What makes tailored shorts different from other styles of shorts? For one, they can be a pain in the butt to style. Although the name suggests you’ve seen a professional, tailored shorts don’t necessarily have to have undergone literal tailoring to fit your body like a glove. However, they do tend to have more in common with a pair of business casual pants than your standard summer cut-offs. You’re likely to find traditional pockets and belt loops on tailored shorts, and they’re also commonly found in trouser-like materials such as linen and cotton.
That’s not to say that tailored shorts can’t be fun. Slap a print or exciting embellishment onto ’em and you’ve suddenly got a ‘fit that not only fits, but slays. Ahead, we’ve rounded up ten exciting ways to wear tailored shorts because to add a little zush to your next business casual look.
With a Striped Sweater
Getty Images
Complete your Hamptons getaway packing list with a lightweight striped sweater and a pair of tailored shorts, inspired by Kate Middleton. This look will have coastal fashion girls drooling, while still keeping you from freezing at a nighttime beach bonfire.
With a Sheer Blouse
Getty Images
One way to instantly give tailored shorts a sultry makeover is to add a sheer top. The look can maintain the elevated air of the bottoms, especially if the sheerness of the top is a bit gloomy or patterned in a way that matches the shorts.
With a Micro Bandeau Top
Getty Images
Give a pair of long tailored shorts a sultry update by pairing them with a micro-bandeau top. Trust us, the look sings on its own, especially with a top knot and a pair of sleek pumps. Or, you can add a more casual vibe and some extra coverage with some chunky sandals and a chambray button-down.
With a Tie and Fishnets
Getty Images
For a vibe that remixes Fashion Week guests with high school valedictorian, try wearing a pair of tweed tailored shorts with a textured tie and fishnet stockings. A statement bomber jacket will amp up both of this look’s personalities, but isn’t required.
With a Lace Bra Top
Getty Images
Extend the decadence of a pair of brocade or printed tailored shorts through your entire outfit by wearing them with an elaborate lacy bra top. For extra fashion impact, we recommend adding a matching blazer.
With a Retro Collared Blouse
Getty Images
For a vintage beachy vibe, grab a basket tote and slip on your comfiest espadrilles and a button-up blouse with a retro peter pan collar. A retro collared blouse in a gingham or floral print adds even more summery femininity, but the solid colors are still equally sweet.
With an Oversized Vest
Getty Images
An oversized vest will add a whisper of quiet luxury to your favorite pair of tailored shorts. Wear it open with a satin bra top, tied at the waist for a more casual vibe, or buttoned up and belted for a more cinched silhouette.
With a Matching Blazer
Getty Images
Tailored shorts get a glam update when you opt for a printed pair like Amanda Seyfried’s, and that modern feel is only amplified when you add a matching printed blazer. It doesn’t get more mod than this.
With Tights and a Cropped Jacket
Getty Images
All you need to give a pair of tailored shorts a bit of an edge is a pair of sheer tights, chunky loafers, and a cropped jacket.
With a Trench-Length Linen Blazer
Getty Images
Make a major fashion statement that still carries the polish of a business casual’ fit by wearing tailored linen shorts and a matching floor-length linen blazer. For even more impact, go bare under your statement outerwear.
