What To Wear Jean Shorts With This Summer, From Brunch To Date Night

There's nothing easier to throw on in the summer than a pair of jean shorts. There are so, so many ways to style your denim shorts: whether it's with a bathing suit after the beach, with a bunch of flash tattoos at a music festiva, or with a clunky pair of boots for an afternoon hike, they work for pretty much any time and any place. They're comfortable, go with everything, and only get cuter the more they stretch out. Plus, you don't really need to wash them that often (jumping in the ocean with them on counts as the same thing as a spin cycle, right?)

There are so many different kinds of jean shorts, though, it's often hard to decide which are appropriate for different situations. Should you wear your shredded white cutoffs to the office? Or your stiff black bermudas to the beach? As easy to wear as jean shorts are, there are certain styles that work better for day versus night, and for more relaxed versus dressier settings. Stiffer, more structured denim tends to look more formal, and longer pairs proportionally work best with heels. Short, loose, and frayed pairs are a great choice for casual daytime events.

The good news is, with so many unique cuts, colors and styles, you can wear jean shorts in every situation without ever having to repeat an outfit (though that's OK, too). Here are seven pairs that I love, and some inspiration on what to wear them with.

1. To Brunch

Dress up your Sunday brunch look with a knee-length pair of denim shorts. Flat sandals (because your feet are almost definitely in pain from all that dancing in heels you did on Friday and Saturday), a hat and sunglasses (to hide your hangover) are a must.

JBrand Beau Stretch-Denim Shorts, $170, Netaporter.com

2. To Work

OK, true — most jobs don't allow for jean shorts on the office, but if you work in a creative industry (or are lucky enough to work somewhere where "casual Fridays" are still a thing) it is possible to make it work. Choose a dark washed pair with a hemline thats at least longer than your fingertips (the longer the better), and wear them with a tailored shirt and a blazer. Loose fitting paper bag waist denim works too, and these styles tend to run longer. If you're wearing heels, make sure the shorts are long enough so the proportions don't look wonky. And remember — absolutely NO holes!

LOFT Frayed Denim Bermuda Shorts in Orchard Blue Wash, $54.50, LOFT.com

3. To Travel

Nothing says "summer vacation" like a good, old fashioned road trip: your feet on the dashboard, 1999 Britney Spears blasting through the speakers and of course, a comfy pair of jean shorts. Opt for a loose, boyfriend-style pair for maximum comfort, no matter how many hours you're stuck in the car.

AEO Hi-Rise Festival Shortie, $29.90, AE.com

4. To Meet Your Boyfriend's Parents

Since they're not quite shorts and not quite pants, denim culottes work in any situation. They're loose and airy, so won't make you as hot as regular jeans would, but seem a bit more sophisticated than your every day cutoffs.

Zara Denim Culottes, $29.90, Zara.com

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5. To A Party

Embrace the boho-vibes of your classic cut-offs by pairing them with an off the shoulder top (which is the trendiest top style of the season, by the way) and lots of gold bangles. Plus, it's a great excuse to bust out the booties that you didn't think you'd see again until next fall!

Plus Size Distressed Shorts, $19.90, Forever21.com

6. To A Dinner Party

Jean shorts, a white blouse and gold statement jewelry. Simple, easy and chic. This look works with dark and light denim, and either flat sandals and heels, and looks extra cool with a messy summer topknot.

Levi's 501 Roll Hem Denim Shorts, $68, UrbanOutfitters.com

7. On A Date

There's nothing better than summertime dates — you get to hang out outside and flirt while wearing your cutest clothing. Once a day-time staple, certain denim shorts styles can transition to night, too. Dress them up with a pair of heels, and pair with a sheer top. White jean shorts are just as versatile as white jeans, but Avoid anything too short, tight or ripped, and pay close attention to the proportions of your look.

Paige Denim Jimmy Jimmy Shorts, $129, Shopbop.com

Images: Courtesy of Brands; beeofdesign, micahginelli.com, justjilli.com