Have a million pairs of old jeans that you’re dying to restyle or upcycle? Need a killer pair of high-waisted shorts? Not sure how to wear your cutoffs when you meet the in-laws? Or are you just trying to keep your look simple? Check out these chic ways to style cutoff shorts all summer long. Perhaps you’ll even wear them right into fall.

1. Mademoiselle Embellished Shorts: Jorts are a summer staple. Added bling dresses them up for a more grown-up, modern look. Paired with a neutral top, a bright purse and a turban for the most fashion forward, you’ll be hitting all the clubs in these chic-y shorts. (via Song of Style)

2. Folklore Shorts in White ($45): Add some flair to the traditional, New England-white shorts with a subtle crochet appliqué. The high waist and booty-short fit will accent all the right places, and the white will show off your oh-so-tanned legs.

3. Wild Summer: Style your cutoffs with an oversized sweater and on-point accessories for a perfect summer night romance. You’re sure to be the talk of the barbecue. Your friends will spend the day asking for all the details… and to borrow that hat. (via Sheinside)

4. Ripped Cutoffs With a Bold Tee: The frayed shorts combined with a loud top and flashy accessories equate a sense of “I woke up like dis.” The look is best displayed at brunch, on a weekend getaway to Mexico or while just lounging on the couch. (via Sincerely Jules)

5. Blazer and Shorts: Another way to dress up the shorts is to pair them with a blazer. The white makes this look perfect for the warm season, and the button down is sure to express just how sophisticated you really are. Bonus points for patterned exposed pockets. (via Be Sugar and Spice)

6. Fitted High Waisted Shorts: Go old school with these perfectly fitted, perfectly high shorts. Worn with a faded, unbelievably soft T-shirt, this look will never go out of style. In fact, we bet your mom has an old pair at the back of her closet you could steal. (via Velvet to Vagabond)

7. American Flag Shorts ($58): Feeling patriotic? Grab these custom-made American flag shorts before the Fourth of July to show off your love of your country and your effortlessly toned gams.

8. Slouch in Faded Blue Tone ($159): Sometimes you need to get away from the cheeky shorts and go a little more conservative. We’re thinking boyfriend jeans, just shorter. They’re fabulously comfortable for a moonlit boardwalk stroll.

9. Chambray and Denim: The days of frowning upon jean-on-jean are long gone. A thin chambray top paired with denim shorts looks polished, structured and put together. (via Go Fashion)

10. Moonlight Jade Mom Shorts ($40): High-waisted shorts are all the rage. Mint is all the rage. Combine them for a fresh, casual look. Add some oversized sunnies, and you’ll be ready for your breezy weekend in the Hamptons.

11. Cutoffs With Tights: So maybe you’re not quite ready to reveal your pale stems just yet, or maybe you’re just trying to wear your cutoffs to an evening event. Either way, tights under jorts are no longer exclusively ’90s attire. (via ASOS Fashion Finder)

12. Knee Socks: Transition from day to night by throwing on some knee socks, boots and a big sweater to keep those cool summer nights at bay. Because. There are no summer situations where jean shorts are unacceptable. (via Native Fox)

13. Studded Distressed Denim Shorts ($20): Nothing says music festival like high-waisted shorts and a crop top. Instead of fighting the trend, find yourself a sexy crop top, throw on your best mom shorts and rock out like you mean it.

14. Crochet + Cutoffs: Another festival-cool look, black cutoffs with a simple crochet top and entirely stylish hat will make you look effortless and chic. (via Le Fashion)

15. Heels and Cutoffs: Dress up your fitted cutoffs with pumps, a designer bag and a bright crew neck shirt — perfect for urbane window-gazing or popping in for some dinner at a trendy new restaurant. (via The Native Fox)

16. Faithful Denim Shorts ($50): Throw off the shackles of plain cutoffs and get unique with these sweet floral lace pockets.

17. Cutoffs and Graphic Tee: A graphic tee is a statement about who you are. What do you want your graphic tee paired with rolled jean shorts to say about you? We want ours to say “Love Mean Girls, hate mean girls.” (via Brandy Melville)

18. ’90s Revolution: Now, these aren’t traditional cutoffs, but we’ll forgive them for that. If you weren’t yet sure if the ’90s were back or not, we can assure you they very much are. (via Fashion Vibe)

What is your favorite way to rock cutoff shorts? Let us know in the comments below!

Kelsey Nolan
Kelsey is a word enthusiast, a bottom shelf wine connoisseur and a fierce defender of Los Angeles. When she isn't writing, she is crafting wedding gifts, binge-reading books, and watching poorly written crime shows. Find her handmade crafts at Tiny Burrito Creations and her decidedly witty words at Tiny Fists of Fury.