Cracking the Business Casual Code

When I moved to San Francisco and entered the start-up culture, I thought things couldn't get better – especially when it came to my "uniform." Jeans and a cute top? Check. A bold lip with fun nail colors? Yes, please.

So, what is business casual and how can we follow it in a respectful and fashionable way so that HR doesn't have to sit down with us about the appropriateness of our outfits? We may be millennials and we may like to wear jeans but can still have our ish together in the office. Here are some simple tips I've learned the hard way.

Don’t take advantage of the casual dress code

As much as millennials get a bad rap, I have to say our business casual office desires are not crazy. I was selling high-end tech over the phone. I wasn't facing the customer so why did I need to dress like it? Because some old white man wore a tie to work every day of his life?

But as my sales territory changed, and as I had to be at work at six a.m. and on at that time too, business casual slowly morphed into leggings with a tunic (on a good day). Eventually, my hair was in a top knot every day. I no longer tried to hide the bags under my eyes with makeup. I fell into the very trap traditionalists and baby boomers worry over whenever they hear the words "business casual" or even worse – gasp – "casual" dress codes. I'm ashamed to say I even wore athleisure.

Don't get too casual like I did.

Err on the conservative side

In an office in Downtown Chicago, we were asked to dressed professionally but with the exception of Fridays. I was told by someone in HR that Casual Fridays were nightmares for them because more conversations were had than the rest of the week. She guessed it was because the lines were blurry. Just because someone else is showing a certain amount of skin doesn't mean that I, knowing what I know now, would call their bluff. Instead, I would play it safe.

It also just has to be said: It's easier for men. On Fridays, they wore jeans and a button up and called it a day while the rest of the week involved a tie and slacks. It's not so easy for women. Is this hemline too short? Are sandals all right? (I have been told yes, when it comes to work casual, as long as they aren't flip flops, for the record.)

Understand where you work

Casual in a California start-up was much different than casual in downtown Chicago. That's just the reality of it. In the former, I was never facing the client. I did see clients sometimes in Chicago. This also informs how we dress. In California, the majority of the staff were also millennials. In Chicago, I worked with every generation, from people on the verge of retirement to recent college grads.

I don't want to be judged by what I wear and it isn't fair for anyone to do so. A baby boomer would tell me – a millennial – that life isn't fair. For me, it just means, fair or not, I'm also not willing to wear whatever the hell I want in protest resulting in a sit down with HR.

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