One of my favorite recent purchases is a pair of paper bag shorts. Over the past year, I’ve tried several on but I never committed until I found the perfect pair of denim belted shorts. And in just a few weeks, I’ve realized just how versatile they are! So if you’re wondering how to style them, I’m bringing you five paper bag shorts outfits!

Five Paper Bag Shorts Outfits

I ordered these shorts from Madewell a few weeks back in my typical Madewell size, but was shocked at how snug they were! My recommendation would be to size up one from your Madewell size or stay with your true designer denim size. (Madewell tends to run one size large.) I ended up going up two sizes, and I actually really like the relaxed fit! Keep in mind that I have a very short and straight torso. For those of you with hourglass or pear shapes, definitely stay TTS! 

Tucked Tee + Kimono Outfit 

When I think of paper bag shorts outfits, immediately the first thing that comes to mind is a more fitted tee! With a more fitted, tucked-in top, the shorts are really the star of the show! A bodysuit would also be a perfect option to achieve this look!

Of course, I wanted to take it a step further with a third piece. Adding an additional layer is one of my favorite ways to “complete” an outfit. Although a light jacket would work here, I love the boho vibe of a flowy kimono. The espadrilles make it a bit dressier. To make it more sporty, sneakers would look cute here. Flat slides or lace-up sandals would be a cute option too!

Tee (TTS) | Kimono | Shorts (TTS or size up) | Sandals (size down 1/2) | Earrings 

White Button Down + Paper Bag Shorts Outfit 

For the ultimate classic look, my favorite short sleeve button down is the perfect match for paper bag shorts! Because the top is wider and boxier, tucking it in all around really helps keep definition at the waist and allow the belted waistline to show.

With a classic combination like this, so many shoe options work. I love these nude mules because the really add length to the leg. A white sneaker would be a cute option too, but I could even see this look dressed up with heeled sandals for a night out!

Top (size down) | Shorts (TTS or size up) | Mules (TTS) 

Graphic Tee + Belted Shorts Outfit 

A graphic tee and shorts is pretty much my summertime uniform! But I love how the belted shorts make this look a little more put together than your average denim shorts! You could easily add a light jacket to this look like a utility jacket, denim jacket, or kimono! 

Because this tee is a little more oversized and long, I again tucked it in all-around. Without a full tuck, the tee could look a little more on the sloppy side. If you have more of a cropped tee, I would just front-tuck to bring attention to the belted waist. 

Tee (TTS) | Shorts (TTS or size up) | Sneakers (TTS) | Bag | Earrings 

Sweater Tee + Paper Bag Shorts Outfit 

This isn’t a top I would typically think of for paper bag shorts outfits, but I wanted to try something out of the box, and I love it! It’s a lightweight sweater material with a drape-y fit, and it looks adorable front tucked into the belted shorts.

Although not everyone might have a sweater tee in their wardrobe, it’s a good lesson that tops heavier than a tee or light blouse can work! A lightweight long sleeve sweater would be a great option. Or even sweater tanks like this one I own would work!

I went with an espadrille sandal, but this is another look I could see dressed up with a heeled sandal! Truly any sandal would work with this outfit, depending on the look you’re trying to achieve!

Top (size down) | Shorts (TTS or size up) | Similar Shoes | Similar Bag 

Peasant Top + Belted Shorts Outfit 

Another fun outfit combination is pairing a blousy top like this tie dye peasant top with belted shorts! Depending on the blousiness, you could either front tuck or tuck all around. But again, some tuck is important to keep the belted waistline! This would work with both short sleeve and long sleeve tops. I’m just imagining a summery long sleeve eyelet blouse tucked in these shorts!

The accessories I went with created a fun summery vibe with the woven bag and heeled sandals. And espadrille would be another dressier option. But flat sandals and slides would also look adorable! 

Top (TTS) | Shorts (TTS or size up) | Sandals (TTS) | Bag | Earrings