because how do you know what you will REALLY need before you start the new thing? What if all the OTHER girls are wearing skinny jeans and you are wearing boot cut jeans? HOW WILL YOU EVER SURVIVE?

You laugh, but you know it’s true, and it is still true when we talk about shopping for a new job. You don’t want to be the only one in the office who wears a dress (or maybe you do, in which case more power to you! wear that dress! seriously) but you also don’t want to dumb down your style just to fit in. Instead, you want to find pieces that are appropriate for the specific environment of your office AND reflective of your personal style.

Yeah, it’s not any easier now than it was in high school.

No matter what your style or the office culture, there are five things you really ought to have before you head back to work.

Kate Spade Tarrytown - Quinn handheld tote, Nordstrom, $395.00

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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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It’s Monday, and I’m trying to finish my taxes and get the laundry caught up and find my husband’s passport (don’t ask). In other words, I’m having one of those days where I have precisely five minutes to get ready and not a single second after that to do so much as check my lip gloss.

Sound familiar?

Today I have a random assortment of tips and tricks for you, for days just like today, plus some great news about things you can win.

Tips
I learned something interesting recently, about how to find the Perfect Jeans, that pair that makes everyone say, “Have you lost weight?” and “Wow your butt looks FANTASTIC.” And honestly, it’s so simple that it makes me want to cry, because how did I not realize this before?!?

When you are shopping for jeans, look for three things: fit, length and rise. Yes yes, you say, we knew all that — but wait! There’s a strategy here.

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I love jewelry; I love how easy it is to take a basic jeans-and-tee outfit and dress it up with the right pieces. But it is also easy to fall into a rut with your jewelry. Ever notice how every time you get dressed up, you put on the same earrings and necklace?

Next time you go somewhere, try something different. Try adding a pin. You heard me! PIN. Brooch. Something sparkly and shiny and exotic.

It’s easy.

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The jeans-and-tee wardrobe is a staple of moms who spend a majority of their time at home, and with good reason: tees are comfy and machine washable and inexpensive. But tees are also super casual, so much so that it can be hard to feel really professional and smart when you’re sporting one.

Dressing up your jeans and a tee uniform can be as simple as adding a jacket. Putting something with some structure over your tee gives your whole outfit some shape. Go as formal or casual as you like — a suit jacket can do double-duty with a pair of jeans and a tee, while a jean jacket gives your chinos a little edge. The easiest way to up the wow factor of your basic tee and jeans is a trench coat, which is the perfect spring outerwear, but think also about structured sweater jackets, which are a little more flexible than a traditional blazer but can look equally professional and polished.

A jacket is a terrific way to bridge being at home with your kids and being out and about during the work day; take the jacket off to load the dishwasher or make lunches, then toss it on for the school run or a client meeting. Having one piece that has some structure and shape to it gives your outfit a pulled-together look that bridges work and home, but without leaving you feeling like you need two different wardrobes just to get through your day.

Outfits pictured here are all available at Ann Taylor Loft.

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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In the comments on the first post in this series, quite a few of you said that when you are working at home, you still try to look nice, because there is always a chance that you will see people during your work-at-home day. I was impressed by how many of you said, “Of course I get dressed — I have to take my child to school, after all!” Because frankly, carpool moms are frequently the WORST fashion offenders.

Before we get to what you SHOULD be wearing during your WAHM day, let’s run down the list of things you should NOT be wearing:

Sweatpants with elastic at the ankles. Get some yoga pants instead.

Spirit tees. You know the ones, with the school’s name and mascot on them. Buy one for your kid, but not for you. If your child is involved in some kind of extracurricular activity that REQUIRES you to wear the spirit tee, save it for those specific events. And even then, think twice about it.

Battered tennis shoes. Honestly, put some real shoes on. It won’t kill you.

So what is the alternative? Let’s start with pants, shall we?

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