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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There are a lot of great perks to working from home; this morning, I am counting among them easy access to the leftover Boston Cream Pie my mother-in-law made this weekend. But unlike an office, which often has specific rules about what is and is not appropriate work attire, the home office has no rules. That sounds so great, doesn’t it, until you’re putting on your yoga pants for the umpteenth day in a row and feeling less like a contributing member of society and more like a housekeeper with a laptop.

Working at home is a truly remarkable opportunity, one that most of our mothers didn’t have. Being a WAHM gives you the best of both worlds, and while I would never go so far as to say that working at home is EASIER than going to an office, it certainly has its advantages, like the flexibility to manage sick kids and household chores, and the option to NEVER EVER WEAR PANTY HOSE AGAIN. Thank god.

But once you strip away the panty hose and suits, and add in the housework and kids, what exactly DO you wear to work at home? And how do you keep from falling into the I-don’t-really-need-nice-things trap that seems to come with the virtual office?

Let’s start with this: what do YOU wear when you are working at home? Are you happy with your current work-at-home wardrobe? Why or why not?

On Friday, we’ll talk about what to wear to the virtual office. Hint: there won’t be ANY pantyhose on this list.

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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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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