Dress requirements at my old job were business casual, which basically means a dress shirt and slacks for guys, and whatever the hell a female feels like wearing (short of jeans).
There were three ways that a guy could go with this:
The Spencer Pratt: Last I checked, we were working 100 yards from the NYSE, not going clubbing with the cast of The Hills. You know the type. If you saw one of these guys sweating in the middle of a meeting, it was because they were actively restraining themselves from shouting "Ya Dood!" after anyone finished a sentence (I call this "Jersey Tourette's").
The George Michael Bluth: I hate suits more than anything in this world, but even I wouldn't wear a polo and khaki's to the office. It was like they were leaving to go chaperone an 8th grade dance or something. Even I was never this egregious.
Everyone Else: The standard. Nice shirt, nice pants, nice shoes. Tie and jacket if you're with a client that day. Whatever.
When I transferred up to the firm's Boston office, we had casual Fridays the first week of every month. I got excited. So I showed up the first day with a nice pair of jeans on, a new pair of New Balances, and a Lacoste polo. Nice enough, right?
Wrong. Apparently even though this was casual Friday, you still had to wear dress shoes and tuck in whatever shirt you were wearing. How this makes sense, I have no idea. Their mentality, as with everything else, was "be grateful we're even letting you wear jeans to begin with."
Fast forward a year later, and my new gig obviously has no dress code. Most of us still look decent enough, with collared shirts and nice jeans. I have no problem with a button-down and jeans every once in a while, but how great is it to roll out of bed, throw on a hoodie and a Sox hat and go straight to work?
I know, I know. Lately I've started to push this whole "no dress code" thing to it's outermost limits. For the past few weeks, I've been shaving once a week, and wearing hoodies and hats every day. But who cares? I'm still bathing (for now), and I get all my stuff done. That should be (and now is) all that matters.
Fellow HubSpotter Michelle effectively summed up my new approach to office fashion with the following:
"It's like you're in your Al Gore post-VP phase. He dressed up for years because he had to, and then once he got out he started doing and wearing whatever he wanted. It certainly worked out for him, too. Just look at An Inconvenient Truth and the Nobel Prize he won for it."