Maximizing the pieces in your wardrobe means wearing everything with everything else. But eventually, you will come to a point where you can’t possibly pair two things — a print blouse, say, and a different print skirt. Or CAN you?

Blouse available at Talbots

I love the idea of mixing prints; it gives depth and visual interest to an outfit. But you can’t mix things willy-nilly; you need to have a strategy, otherwise you will look like your kindergartener. Or MY kindergartener (he’s not the snappiest dresser).

When you think about mixing prints, think about three things: color, scale and style.
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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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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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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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Charlene wants to know about what to wear on a business trip:

I do at least one business trip a year and I always struggle with what to take and how not to take too much stuff. The company I work for is very casual so I like to look professional but maintain the casual feel. Also, keep in mind with what I do I have to wear a closed toe shoe at all times.

There are three simple strategies for packing, no matter where you are going.

Pack only things that you REALLY wear. A business trip is not the time to test out a new skirt or jacket; you want clothes that you will be comfortable and confident in.

Pack basic pieces. Think both in terms of shape and color; neutral pieces in classic shapes are your best bet (black pencil skirt, brown wool trousers).

Pack pieces that work together. Choose one color palette for your trip, to guarantee that the things you pack will do multiple duty. Neutral basics plus a pop of color, in a blouse or sweater, keep your look fresh and flexible.

MICHAEL Michael Kors trench coat, Nordstrom, $128.00

So what actually goes in the suitcase?
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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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Is there anything better than the work conference, the kind that takes place somewhere cool and includes social functions like cocktails or dinner? It’s kind of like a vacation, but without the kids!

But it’s NOT a vacation, and you should not pack the same things you would pack for a vacation. This is work, and you need to dress like you are working.

Even for cocktails and dinner.

Ann Taylor Loft V-neck contrast stitch dress, $69.00
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I was recently telling my neighbor about my whole socks-are-against-my-religion thing (on a day when the temperature dropped I swear to you TEN DEGREES while we stood in her driveway) and she was coming up with all sorts of great solutions for me (because I was wearing a dress and no tights and was moaning about how COLD I was) (although in my defense the temperature went from the low 60s to the low 30s in about three hours that day so bare legs were SORT OF appropriate, for a little while at least).

Where was I? Oh right — what to wear if you don’t want to wear socks.
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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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