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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Yesterday we talked about strategies for getting dressed for a new job; let’s talk today about what to actually WEAR. I have three suggestions, each tailored for a different type of office dress code (get it? TAILORED?!? I’m so funny).

Option one: No suits, but no jeans either
Many offices have relaxed the rules about suits but have NOT embraced full business casual, for what I think are obvious reasons. If your new job is one of these offices, consider mixing and matching your existing suit pieces with more casual but still tailored separates. Pair the skirt or trousers from your suit with a twin set or blouse; wear a sheath dress with a cardigan and ballet flats. Keep your look simple and professional, and keep the lines tailored and clean.

Option two: Jeans, but no shorts
This is the typical business casual office, the one where the men come in every day in khakis and a golf shirt. This is actually my favorite kind of office, because it allows you to dress up or down (and by DRESS DOWN I do NOT mean either yoga pants or flip flops). Wear your suit jacket with mid-rise, dark rinse jeans and great shoes, or the skirt from your suit with a really lovely t-shirt or crew neck sweater and flats. Don’t toss your suits just because the office is casual; mix and match them with your more casual pieces.

Option three: Anything goes
This is the hardest office to dress for, honestly, because the temptation to show up in your shorts and a t-shirt will be almost overwhelming. But I really believe that no matter WHAT your coworkers are wearing, you owe it to yourself to put a little effort into your outfit. Pair your jeans (dark rinse! mid rise!) with a cool graphic tee and bright driving mocs, or wear a funky cotton skirt and a cardigan. Be creative with your outfits, but don’t just toss on whatever it was you wore to work in the garden the day before. And for god’s sake put some real shoes on — save the flip flops for the weekend.

Coming Friday: what to buy, and how to budget for it.

Congratulations! You have a new job! New things are always fun, because change brings challenges and opportunities. But change is also scary because what on earth do you WEAR to the new job?!?

Moving from one office to another — or from your kitchen table to an office — can be daunting for a lot of reasons, not the least of which is the whole idea of what’s appropriate attire for your new work environment. You don’t want to overdress, but you certainly don’t want to UNDERdress, and either way you want to make a good first impression on your new coworkers.

And all that is before you even start doing the work you are getting paid to do.

So what DO you wear to a new job? Do you dress up, dress down, try to wear what everyone else is wearing?

A little bit of all of those, actually.

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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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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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One of the hardest parts of working from home is balancing the working part and the home part. And — let’s face it — it’s the home part that makes it hard. During a normal work-at-home day, we not only do the work that pays the bills, we also clean and cook and sort laundry and hug sticky children. And we sit on the floor an awful lot, and sometimes even venture outside.

That is a lot to get dressed for.

Most of the time, moms default to dressing for the messiest possible kid thing. I see moms all the time who look like they are ready to fingerpaint with a hyperactive toddler — they are wearing worn out sweatpants and stained tee shirts, as though they are just waiting to have something disgusting wiped on them. And while motherhood is often about the wiping of the disgusting substances, you don’t have to turn yourself into a walking Kleenex. In fact, I wish you wouldn’t.

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