Since graduating college, I’ve only had one job that required “business casual” attire. I hated that job, partly because a dead-set-in-her-traditional-ways HR representative made snide comments about my wardrobe everyday (“I wish I wasn’t a professional woman so I could wear jeans!”). It was never “business casual” enough for her.
So for a few years, I rebelled against wearing dresses and skirts solely out of spite. Spending 40 hours a week in cheap polyester because it was all I could afford from the “business casual” area of Target completely turned me off from dressing up for work. Imagine my relief when the job I took at Groupon fresh out of grad school required no change in my wardrobe.
I moved to Chicago and admitted defeat my first winter. It was colder than I had ever been in my entire life. I can say with absolutely certainty that it was the coldest I had ever been because I was born and raised in California and had only visited a cold part of the country once during winter. I lived in leggings, wool tights, hand knit sweaters, and piles of scarves for my first winter in Chicago.
And then spring happened! Glorious, beautiful spring. After spending 4.5 months wearing nearly all black, I decided it was time to break out the bright colors and festive prints. All those dresses that lived in the back of my closet were suddenly now the perfect thing for me to wear. They were no longer horrendous memories of being ridiculed for my sense of style. I embraced wearing dresses. One brave weekend I went through my closet and bagged up all of my Threadless t-shirts and crappy college kid clothes for donating. Very slowly, I started buying new pieces of clothing that were well made, would last for years, were reflective of my style, and were comfortable.
So now I have a closet full of dresses that are reflective of my personal style, which means I wear dresses a lot. I don’t need to. I’m a software engineer (!!!). Most of my co-workers are still wearing their college wardrobes. And that’s totally fine for them!
But I wear dresses. Why? Because they make me happy, and I feel like it’s easier for me to express things about my personality through what I wear than anything else.
I also wear dresses because it’s easier to pick out one thing in the morning than it is to pick out two. A dress is an entire outfit.
Also, somehow, magically, dresses don’t get dirty or dingy as fast as plain old cotton t-shirts. They don’t need washing as often, which is good because they are typically hand wash or dry clean only, likely because their fabric is nicer.
I wear dresses because I don’t have to. It’s a choice that I make for myself everyday to express how I’m feeling with what I wear. Some days I feel like leggings and a hoodie (those days are usually December-March), and other days I feel like 5 inch heels and a floor length dress.