Building A Work Friendly Wardrobe From Scratch

Earlier in the year (also known as the time this blog dropped off the face of the earth...), I was hired for a normal, go-to-work-everyday-with-other-humans-and-also-interact-with-the-public job for the first time since 2008, when I started freelancing.

I knew I'd love the job, and I do. It requires using a good mix of all my (rather disparate) skills and experience.

There was one small problem. Since I'd started freelancing I'd also gotten married, had a baby, dealt with serious depression/grief bacon eating, and moved a couple of times. I also hadn't really bought any new clothes since about 2008.

Basically? My okay to wear outside of the house wardrobe was down to two pairs of jeans, a few pairs of flats, some scarves, one dress, a skirt, and a few sweaters. Yep, that's it. And my new job didn't allow jeans!

What I didn't want to do was run out and buy a lot of stuff that was merely okay, or bought out of desperation. I'm cheap. And my version of cheap doesn't correspond with buying a lot of cheap stuff that doesn't last, or doesn't really work, or isn't exactly what I want. I guess I'm more frugal than cheap. Or at least that's what I'm telling myself! I need every penny I spend on my wardrobe to really count.

Now that doesn't mean I'm willing or able to shell out major bucks for what I want or need. I'm not/can't. So I need every penny I spend to count. And I don't want a lot of stuff. I want a wardrobe where I really, really like everything in it and where stuff really works well together.

I also know I'm not the only person in this position. College grads, job changers, moms reentering the work force, freelancers rejoining the 9-5 all need to build or rebuild workable work wardrobes. And if you are plus-size it seems even more impossible to build a professional wardrobe that works, is your style, and suits your idea of flattering.

So if you are starting a work wardrobe/starting over, what should you do?

1. Get to Pinning
I started a secret Pinterest board and every time I saw an outfit I really liked or a piece of clothing that inspired lust, I pinned it. (I've since started a new board, and it's public.)

2. What Did You Dress Like As A Kid?
I remember being in the little girl's section of Rich's with my mom when I was about six or seven buying new school clothes. I was frustrating the hell out of the poor woman. See, my mother and my styles have never synched up. I remember she told me that she might as well just sew bands of fabric to the bottoms of my current clothes, because I just wanted to buy the same things over and over.

From ebay. Not my dress, but I'm pretty sure I owned one just like it.

She was right. I did. I went through my childhood very happily in Polly Flinders dresses, simple cardigans, and patent leather Mary Janes. I had a love affair with sun dresses and thick-strapped sandals. I hated sneakers. I was okay with jeans but hated all other pants. Although I loved dresses (and swedish smocking!) I didn't like flounces and fussy details (there's a fantastic picture of my other girl cousins and me at my grandparents' golden anniversary. They are flounced out and I'm wearing a dress that looks like a cream silk blouse tucked into a navy blue velvet skirt. I'd still wear that outfit today if it came in my size. This is a grown-up version. I'm kind of in love. If only it had long sleeves!).

3. What Are Your Favorite Clothing Items You've Ever Owned?
Next I made a list of my favorite clothing items, ever. The perfect black baby doll dress from high school. A floral pencil skirt I wore to rags. My navy blue patent peep toe wedges. A wool plaid skirt from Ann Taylor I wore for years. And a whole lot of other plaid skirts. My first Coach leather bucket bag (it was stolen. I still miss it).

Here's one of my favorite outfits from about six (gah!) years ago.

I'm wearing a navy a-line dress, a gray cashmere flowy cardigan, a polka dot and flowered scarf from Urban Outfitters. A sleek, low ponytail. I'm actually wearing my beloved navy blue wedges. This is pretty representative of how I dressed throughout the mid-to-late aughts.

4. What Do You Need Clothes For?

Work, obviously. But what's the official dress code/how do your coworkers and bosses dress/what do you actually do at your job? In my case, our official dress code is business casual with jeans specifically forbidden. My coworkers wear a pretty wide range of clothing styles.

The biggest limitation is that I work in an administrative-type job at an independent school spread out over a few buildings on hilly land. So heels are out for me. I need shoes I can run around in. Also, because its a school, I tend toward covering up more than I would in another setting.

Don't forget weekends. I want cute, put together looks for running errands, attending the roughly fourteen thousand festivals that take place in my small town, and all the other weekend-type things. I'm going to need a cocktail dress, but I haven't got there yet.

5. Write A List Of Everything You Already Own
It sounds crazy, but it's really necessary. Have you read the 20/20 (twenty wardrobe pieces become twenty outfits) or the 30/30 (thirty pieces become thirty outfits over thirty days) challenges popular around the blogsphere? I highly suggest reading a few. It's amazing how many outfits (with a little ingenuity!) you can wring from a few pieces of clothing. I started work in the spring, and made it through the summer (which is a smidge more casual at my workplace) with four dresses, three skirts, a handful of tanktops, and four summer-weight cardigans/blazers. (Some of these pieces aren't fall friendly. My current work-wardrobe consists of five dresses, four skirts, two long sleeve tops, the same handful of layering tanks, and three cardigans/blazers.)

Now come up with as many outfit combinations as possible. This is great because it gives you a list of ready to go outfits. It's also awesome because it lets you see the holes in your wardrobe. In my case, I really need a black belt and at least two more cardigans. I also need a few more scarves/colorful necklaces.

From Here

For example. I think I'd get a lot of wear out a mustard cardigan. It would look great over my navy dress, gray and white dress, black skirt, brown skirt, and jeans. It looks better on the website than it does here!

6. Analyze and Sum Up Your Style!
Go through everything. What are you pinning? What did you like as a kid? What are your favorite wardrobe pieces/outfits ever? What do you need clothes for? What do you already own/what do you really need?

When I went through my pinterest board I realized I pinned a lot of knee high boots/dark jeans/cardigan/scarf combinations. I also pinned lots of knee high boots/dress/scarf combos. I'm obviously a big fan of the look! The rest of my pins reflected relatively classic looks with retro vintage touches.

From My Color Fashion

This is pretty representative of a lot of my pins. Simple dress, knee high boots. I also discovered I really, really like a mix of browns and blacks.

It's super important that you look at your pins with a realistic eye. A lot of my images feature very svelte, tall bloggers or models with slim hips and chests. I'm short, and am a fat hourglass (chubby with big boobs, big butt. still small waist). A lot of things I love need major tweaking to look right on me.

Looking at my favorite ever pieces helped here. Wrap dresses (or dresses with wrap detail) work well for me. What do your favorite pieces have in common? I really like interesting skirts. I really like cardigans. Dresses make me feel pulled together with minimum effort. I love classic, ladylike pieces. I don't like anything sporty. Et cetera. 

So this is part one of thoughtfully creating a new wardrobe. Have you ever had the chance to start your wardrobe from scratch? What worked for you?