And Just Like That, Khaki Shorts Are Cool for Summer 2023

While there’s no denying that a certain insurance agent’s signature pair of khaki pants and fire-engine red polo is iconic, it also gives me unwanted flashbacks to when I wore almost the same uniform as a waitress. Still, I’d argue that the beige bottom doesn’t deserve the bad rap it's amassed over the years; that if we figured out what to wear with khaki shorts to make them look and feel more fashion-forward, society as a whole would be more inclined to wear them in and outside the workplace. 

In an interview with InStyle, stylist Madeleine Kennedy explained that khaki wasn’t originally designed for fashion so much as function, manufactured as an alternative to the wool uniform worn by the British Indian army in the mid-nineteenth century. “Wool was too hot and itchy,” Kennedy notes, while khaki, she says, was “more breathable and lightweight.” By World War I, khaki was a staple in the U.S. Army uniform and was introduced to the consumer market in 1905 by none other than Levi Strauss. 

Still, khakis didn’t catch on in a fashion-forward way. They were largely associated with the coaches of sports leagues and school dress codes, Kennedy says, adding that this is likely why we struggle to see khaki's potential in a stylish setting. Her solution? Reframe your mindset by thinking of khaki shorts and pants like you would jeans.

“[Like denim], khaki is a nice base piece to build on, is very versatile, and goes nicely with colors and patterns,” Kennedy says. “It can be elevated by pieces that bring personality and chicness to an otherwise simple pair of shorts.”

Ahead, I asked stylists for their best tips regarding what to wear with khaki shorts to make them feel stylish. Needless to say, their responses were full of inspiration.

Focus on Feminine Contrasts

San Diego-based personal stylist Jaquelyn Wahidi recommends pairing the shorts with a feminine top. “I think a blousy, white button-down with puff sleeves would be ideal,” Wahidi tells InStyle over email, adding “a pair of nude sandals and a Panama hat” would complete the look nicely.

Add Elegant Elements

As the saying goes, it’s all in the details. Personal stylist and style coach Samantha Dawn tells InStyle that one of the simplest ways to dress up khaki shorts is to mix elegant elements into your ensemble. Examples include feminine necklines, silkier fabrics, and accessories like statement earrings or a sleek leather belt. The trick is to make khakis feel less boring, and Dawn assures these kinds of components can make the bottoms feel “more elevated and chic.”

Play with Proportions

For high-waisted, wide-legged khaki shorts, style blogger Ingrid Leo suggests complementing the fit with either a form-fitting or tailored blouse with subtly puffed sleeves. The interplay of proportions “adds a fashionable touch to your outfit ensuring both comfort and sophistication," Leo tells InStyle.

Be Bold with Your Color Pairings

Khakis are the ultimate earthy neutral (reminder: Khaki is a color, not a material), making them the perfect canvas for bold hues. Leo encourages anyone experimenting with khaki shorts this summer to also toy with unexpected color patterns, like “a bright coral top or vibrant turquoise blouse,” for a finished look that is both playful and fashion-forward. 

Add Flare with Footwear

In addition to your top, your footwear can play a key role in how your khaki shorts outfit comes together. For example, Leo points out that something like an espadrille wedge can offer a comfortable and sophisticated bohemian vibe with its natural materials and woven textures, while a sandal or mule offers an effortless look. “Strappy sandals with metallic accents add a touch of glamour and sleek, minimalistic mules lend a more modern style,” she adds. Consider the aesthetic you’d like to achieve and pair accordingly.

Lean into Nautical Prep

Outside of restaurants and insurance offices, khakis serve preppy vibes. Max Dubinsky, the owner of slow fashion boutique Fancy Groceries, wants you to channel that aesthetic, but in a way that makes sense for summer.

“For women, an open chambray or denim button-up paired with a white tee or tank tucked in with Birkenstocks [for footwear] is a great khaki shorts look for the upcoming season,” Dubinsky tells InStyle. If you need more of a visual to nail the look, the personal stylist recommends turning to the Kennedys for dressy-casual inspiration. “JFK popularized the khaki as leisurewear outside the office, and his nautical style still holds up today.”

Squash Tradition By Adding Some Edge

As far as Jen Principe, stylist and founder of The Phoenix Effect NP, is concerned, updating your khakis is just a matter of going against the grain and swapping traditional pairings with edgier ones. Her style vision: A bandeau top with a cropped blazer, some killer jewelry, and a sexy or edgy shoe.

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