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

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

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Monday: My black denim, '90s-style overalls from ASOS ($81) were the foundation for Monday's look (as they would be for the rest of my outfits this week). I paired them with a vintage denim jacket (similar style here), Adidas Superstar sneakers ($80), and a black V neck ($15). A pair of oversize sunnies ($260) and a vintage black bandana ($6) completed my casual look.

Photo: Melissa Medvedich

Tuesday: I took the tomboy feel of my overalls to the next level on Tuesday by wearing menswear-inspired pieces: a striped men's button-down ($97.50), pointy-toe loafers ($89), and a camel coat (similar style here). I added a vintage neck scarf (similar style here) for a playful touch.

Photo: Melissa Medvedich

Wednesday: On Wednesday, I had a jam-packed day and knew I was going to be on the run, so I went with a sportier look that was as comfortable as it was practical. A chunky, oversize sweater (similar style here) provided warmth, and a black wool baseball cap ($24) kept my hair under control. I added a pair of black mules ($119)—they are surprisingly easy to walk in!—to dress it up a bit for the office.

Photo: Melissa Medvedich

Thursday: On Thursday, I had plans to go to a friend's concert at the Bowery after work, so I wanted more of a downtown vibe. I wore my favorite American Apparel black leotard ($29) under my overalls but kept it covered up at work with a vintage bomber jacket (similar styles here), and I finished the look off with my trusty go-to pumps from Zara ($49.90).

Photo: Melissa Medvedich

Friday: Friday fun day! To celebrate the start of the weekend, I wore my favorite jacket of all time— a lavender faux fur from Whistles ($150). To help balance out the funkiness of the jacket, I stuck to a monochromatic look for the rest of my outfit: a black crew neck sweater  ($44.50) and ankle booties (similar style here).

Photo: Melissa Medvedich

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