I have wanted a pair of overalls for the longest time. Awhile back, I got to borrow a pair to shoot and they were so stinking cute. But I just never pulled the trigger until now.
Alas, I think I may have found the perfect pair of black overalls from Madewell. After seeing them on a handful of other people and thoroughly stalking their website over the past two years, I finally have a pair just for me.




Overalls can be tricky. You don’t want them too tight (at least in my opinion) because they can kind of look, ahem, cheap. I know, I sound like a terrible person writing that. I can’t help it. I’m just trying to keep it real for you and help you with outfit inspo and advice! But you also don’t want them to be baggy. Let’s be honest here, we all remember that Sex and the City episode where Miranda is walking down the street in those awful, terrible, I hope they were burned overalls. In fact, that episode is the single reason why every time I’ve ever uttered, “I want a pair of overalls” in from of Matt he cringes and says, “Yuck.”
I feel like I say this a lot, finding the figurative porridge in the Goldilocks story that’s just right. Sometimes it’s a jumpsuit. Other times it’s a pair of jeans. Today, it’s these black overalls.
The bottoms on these black overalls fit similar to a pair of skinny jeans, but the waistband isn’t so constricting where you feel like you’re just wearing a weird bib over a pair of jeans. That was honestly my biggest concern trying on a pair of skinny jean overalls. But nope! These have a side zipper to close the waist but they are for sure a tad roomier than regular jeans. The back of these overalls, which you can’t tell from the photos (sorry peeps, my bad) has criss-cross straps that extend to the waist, so from a comfort perspective, the back is not restrictive when it comes to sitting, bending over, etc. They also adjust so you can maneuver the buckle to fit whatever length you need for your torso. SIZE NOTE: I usually wear a size 26 (or a size 4) and I took a small.
These are so fun to wear. Style them with whatever you’d wear with any pair of jeans (AKA: an easy closet update that doesn’t require the purchase of a ton of other things). You still have that casual denim vibe, but overalls add a fun twist and keep things feeling fresh.
I wanted this look to be easy but styled. So, I threw on a black and white striped shirt and incorporated some print mixing with this floral bandana. Y’all know I love myself a bandana and now that the holidays are over (I couldn’t find and good holiday bandanas) I’m bringing these back.


Normally I’d go for some Converse sneakers here with my black overalls look, but I really, really wanted to wear my new combat boots. Unfortunately, this exact pair sold out (sad face), but here’s a really similar pair. I also rounded up my favorite shearling boots in this post if these tickled your fancy to get a pair of your own.
To finish, I topped off my look with this insanely soft teddy coat from BB Dakota. I shared it last year in this post and have worn it so much; it’s been one of my go-to pieces that instantly elevate whatever I’m wearing (even jeans and a t-shirt!). It’s still available in different sizes at different retailers, all of which I linked below.