4 Ways to Wear Overalls

Partnership with

Photography by Gabi Wells

Merrick's Art Free People Cross Back Overalls

Outfit Details:

Outfit 1: Free People Overalls, ASOS Ruffle Sleeve Top (similar here + here), Soludos Espadrilles

Outfit 2: Free People Overalls, Sanctuary Top, Cross Sandals, Pink Satchel Bag, Black Bandana Scarf

Outfit 3: Similar Striped Tee, Free People Overalls, Perforated Espadrille Sneakers, Similar Black Leather Jacket 

Outfit 4: Similar SweaterFree People Overalls, Rockport Loafers, Firmoo Glasses (similar pair here)


I’ve been debating about the overall trend for like two years now. I’ve seen them coming back and I just wasn’t sure if I could do it. I wasn’t the most fashionable little girl, and I wore overalls long after they were out, so just the thought of wearing them again brought back some memories of my most awkward years and I wasn’t sure I was interested in re-living those.

But the more I saw them, the more I liked them. Except that I couldn’t find a pair that worked for me until I found this pair. The fitted legs, the cropped length, and the low cross back were the things that sold me. I feel like they’re fun, but a little more grown up than a typical pair of overalls.

Try these four ways to wear overalls!


Merrick's Art Free People Overalls
Merrick's Art Soludos striped espadrilles
Merrick's Art Asos Ruffle Top and Free People Overalls
Merrick's Art Denim Overalls
Merrick's Art Asos Ruffle Top Free People Overalls

For a summery look, I paired the overalls with a bright yellow flutter sleeve tee. It adds a little bit of femininity to the masculinity of the overalls, and then I completed the look with a pop of stripes with these lace up espadrille flats.

Merrick's Art Bandana with Overalls
Merrick's Art Free People Denim Overalls
Merrick's Art Overalls and Slides
Merrick's Art Pink Satchel Bag
Merrick's Art Loose Curls
Merrick's Art Free People Overalls and Bandana

This polka dot blouse is one of my favorites, and it was the perfect lightweight blouse to wear under my overalls. I wanted a little unexpected addition, and the neck scarf was the perfect thing. I finished the look with a pair of simple cross sandals.

Merrick's Art Simple Overalls and Stripes
Merrick's Art Light Wash Overalls
Merrick's Art Cross Back Striped Tee
Merrick's Art Layering with Overalls
Merrick's Art Perforated Sneakers
Merrick's Art Free People Overalls and Striped Old Navy Tee

You guys know I love a good striped tee, and pairing it under my overalls just had to be done. I chose a slim fit tee, and finished the look with some fun, perforated sneakers. I also love that in the cooler months, you can add a jacket right over the top of your overalls!

Merrick's Art Sweater and Overalls
Merrick's Art Firmoo Glasses
Merrick's Art Neutral Overalls Outfit
Merrick's Art Rockport Loafers
Merrick's Art Casual Overalls
Merrick's Art American Eagle Sweater

And the final look is just with a basic sweater and some easy loafers. This look was feeling a little too simple, so I added some dark framed glasses and it all came together.

I think the key with any overalls look is to pair it with sophisticated, feminine pieces. If you pair overalls with a simple tee or tank, keep your shoes more purposeful and age appropriate. If your shoes are simple sandals, add a more sophisticated blouse. Think you can do it??

4 ways to style overalls


  1. Lakenia says:

    I love these looks! I have been looking for age appropriate ways to overalls and you nailed it. What color/wash are your overalls? Thanks.

  2. Susan Stange says:

    I am ALL about the overalls. Haha! They’re especially practical when I go to photo shoots because those pockets are everything! My biggest problem is remembering which pocket I’ve put everything in. Haha!
    Definitely a fan of that striped tee! What size did you get from Boden?

  3. Paige Cassandra Flamm says:

    Those overalls are cute! I’ve been dying for a pair for a couple summers now! I’m totally ordering those ones!


  4. Natali says:

    You’re looking lovely top to bottom in these 4 styles!


  5. Jillbo says:

    “I wore overalls long after they were out, so just the thought of wearing them again brought back some memories of my most awkward years and I wasn’t sure I was interested in re-living those.” THIS IS ME!! Oh my goodness, yes!! I relate!!

  6. Hannahrose Jordan says:

    I love these overalls! Now that I know your glasses are fake, it makes me giggle whenever I see them. Got to say though, they look great!

  7. Liz says:

    Hi! Where is your gray bag from in these photos?

Leave a Reply