Workday Rules: Their Dress Code & Mine

When I first moved from college into the workforce, I worked in a “business casual” office. Their dress code included things like “no sneakers ever” and “no blue jeans except on Friday”.  There were a few instances where I pushed things–wearing black jeans on a Tuesday, for example–and got away with it, and a few instances where I didn’t.  I learned what was allowed and what wasn’t rather quickly.  And I also learned that, largely, it didn’t matter what other people in other departments wore–at that company, it wasn’t any of my business and wasn’t my place to complain or point out other people’s rule-breaking.

I left that company after about 2 years, and my next job was with a company that was very causal. When I started, I wore dress pants and nice tops, mostly with heels.  I worked in the heart of the loop in downtown Chicago and felt obliged to dress nicely.  The company was small, and my particular office housed just 3-4 people depending on what salespeople were in the office on what day.  The other office, based in the ‘burbs, housed about 6 people and was a little more casual–jeans and sneakers were largely the norm.  After seeing my then-boss in jeans, sneakers, and a baseball cap, I became comfortable dressing down.  I started wearing jeans, usually with a nicer top, and heels, and topped with a blazer for a little extra warmth (clearly, the beginning of my style rut).

Nerd Chic
My Nerd Chic set on Polyvore is a good example of what I was wearing when I worked downtown.

When work closed the Chicago office and moved me to the suburban one, it became very easy to dress down. The suburban office was super casual, and the dress code only required that shorts and skirts be longer than 2″ above your knee, you couldn’t wear jeans with holes in them, and that you couldn’t wear shirts with writing on them.  Other than that, pretty much anything was ok to wear… even things I would never have thought appropriate for an office, like hoodies, sweatpants, and flip flops.  Most people wore jeans, sneakers, and casual tops every day, so that’s what I did.  My work “uniform” became jeans, a graphic tee, a vest or blazer, and Chucks, and arm warmers if I was cold (which was most of the time).

At some point, I realized I needed to start dressing a little more adult. It was very likely after my boss sent me a note that said, essentially, “I ask that my sales team dress professionally, and since you’re part of my team too, I’d like to see that of you too.”  Ouch. But, it got me to look at myself in the mirror–I mean really look at myself–and realize that while I was in my late 20’s, I was dressing like an college intern.  I made a conscious decision to change how I dressed at work.

My first rule immediately became, “no sneakers at work”. I did it at my first job, and could certainly do it at my current one.  What’s more, with my shoe collection hovering around 80+ pairs of shoes, even half of that was plenty to allow me to not wear sneakers 5 days a week.  So I cut sneakers out of my work attire “cold turkey”.

As expected, I found it pretty easy to not wear sneakers to the office.  I had plenty of other options, and choosing a nicer shoe often meant I chose nicer pieces to go with it.  It was almost like a 2-for-1 deal on dressing nicer!

But it wasn’t enough for me. I was going through my closet one day and noticed I had a ton of dresses and skirts, and rarely wore them.  I decided to limit the number of times a week I wore blue jeans, and promised myself that I’d wear one skirt or dress a week.  Eventually, that became pretty easy too, and I upped the number of times a week I wore a skirt or dress.

Dress Up
The set Dress Up on Polyvore is a good example of how I started wearing dresses and skirts to work.

I toed the line often, even before putting my own rules in place. I often wore graphic tees that had subtle writing on them–like one that had an entire poem on the back–but I’d cover it up with a scarf, vest, or blazer.  I’d wear shorts and skirts that ended a fair amount above the 2 inches above the knee mark, but made it less obvious by adding dark tights underneath.  I figured, “I’m a young creative, I can get away with it”, and 9 times out of 10, I could and did.

Then I made a fatal flaw. I wore 5″ inseam shorts.  No, it wasn’t just that, though.  In fact, I had worn them numerous times in the month leading up to the incident, but had camouflaged the fact that they were a few inches too short with dark tights underneath.  But one morning, I couldn’t find the cocoa colored tights I wanted, and settled for tan instead.  I wore them with over the knee boots that came up to about where the shorts should have ended.  Big mistake.  Within an hour of my arriving in the office, HR came in and talked to me, telling me I wasn’t going to be sent home, but that I couldn’t wear the shorts to work again.  I tried explaining that I had tights on, but it didn’t matter.

Who Wears Short Shorts?
Who Wears Short Shorts? I did, apparently! This is the outfit I wore that HR didn’t like.

I did raise one question during the discussion with HR. I asked why it was ok for others in the office to show up in sweat pants and cheap flip flops, and yet I couldn’t wear a professional-looking outfit that was neat and clean.  There wasn’t an answer for that, which was frustrating.  I brought it up again later, because it actually really bugged me.  If we were to be presenting, to potential visitors, a professional atmosphere, certainly flip flops and sweats weren’t the way to do that, right?

I did learn from the experience though. Largely, I learned that it doesn’t matter if you’ve worn something before… all it takes is one complaint to do it in.  I also learned not to get too cocky about breaking the rules, and to be more careful when it came to toeing the line between allowed and not.

Since them, work has made 2 changes to the dress code. We are no longer allowed to wear shorts at all, and we are no longer allowed to wear flip flops at all.  I suppose it’s a bitter-sweet victory.  I no longer had to grumble about the lack of professionalism that flip flops that looked like they spent 4 years in a college shower presented, but I also could no longer wear any shorts to work.  But largely, I’m ok with it.  I’ll gladly sacrifice my ability to wear shorts at the office to not have to see someone else’s nasty plastic flip flops!

I’ve also made a few changes to my own dress code since then. I still won’t wear sneakers to work (though I have twice, and it felt very strange), but I’ve started wearing more skirts and dresses.  I have also blatantly asked HR if certain things are ok to wear prior to wearing them.  It’s rare, but I’d rather err on the side of caution instead of having someone else complain.  I pride myself, now, on looking professional even when I do push the limits a little.  I don’t want to ruin that by getting sent home or written up because I’ve worn something I’m not supposed to.

Have you ever struggled with the dress code at work? Tell me about it!

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