How to Wear: Shorts, Three Ways

This post feels like a long time coming, after our Pick Six: Shorts for Summer blog post and inclusion of shorts in our Independence Day Style post. We’ve danced around styling shorts on the blog all summer, and we decided it was time to face the controversial clothing item head on while there’s still lots of time to wear them. In the South, where the hot temps linger well into November, shorts are as much a fall staple as a summer one.

How to Wear Shorts, Three WaysIt seems that women either love or hate shorts, I think because of their unflattering stereotype and that they are rarely styled outside of a casual weekend outfit. What really prompted us to focus on shorts with this post is that we think they can actually be (dramatic pause) work appropriate! And we want to show you how and then some. We chose the basic 5-Inch Stretch Chino Short in Frosty Olive by J. Crew as the feature of three distinct looks: 1) Bachelorette Bash, 2) Business Casual, and 3) Sunday Funday.

(P.S. – for more in-depth guidance on finding the right fit of shorts for your body type, contact us directly!)



Did you know that Nashville is the nation’s capital for bachelorette parties? This look is perfect for going out, whether you’re with your girlfriends or your honey. An off-the-shoulder top begs for a statement necklace or two layered, and strappy high heels never disappoint on upping the ante, no pun intended.

How to Wear Shorts, Three WaysClockwise from top left
Malaina Top in Pure White by Club Monaco
Edda Link Necklace in Black by Rachel Comey
Mia Necklace in Ivory by Anthropologie
Opal Sandal in Pearl Leather by Schutz
Striped Box Bag in Mother of Pearl by Zara



Throw on a blazer and some loafers and, voila!, shorts are professional attire. Of course, length plays a huge part on the appropriateness level when it comes to shorts, but the 5-inch chino short from J. Crew is right on the money for most people. Keep it French girl classic with a muted color palette and easy-breezy flair.

How to Wear Shorts, Three WaysClockwise from top left
French Girl Blazer in 365 Crepe Oyster Grey by J. Crew
Terek Silk Top in Blanc de Blanc by Club Monaco
Keyhole Reading Glasses in Sea Mist by J. Crew Factory
Edie Leather Loafers in Warm Beige by J. Crew Factory
Woven Leather Bucket Bag in Black by Zara



Although athleisure has a time and a place (and we’re so thankful it does!), sometimes it’s fun to dress with a little spunk on Sunday, especially when you’re running around with friends. It’s hard to feel frumpy in ruffles, and we seriously cannot get enough of the straw bag trend. It screams laid-back and carefree.

How to Wear Shorts, Three WaysClockwise from top left
Bindell Top in Blue/White by Club Monaco
Tract Spiral Drop Earrings in Sky by Rachel Comey
Sandbar Straw Crossbody in Natural by Free People
Angie Platform Sandal in White Leather by Ugg
Retro Round Frame Sunglasses in Off White by Gap


We couldn’t resist the chance to share a few more J. Crew shorts styles we’re loving. If the 5-inch chino isn’t your thing, see what you think of these:

How to Wear Shorts, Three WaysClockwise from top left
Tie-waist Short in Honey Brown Cotton Poplin by J. Crew
High-rise Denim Short with Button Fly in Primrose Wash by J. Crew
Rope Waist Pleated Shorts in Ivory/Navy by J. Crew
Tie-waist Short in Navy/White Clip Dot by J. Crew

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