How I’m Styling Overalls for Spring

Overalls are all the rage this spring. I wanted a pair, but I hadn’t worn overalls since like the 6th grade. Everyone I saw looked so cute in them, but I was still hesitant.

Since I wasn’t fully committed, I didn’t want to invest a ton of money. I found a pair at Target that seemed like they would fit the bill: the inseam wasn’t too long and the leg wasn’t too wide. They were like Goldilocks’ overalls.

Now, I have to confess something. They sat in my closet for almost a month before I wore them. Maybe I was waiting for the right time? Eh. Maybe I was just a little scared to actually wear them.

When I finally pulled them out this last week, I loved them! Why did I wait so long? One quick tweak though–they inseam was still a little too long. They had a raw hem anyway, so I ended up cutting off about an inch so they hit at a more flattering point on my ankle. Voila! We were in business. The longer I wore them, the more ideas I had on how to style them.

My exact overalls are sold out, but here is a very similar pair that are actually cheaper than the ones from Target! I think the key to wearing overalls and still feeling put together is twofold: choose a pair with a slimmer leg, and the shirt underneath should be fairly fitted to avoid bulk.

Look 1: Layered

I tried a high neck tank underneath, and threw on this open knit cardigan from Target for an extra layer. The sweater hits at my hips, so the proportions are still balanced. My accessories are always pretty simple, so I added my Birkenstocks with the big buckle for a little something extra. You could definitely wear this outfit for a park day or school pick up/drop offs.

Cardigan (I sized up one) / Similar cardigan / Similar tank / Birkenstocks

Look 2: Stripes

I love a good stripe, it’s just so classic and versatile. The tee is also fitted, so I don’t have to keep tucking it in on the sides. Because the t-shirt is very casual, I wanted the shoes to be too. These Gola sneaker mules definitely have that vibe, plus are fun for the warmer temps–the look of a sneaker, but the feel of a Birkenstock clog. Perfection. This is an easy every day outfit option for overalls (I mean it’s basically like you’re wearing jeans and your favorite t-shirt)–comfortable, put together, but not fancy.

Striped tee (tts) / Mule sneakers (tts)

Look 3: Cozy casual

Just because we have a string of really warm days here in Chicago doesn’t always mean spring is here to stay. To keep the outfit feeling like spring, but still warm enough for the Chicago temps, I chose a long sleeve v-neck bodysuit. I liked that switching up the neckline gave the outfit a little different look, and that the sleeves were still fitted. To keep my feet cozy, I put on my Birkenstock shearling clogs (I’ll be living in these on those chilly spring days). Just like two others above, this is also an easy every day look for play dates, the library, or running errands.

Similar bodysuit (tts) / Birkenstock clogs

Look 4: Feminine Blouse & Clogs

In general, I love pairing an item with feminine details with more structured or menswear pieces. So the last look I wanted to try had to have a ruffle. Enter this top from J. Crew Factory–the ruffle was present, but not overpowering. The pattern blended well and added a little dimension to the outfit. Because I chose a more elevated top, I threw on my clogs for a little extra heel. The shape and style of the clogs matched well with the general look of the overalls. While may be this isn’t practical for every day, this outfit would be perfect for brunch or a casual date.

Similar top / Similar top / Similar clogs (tts)

I’m really not sure why I waited so long to try these overalls. They’ve become a closet staple, and for such a great price! There are countless ways to style them, and you don’t feel like you should be heading to the farm.

When you venture out on your own to look, keep in mind how the bottom half will fit–straight leg crop ? Skinny leg? Regardless of what style you actually choose, just make sure it hits at that sweet spot on your ankle: right at or above your ankle bone.

Don’t be afraid to try pops of color and experiment with different tops and layers, too!


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

About Me

Hi! I’m Cassie I originally started this account as a way to answer the question, “Twins! How do you do it?!” but those twins I mentioned are starting pre-school in the fall, so I’ll have some free time. A former teacher, I have always loved clothes, putting outfits together, finding a good deal, and picking up style tips. Now that the world is my oyster with this newfound freedom, I’m feeling an urge to explore my creativity in that area. I hope you’ll follow along, and invite your friends!


%d bloggers like this: