“You’re a Fun Dresser!”: How to Own Your Unique Workplace Style

When I started dressing more like myself at work, my boss said four words to me in a team meeting that I’ll never forget: “You’re a fun dresser!”

Benevolent in nature yet backhanded in its delivery, the comment stuck with me. What does “fun” even mean? Like breath of fresh air in the office fun? Or eccentric grandma fun? I was voted “Most Stylish” in high school and damnit, I was not about to be called “fun” without knowing why!

You see, I found myself in a bit of a panic after my first few months sporting 9–5 office attire. I was envious of my friends who wore jeans and sneakers to their quirky startup jobs but still wanted to dress in a manner that shows I work for the nation’s third largest arts center. It was stifling my creativity and, more importantly, my productivity. How had I so quickly abandoned my colorful wardrobe for the solid blouse + printed pants + flats combo every day?

That’s when I decided to get — to use my boss’ word — fun. The two looks shown here fall on opposite ends of my fashion spectrum and are two actual outfits I’ve worn to work in the last year.

I bought this “wild flamingo” pink suit from J. Crew with my first paycheck and it’s still one of my all-time favorite purchases; the tailoring is structured enough to make me feel boardroom-ready but the color and gold buttons keep things playful.

This next outfit was first worn on a Casual Friday when I felt particularly adventurous. The band-tshirt-meets-shiny-skirt look has been all over the ‘Gram this year, and after so many outfit repetitions of it in my personal life, I decided it was time to take it to work.

The gold midi skirt is from Goodwill and was originally about 15 sizes too large; never underestimate the power of an alteration. The Led Zeppelin tshirt was a Buffalo Exchange find and I still wear it about once a week with jeans and Converse sneakers or under blue denim overalls. And don’t worry, you’ll never see me wearing a band tee unless I can name at least five songs. #NoFrauds

When it comes to fashion, I am no stranger to bending institutional rules. Each time, I was anxious to hear what my colleagues and superiors would think about my getup, but the thrill of dressing like myself was too much to pass up. I figured that the more comfortable (relatively speaking) I was in my outfit, the more creative and productive my workday would be.

I was fortunate enough to make it work and to elicit ostensibly positive reactions from others…but how can you own your unique workplace style?

First, know the rules.

Find a copy of your office dress code. No tube tops allowed? That’s fine, you don’t need Glenn from Finance to witness your midday wardrobe malfunction when it rolls down to your midriff. No sequins? Don’t fret — save ’em for your next girls night out and you won’t have to worry about leaving a trail of shiny breadcrumbs around your office suite. Recognize the major NOs from the get go and accept them. After all, there’s a little fun to be had in wardrobe distinctions.

Then, bend the rules.

If you want the drama of sequins without the drama of being called into your boss’ office, consider a metallic midi. It’s flashy, but the modest length gives you leeway. When it comes to consolidating your work-meets-personal-life wardrobe, compromise is key. If it’s the color/texture of an item you love but you know the cut isn’t workplace-friendly, do an image search for clothing with those keywords and discover something reminiscent of your contraband piece yet appropriate for your day job.

And if you’re able, rewrite the rules.

After I began dressing more like “me” at the office, I felt comfortable asking a friend in HR a few questions about the dress code.

Who created it? What department was it designed for? When was it last revised?

All it took was a little digging for me to learn that the rules hadn’t been looked at in 18 years. 18 YEARS!!! That’s 36 NYFWs — even more if we’re looking at the Resort/Cruise/Haute Couture collections.

If I play my cards right, I may be able to contribute to a revised dress code created for this century. I’ll keep you posted.

In the meantime, let me know how you bend (or break) your office attire rules. And check out these badass women fighting to change outdated dress codes at the Capitol last week!

MPD