How to Wear the Same Pair of Overalls to Work Every Day for a Week

My favorite outfit when I was a kid was a pair of overalls from Old Navy. They were light blue with flared bottoms, and I thought I was the coolest girl in the world when I wore them. I loved that they were so comfortable, that they were an instant outfit, and that they had tons of pockets where I could hide all my trinkets and treasures. I lived in those overalls until I grew out of them—seriously, I wore them every day unless my mom had stolen them to wash them—but I never forgot about how much I adored them.

Fast-forward 17 years: I’ve found a new pair of overalls that are possibly even better than my flared pair. They’re black denim, slightly baggy, and I usually cuff them to show off my shoe choices. The difference is that while I could throw on a striped T-shirt and go as a seven-year-old, wearing overalls as an adult requires a little more styling finesse. I want them in the mix daily, but it takes a little more planning to wear the same pair of overalls to the office than it does to the playground.

However, I’m never one to shy away from a challenge, and for the entirety of this week, I showed up to work in all my overalls-clad glory. Adding the right accessories and pieces can make the difference between sophistication and sloppiness, and I found that my simple pair of overalls were actually quite versatile, taking me from the office to after-hours. Here, five ways to wear a pair of overalls for the workweek and still look like a grown-up.