7 Outfit Mistakes My Boss Definitely Used to Notice

No one prepares you for the transition from college to life as an employed adult. Sure, I’d had internships while still in school, but navigating the flow of a 40-hour workweek was an adjustment. One of the most difficult changes? Developing a work wardrobe when for four years I’d relied on not much more than jeans and sweatshirts.

I didn’t have the budget to replace everything and start over, so I had to be strategic: adding a blouse that would dress up my jeans, finding comfortable heels that would work at the office. But, despite my best efforts, looking back now, I can see that I made some mistakes along the way, and while my bosses were never anything but kind and supportive, I’m sure that they noticed the details I didn’t.

Luckily, as I’ve grown into working life, I’ve learned crucial lessons along the way that have helped me better navigate the sometimes confusing world of office dress. Below, I’m highlighting seven dressing mistakes I look back on with regret, but I’m also explaining the changes I made to fix them. While every company has a different dress code, there are still rules that translate whether you’re on the clock in NYC, San Francisco, or somewhere in between. See them all below, then shop pieces to help you dress for your 9-to-5.