How to Wear Tailored Shorts for Summer 2023

What makes tailored shorts different from other shorts styles? For one, they can be a pain in the butt to style. Though 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 zhush to your next business casual look.

With a Striped Sweater

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 girlies drooling, while still keeping you from freezing at a nighttime beach bonfire.

With a Sheer Blouse

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 murky or patterned in a way that matches the shorts.

With a Micro Bandeau Top

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

For a vibe that remixes Fashion Week guest 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

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

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 solid colors are still equally sweet.

With an Oversized Vest

An oversized vest will add a whisper of quiet luxury to your fave 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

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

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

Make a major fashion statement that still carries the polish of a business casual 'fit by wearing linen tailored shorts and a matching floor-length linen blazer. For even more impact, go bare under your statement outerwear.