My friend Kristen always says that the best part of freelancing full time is the pants-free dress code at her office. The same can be said for being a stay-home mom; some days, it just makes sense to keep your pajamas on. All day.

These days, though, more and more of us are looking for work, and unfortunately, there don’t seem to be any offices with pants-optional or pajama day attire policies. Which is a shame, because imagine how productive people would be if they just didn’t have to worry about pants!

Sadly, not going to happen.

Job hunting can be stressful (because omg! you have to put pants on!); scoring an interview is both cause for celebration and reason to panic. Because oh my god what are you going to wear???

Don’t panic. I’ve got you covered. Promise.

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Photo via Ann Taylor

Office dress codes can be tricky; while many workplaces have clearly articulated guidelines about what is and is not allowed (no flip flops, jeans on Friday only) there is often a bigger gray area around what’s really appropriate (suit? pants? dressy shorts?). In the corporate casual office, “appropriate” often depends more on what your job is than on any company-wide policy. A good rule of thumb is always to dress for the job you want, rather than the job you have. This means looking at what your supervisor and her peers are wearing to work and taking your cues from them. It can also mean finding a style mentor in your place of business, someone who can give you advice about what’s acceptable for certain functions or situations.

Of course, there are better and worse ways to approach this. Let’s look at an example of how not to handle the the what-to-wear-to-work dilemma.

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Photo via Nordstrom.com

Summer is coming, which means getting dressed for sweltering temperatures outside and freezing conference rooms inside. We all know that you need a cardigan for the office, but how else can you make your summer clothes work-appropriate? You can start by not making these five mistakes.

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Getting dressed for work can be tough — but what if your work day is wearing out your wardrobe? “I teach music classes to children from birth to age 7,” Elizabeth writes. “Every day I am crawling, rolling, running, skipping, bouncing etc. on the carpet with little ones. I’ve been wearing dark jeans and a nice top, but I’m finding that I constantly am wearing holes in the knees! Do you have any suggestions? I want to look professional (I own the business), but practical. I’ve been thinking about going in a ‘fitness instructor’ direction, with yoga pants and tees. I do have a little flab to hide. What do you think?”

I think Elizabeth is on to something.

All That Pant, $59 at Athleta

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One of the most difficult wardrobe transitions you’ll ever make is the post-kids return to work. It’s a tough shift for a lot of reasons: your body has changed, for one thing, and your budget probably has, too. And for many of us, the return to work is a foray into a much more casual office environment than the one we left before the baby came home. All of this often means that our current everyday clothes are too casual, while our old work attire is too dressy — or just the wrong size and shape. And most of us don’t have the cash to start over with an entirely new wardrobe (and of course, if you’re still working to lose that last bit of baby weight, you may not want to buy a bunch of stuff that — hopefully — won’t fit in a year anyway).

So what should you invest in before you kiss the baby goodbye and head back to the office? Ideally, pieces that will work both with your current closet and on their own, and that can transition from work to weekend without missing a beat. Here are my five essentials for the back-to-work closet.

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Admit it: Casual wear can be a nightmare. Dressy events call for a dress, and yoga pants are a perfect go-to for days when you never leave the house, but if you work in a casual Friday office, or work at home, or work schlepping kids to and fro all day, finding the mid point between practical and chic can be overwhelming.

Which explains why so many of us spend our days in those yoga pants.

Casual seems so easy — that perfect balance of actually dressed (rather than possibly still in what you slept in) but not dressed up (an outfit that welcomes sticky post-daycare hugs and kisses). But beyond dark rinse jeans and a pretty top, what is there?

How about a dress and some footless tights? Cute! Chic! Practical!

But wait! you say, I’m too old for footless tights! Maybe, but probably not.
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Well hello there! It’s so nice to be back at The Working Closet! And so fun to be working with Sarah (although it’s a good thing we don’t actually see each other during the work day because my hair is out of control right now).

Spring is in the air (which explains the state of my hair, honestly) and it’s time to put up the winter gear and freshen up your closet for warmer days. Or at least to dream about it while you shovel snow. Either way, it’s fun to think about how you can update your office classics with a few trendy pieces. This spring, there are the usual unwearable trends (MC Hammer called and he WANTS HIS PANTS BACK) and then there are the cute-but-how-do-I-make-it-work trends.

Here’s how!

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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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We’re talking about what to wear when you start a new job, particularly one where the office dress code is casual but professional. Whether you are moving from a corporate environment or from your kitchen table, you will most likely need a few new things to wear to work.

But BEFORE you run to the mall and start buying things willy nilly, let’s talk about how you can make your existing wardrobe work for this new job.

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