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.

MISTAKE: Feeling too stuffy in professional clothes

FIX: Dressing them down with cool basics

For one of my earliest interviews, I remember showing up in a shapeless gray business dress and flats, an ensemble I’d never put together willingly, and it showed. Since then, I’ve learned that there’s an art to pulling off business clothes. Styling them with more fashion-forward pieces is an important part of making them you.

MISTAKE: Not knowing how to pull off athleisure

FIX: Learning the art of high-low

While I know a sweatshirt or casual tee may not work in every office, over time I’ve learned that sporty pieces are a staple in my everyday look. The key is being very picky about which pieces (think tailored) and styling them with more professional items so they don’t feel too casual.

MISTAKE: Considering heels the enemy

FIX: Finding styles that are actually comfortable

After a few too many traumatic experiences with foot-killing heels, I swore them off. Over time, I’ve learned to find value in lower and chunky-heeled styles, finding the fits that work best for my feet instead of swearing them off completely.

MISTAKE: Not knowing the value of a tailor

FIX: Finding a tailor I trust

One of the most underutilized tricks in the fashion game is a good tailor. Almost every time I compliment a co-worker on how amazing a piece looks on her, she mentions the fact that she got it tailored to her body. It instantly adds polish and makes an ensemble feel more put together.

MISTAKE: Wearing jeans too often

FIX: Memorizing go-to non-denim outfits

When in doubt, it’s my habit to always fall back on a pair of jeans, but as years have gone on, I’ve challenged myself to be more adventurous. An easy way to mix things up is to switch one item in a uniform. Go for trousers or a midi skirt instead of denim to mix things up.

MISTAKE: Not investing for the long haul

FIX: Pick and choose forever pieces

For the first few years of employment, it can be hard to find the budget to invest in your wardrobe. But, I wish I’d started being more selective earlier. Picking investment pieces that will last more than a season without falling to pieces actually saves money in the long run.

MISTAKE: Not getting creative enough with what I already own

FIX: Putting together more adventurous outfits the night before

While I admire the women who can mix and match their wardrobe with abandon, I find I’m usually in too much of a rush to style things in unexpected ways. Over time, I’ve tried to put outfits together the night before, and it’s helped give me time to be more creative with my wardrobe.