How to Style Skinny Overalls

Overalls are a trend that won’t quit, and for good reason! They are incredibly comfortable and very practical for motherhood. My favorites are the skinny style, specifically the ones from Madewell. The bottom half fits like an amazing pair of skinny jeans, and the cross-back makes them feel modern—definitely not like the overalls you wore back in middle school!

Today I’m sharing several different ways I’ll be wearing my overalls in the coming months—but really, the combinations are endless and I swear these are really, really versatile! In a nutshell: style them the way you’d style skinny jeans!

To skip the post and just go straight to the videos, you can see part 1 and part 2 over on IGTV—just tap on the title to access the links, or come back to this post.

First up, how to style black overalls. Sizing-wise, I normally wear a 26 at Madewell (which is a size smaller than my usual denim size, 27). For the overalls, I tried two sizes and I feel like I’m in between the small and extra small. But after going back and forth about it, the sales gal at Madewell convinced me to stick with the smaller size since these have stretch. Hopefully that helps you figure out what size is best for you!

Overalls / Sleeveless chambray / Jacket / Similar mules (get the original Gucci ones here) / Necklace sold out from my shop

Overalls / White ruffle topSimilar mules (get the original Gucci ones here) / Hoops coming soon to my shop

Same look as above, just with this sweater blazer added!

It’s amazing how much a layer can change up a look! I love this sweater blazer so much—it’s definitely a core part of my #legitmomstyle wardrobe!

Overalls / Similar crop tee / Leopard mules / Hoops coming soon to my shop

Cropped tees are perfect for pairing with these overalls since they don’t have too much fabric to tuck in.

Same look as above, with this cardigan over it.

Once again, just add a layer for a totally different look. This cardigan is under $30 and is a real winner for fall!

Overalls / Similar striped button down /  Similar mules (get the original Gucci ones here) / Hoops coming soon to my shop

Same look as above, with a sweater blazer added on top.

Next up is blue denim overalls. The ones I’m wearing are from 2 years ago, but Madewell currently has an almost identical pair available that I’m linking to below. According to reviews, it has a bit more stretch and fits more like a jegging so you can size down if you’re in doubt. 

OverallsWhite ruffle top / Sandals / Hoops coming soon to my shop

OverallsWhite ruffle top / Mules / Sweater blazer / Hoops coming soon to my shop

Overalls / Black tee / Leopard mules / Hoops coming soon to my shop

Same look as above, with a sweater blazer over it.

Same look as above, with an open cardigan over it. This is a similar one.

Hopefully now you feel a bit less intimidated by overalls and perhaps are ready to take the plunge and add a pair to your wardrobe (if you haven’t already!). As I said, these two pairs are really my favorite style that are available now and I highly recommend them.

Are you into overalls?! How do you usually style yours? Which of the looks I put together was your favorite?

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