Every summer I feel like shorts need to prove their place in any woman’s wardrobe.  Few women really want to wear shorts.  They’re basically horrible.  However, when the temperature gets to a point where you can fry an egg on the asphalt, there is a strong possibility that they will get worn.  Shorts are like the vegetables of the clothing world.

So what does fashion do this summer?  They put out a terribly unappealing shorts shape with hopes that someone will bite.  They’re called paper bag shorts, which basically means they have a higher waist and a gathered waistband with a belt.  Oh great.  Just what women want, to have to tuck in their tops and to have excess fabric around their hips.  Yea, thanks, fashion.

On the other hand, however, I look at paper bag shorts and think, well maybe they are a good answer.  After all, the more relaxed shape almost makes them look like a skirt with leg holes.  This could be good for range of motion than a skirt while not being as clingy as shorts.  What can I say?  I guess the jury is out on these.

Five Ways to Style Paper Bag Shorts

That said, if you love them or hate them, paper bag shorts come with quite a few caveats which I am going to advise on below as I showcase some outfits using them.  And if you want more option, don’t forget to check out the additional paper bag shorts at the end of the post.  For the five looks, I am using this olive pair from Nordstrom.

Outfit #1

paper bag shorts

As the rises of pants and shorts have gotten higher (meaning the waist sits higher on the waist), shirts have gotten shorter.  This is why you’re seeing so many cropped (or what appear to be cropped in comparison to what used to be out there) tops in the store.  When wearing paper bag shorts that have so many details in the waist area, not mucking up that area with a top that is too long is important.

This is why I styled this first outfit with a cropped t-shirt from TopShop.  This style is short enough that it doesn’t require tucking but won’t lay over the pleats or tie on the shorts.  I finished the outfit with a pair of nude wedge sandals from Sofft, a raffia tote and scarf from Chan Luu.

Don’t like the look of your legs?  Try wearing a pair of shoes that closely match your skin tone.  A longer, leaner leg line is created.

Outfit #2

paper bag shorts

If you want to wear paper bag shorts, you better be prepared to tuck in your tops.  There is no point in having all that activity in the waist area if it isn’t visible.  Plus, can you imagine how lumpy and bumpy you would look if you didn’t tuck in your tops?  No thanks.

What I do like about the idea of these shorts is they can look dressier than most shorts styles out there.  That said, I styled this pair in a dressier manner using this top from Nic + Zoe, a pair of block heel sandals in cognac from Lucky Brand, Bauble Bar triple strand necklace and orange handbag from Marc Jacobs.

Outfit #3

paper bag shorts

Paper bag shorts aren’t just for dressy shorts looks.  It’s all in how you style them.  In this outfit I created a more casual ensemble using this red and white striped t-shirt, navy Superga sneakers and nylon backpack from Rebecca Minkoff.  I finished the outfit with earrings from Treasure & Bond.

Just remember to tuck that t-shirt in.  If your t-shirt is short enough, you can let it delicately pool at the waist without tucking.  Another tip to keep in mind is how pleated or gathered these shorts are.  Pleats and gathers can work if the pleats aren’t too deep or the gathers too full.  The goal with these shorts isn’t to look like a human balloon.

Outfit #4

paper bag shorts

If you have some relaxed tops that aren’t too long, you can try tucking them in to your paper bag shorts.  Just make sure the tops aren’t too long or too relaxed so they don’t look too blousy when you tuck.  I styled this Joie top with the paper bag shorts and finished the outfit with a pair of orange wedges from MICHAEL Michael Kors, a navy cross body from Tory Burch and mint green earrings from Kendra Scott.

If full shorts make you feel squat, try wearing them with heels.  I’m not talking spindly stilettos (unless that is your jam), but even a small heel will make a difference in mitigating the squatness that can be created with shorts with wide leg openings.

Outfit #5

paper bag shorts

This last look shows a way to wear a more relaxed topper over a pair of paper bag shorts.  The cardigan creates a more relaxed drape while the shape of the waist is still visible.  I styled these shorts with a basic cotton tank from Nic + Zoe, a kimono style cardigan from Cupcakes and Cashmere and finished the outfit with flat sandals from Sam Edelman, an olive bag from Sole Society and statement necklace from Kenneth Jay Lane.

Shop for Paper Bag Shorts

Shopping for paper bag shorts?  Check out these additional styles.