Sporty Chic: Baseball Hats

Top off your look, from left to right: Clare V.’s Oui hat, Lilly Pulitzer’s vibrant print and Free People’s self-tie Bow Peep.

By Janet Kelly

WE’RE CELEBRATING “take-me-out-to-the-ballgame” season with a post on baseball caps.

In addition to “’tis the season,” what spurred our interest was a recent Major League Baseball (MLB) story on the history of the headwear. The “quintessential piece of a ballplayer’s uniform,” it was also an “egalitarian wardrobe accessory” for everyone from taxi cab drivers to rock stars. Baseball’s first official team, the New York Knickerbockers, who formed in 1845, didn’t wear hats at all until four years later, when they began sporting straw hats. By the late 1850s, though, players were donning something much closer to what we think of as a baseball cap—a crown with a bill that comes out just one direction instead of all the way around and keeps the sun out of the team’s eyes—to catch fly balls more easily.

The everyman hats enjoyed a popularity boost— plus, a touch of opulence—when father and son, Logan and Kendall Roy, wore their Loro Piana cashmere caps (whispered wealth) on several episodes of HBO’s hit show Succession.

As for the MyLittleBird team, we’re not too rich for hats with prints, logos or bows—we wear them for functional and stylish reasons. For example, my white, swoosh-adorned Nike cap (along with sunglasses and a lotta sunscreen) protects my face from getting burnt during tennis clinics. Our amazing managing editor, Nancy McKeon, wears her hat and her hood in the rain to trap her hair and keep it from “going nuts,” while Late Dates writer Grace Cooper puts on hers for dog walking, pickleball and running out to the grocery store—to hide bedhead, thinning hair and protect against “skin cancer with that big visor.”

On the subject of bills/visors: If they interfere with how you’re seeing, they can be a hindrance. A 2014 NIH study says a big brim can affect visual perception and that—ahem—older people should be aware they could be a falling hazard.

So, forewarned is forearmed when choosing a baseball cap. Here are some of our favorites:

Photo courtesy of HBO.

Kendall Roy’s (Jeremy Strong) luxe but boring  Loro Piano cashmere cap ($525) reflects his family’s outlook on designer logos and any sort of display of wealth.

Channel the glamour of the French Riviera in its heyday with Fendi’s foulard hat. Speaking of subtle luxe, the cap is made of silk in a trompe-l’oeil print of interlocking FF’s and a coordinating soft leather visor. The beige combo is sold out; the green (above) and the black versions sell for a heady $650.

From Helen Kaminski, known for modern, stylish designs and using the finest raffia (from Madagascar), comes this cap ($210) with a full-coverage—UPF 50+—canvas brim (4.7 inches wide), an elastic inner band and an adjustable back-buckle strap.

If you’re in search of serious sun protection, look no further than sun-protective clothing company Coolibar, which has received the Skin Cancer Foundation’s Seal of Recommendation. The Olivia Convertible Sun Visor comes with a UPF 50+ rating, sliding side panels in the brim for adjustable coverage, an internal sweatband and an anti-glare under brim to reduce reflecting glare. It sells for $49.

This Bow Peep cap combines a baseball hat design with a quilted flower pattern and self-tie bow at the back for a fun, feminine interpretation of the classic. It’s $30 at Free People.

Wrapped in a signature Lilly Pulitzer vibrant print, the Run Around Hat ($38) is the kind of  topper to wear when you want to hide your uncombed hair, tip down the brim to cover your still-sleepy eyes and hurriedly head out of the house knowing that your summery cap will make amends for all.

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