You Asked, We Answered: How To Wear Boyfriend Shorts

By now, we’ve all mastered the boyfriend jean look – but what about its cousin, the boyfriend shorts? Whether you bought an actual pair of boy shorts (like me) or followed the DIY route – you may be wondering what to do with your new oversized acquisition. R29 reader, Ashley T. from Washington, D.C. asked me this exact question, “We all dig boyfriend jeans but how do you wear boyfriend jean shorts?”
Coincidentally, I had just tried solving this conundrum myself. On a whim, I purchased a pair of oversized denim shorts from the men’s sale section and came home not knowing what do with them. After a little experimenting with my closet staples, I’ve come up with three looks that pair harmoniously with boyfriend shorts.
My first thought is to fight boyish with cute. So I paired the boyfriend shorts with a pretty embroidered sweater, my favorite pink, bow heels, and a bright yellow clutch. I found the shrunken proportions of the cardigan played well against the slouchy-ness of the shorts.
Zara mens distressed shorts, Field Flower Anthropologie embroidered cardigan.
Photo: Courtesy of Marshall Johnson.
A girly pair of bow heels lends the right amount of juxtaposition to the oversized boyfriend shorts.
BCBG heels.
Photo: Courtesy of Marshall Johnson.
I wanted my boyfriend shorts to be cut right above the knee – these were a little long so I cuffed them to get the look I wanted.
Gap yellow clutch.
Photo: Courtesy of Marshall Johnson.
When trying out a new trend, I like playing with contrasting proportions, silhouettes, and styles. For this look I wanted to contrast the casual ripped shorts with a structured blush pink blazer and sleek heels. I kept the look simple by adding a basic gray tee and a blue printed clutch.
American Apparel T-shirt, H&M blazer.
Photo: Courtesy of Marshall Johnson.
These sleek mint-colored heels complement the structured blazer and add just a little pop of color to the outfit.
Christian Siriano for Payless Mint Mary-Jane Heels.
Photo: Courtesy of Marshall Johnson.
This printed clutch in a similar blue color to the denim infuses the look with some welcome texture.
Felix Rey ikat clutch.
Photo: Courtesy of Marshall Johnson.
If you’re going to borrow shorts from the boyfriend, you might as well get the entire outfit from his closet — okay, maybe not literally, but in spirit. This time I paired the denim shorts with wingtip brogues and a button-down shirt for an all-menswear-inspired look. Make sure to pick a fitted blouse or tuck in a looser one so the outfit doesn’t look frumpy.
Ralph Lauren pinstripe shirt.
Photo: Courtesy of Marshall Johnson.
These gorgeous, vintage Chanel wingtip oxfords are the perfect menswear-borrowed shoes to go with boyfriend shorts.
Chanel vintage shoes.
Photo: Courtesy of Marshall Johnson.
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