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How to Adult: Dressing for work

hooters uniform
so pantyhose

My first couple of jobs were in restaurants. Then retail. Then more restaurants. Then gyms. All of these jobs came with mostly hideous uniforms. Seriously hideous. So many oversized polos and button up shirts with ties. So much khaki. So many strange smells. So much discomfort. Really, I think my Hooters uniform was the one I hated the least. And not because of the distinctly 80’s style (scrunch socks holler) but because it was the only uniform that was supposed to make me feel happy in my own skin. Flaunt it!

I then transitioned into the world of gray cubicle walls and branded pencil holders. This world came with its own uniform: business casual. In the past eight years I have been in only one office that was anything less than business casual, and since that office was mostly college-aged girls, we often wore yoga pants at least two days a week. Yoga Pants Office was years ago and during my time in the business casual world I struggled with how to meet the dress code and express myself.


I failed. A lot. I always felt frumpy. I never felt comfortable. Lots of money spent on my NY & Co. credit card for boring ass clothes that I can never get back (although let’s get real, their sweaters and cardigans are perfection). And when I tried to step outside of a typical business casual ensemble into something with more personality, I felt awkward at best. I think pencil skirts are supposed to be cute. I have one that is not flattering. At all. If you thought that was impossible, you were wrong. Frumpy pencil skirt is a thing. I found it.

The only time I felt like I was making headway with my business casual dress code was when my boss at a government project gave me the green light on dying my hair pink and purple. “Yes! I get to be myself!” I thought. Then my hair dye faded and I cut it all off for charity and it was back to square one. And it still didn’t solve my frumpy-attire problem anyway. I cool hair and a super not cool wardrobe to match (I’m so complex).

Until I found the job I have now. I work in marketing for a tech startup in DC. My job is challenging and rewarding, and after two months I still haven’t had a boring day yet.

And there’s no dress code.

I mean, I’m sure if I showed up in a “Go KKK!” tee or a Frederick’s of Hollywood teddy then my boss might sit me down for a chat. But outside of the kind of outfits no one should wear in public anyway, we’re free to be whoever we want to be. After accepting the job I counted down the days from government contracting business casual to tech startup do-what-I-want attire. I eyed my jeans with anticipation. I’m certain my Vans flats were smiling at me.

There’s only one problem. I don’t know how to adult.

I’ve tried doing the jeans and a tee thing at work and it doesn’t quite fit. I might be in the minority, but I want to dress my age (most of the time). I want to dress in a way that says “Hey, I’m professional and also very smart and also super important but also I am fun and nice and happy to help.” Picking out that outfit everyday has proven harder than I expected.

I tried to put together some hip outfits. Like my black/gray monochrome ensembles, my short skirt with baggy sweater. They felt good. But they still didn’t fit. They felt like great outfits for a weekend movie with my husband or brunch with my girlfriends. I love the shabby chic look. The messy hippie thing. It’s comfortable and I love the aesthetic but it doesn’t feel like it fits at work.

I’m surrounded by people in jeans and t-shirts but I’m coming to the realization that just isn’t me.

now we’re getting somewhere

I’ve felt the most comfortable at work in my more polished outfits. Not quite business casual but not quite weekend casual either. Skinny jeans, flats, and a button-up shirt. A tee underneath a blazer. These are the outfits that make me feel good. These are the outfits that make me feel like myself at work and while strolling through the streets of DC. I need more of these outfits.

I need to embrace that I’m not the cool, jeans and a tee at work kind of girl.

Not most days anyway. Most days I want a little bit more. Most days I want to be a little more put together. More feminine and more fashionable. And I’m not alone. The two other ladies on the marketing team are more polished than jeans and tees most days too. Maybe it’s a marketing thing…

Only two months into freedom, I’m still figuring my style out but it’s getting better every day. I’m figuring out what outfits make me feel just as frumpy and tried as business casual and what outfits make me feel like a million bucks (and ready to kick some digital marketing ass).

Maybe it’s the almost-30-year-old part of me, or the marketer part of me, or the never-taken-seriously-in-corporate-settings part of me… or maybe it’s all of those and more. Whatever the catalyst, I’m eager to spend some time figuring out what my personal style is as an adult.

I’ve divided my Pinterest fashion board into one casual and one upgraded board to help guide my style as I get comfortable with my clothes-personality. And I plan on documenting my favorite outfits for a while so I can really look back and see what makes me feel good.

Things that make me feel good: being “put together.”

Things that make me feel like sleeping: jeans and a hoodie.

Now it’s time to get fashionable.

Or to try really hard anyway.

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