True story: My first tech job, my family went all-out helping me prepare. I got lots of free business attire, either handed down or bought as a gift. I had more than enough for my first ‘real’ job. Being someone who actually enjoys dresses and cute tops and blazers, I was in heaven.

Week two into the gig, I was pulled into my manager’s office. “You know you don’t need to dress so nice. You’re on the dev team.”

“It’s okay! I like wearing this stuff!”

“Yeah, but… you look like upper management.”

“…Okay?”

Finally, the truth came out: He wanted me to dress down because I looked like I was dressing ‘above’ my station. I was told to start wearing jeans and t-shirts.

I did so (again, first job), but these days I make a point of dressing up when I go to tech conferences.