9 Fun & Fabulous Ways to Dress Up Shorts (PHOTOS)

Adriana Velez | May 28, 2014 Beauty & Style

stylish shortsIt's hot and you want to wear shorts. But you also want to dress up. Well hello 21st-century gal, you're in luck -- because you can do both. There are dozens of ways to dress up shorts and make them go from casual/day-in-the-park to perfect for date night or even (depending on your office culture) work. It's all in how you put your separates together, and it's easier than you think. So have a look at some of our favorite dressed-up shorts looks and think about what you've already got in your wardrobe that you could recombine for a polished but cool summer.

stylish shorts pin


  • With Knee-High Socks & Matching Hat


    With those pins Taylor Swift makes sure to wear shorts all the freakin' time, but she always gets it right. Here's an especially cute look with knee-high socks, high-heeled oxfords, and a cute felt hat to match her socks. Then just to bring home the point that these are her fa-a-a-ancy shorts, she's got a grown lady purse on her arm. It's a very polished but youthful look.

  • With Pleats and Pumps


    Look, pleated shorts! Are these making a comeback? If they're being styled this way, I might be okay with them. The length makes these more office-appropriate, as do the belt and shoes. And then the bow-tie blouse makes it even better.

  • With a Buttoned-Up Blouse


    You don't even have to wear "nice" shorts for a going-out look. These are just denim shorts. But a crisp, white blouse buttoned all the way to the top plus that smart fedora elevate these short-jorts. By the way, ladies? We need to wear hats more often.

  • In a Bold Print With Bright Blouse



    I love these chevron-printed, cuffed shorts -- especially with the bright blouse. This would be fun for a date.

  • Shiny Shorts, Baby!


    Are you up for this? Kate Hudson is rocking these satin hot pants with the long, cozy sweater. I like how her sleeves dangle past her fingers -- and the hem of those shorts. Exaggerated lengths keep you from looking stuffy, not that Kate has ever in her life looked stuffy. If this is too wee for you, I think a longer pair would still work for an evening out.

  • With Ultra-Long Cardigan and Bow


    Another example of exaggerated, contrasting lengths -- little shorts with a maxi-cardi. I like how she's tied her blouse at the waist to make a sort of bow belt (almost), and how her satin bag matches the blouse.

  • With a Blazer


    ($59.50, J.Crew) This look is so J.Crew ... and that's because it's right out of their catalog. I could be wrong, but I think they invented the blazer-with-shorts look. And I love it. For summer, a white blazer with shorts in a white-accented print looks sharp.

  • With a Blazer AND an Oversized Striped Top


    Here's Chrissy Teigen working the blazer/shorts look again, only instead of a t-shirt, she's got an oversized striped pullover. A "suit" (or even just jacket and shorts in the same color) looks so put-together, don't you think?

  • Black & White


    This is another super-simple look: Elegant black shorts with a white eyelet blouse. Pretty! And with that bold, red lipstick, it all looks effortlessly chic.