Fashion & Beauty

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.

This might be the perfect gift for a baseball-loving-or-not June bride. Eugenia Kim’s pale pink organza Lauren Cap with a matching flowy bow is a feminine twist on the traditional sporty headwear. It sells for $90.

Quaker Marine Supply closed down during the Great Recession, but one of the company’s most popular caps, this sturdy twill Quaker Marine Swordfish Hat, is being manufactured again in the original 1950s factory in the U.S. The company’s founder and Coast Guard veteran, Joe Kadison, designed it, based on his experiences on the water. The bill is 3 3/4 inches long with a low profile to reduce the effects of wind and has four eyelets on each side panel for ventilation, along with a dark green underbrim to absorb reflected light. It sells for $38 at Todd Snyder.

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.

Go for the green and the pop of white lettering on a Clare V.-designed baseball cap with a 2.5-inch brim and a certain je ne sais quoi. It sells for $49 and is also available in navy corduroy.

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.




MyLittleBird often includes links to products we write about. Our editorial choices are made independently; nonetheless, a purchase made through such a link can sometimes result in MyLittleBird receiving a commission on the sale. We are also an  Amazon Associate.

If this post was sent to you by a friend, you can sign up for the newsletter at the very, very bottom of this page.

5 thoughts on “Sporty Chic: Baseball Hats

  1. Nancy G says:

    I love hats! I have many more than I need. Since I started walking for exercise though, I need the sun protection and a place for my ponytail – hence, all my baseball hats. Mine are pretty utilitarian. But I’m looking at the Free People one…maybe the Lilly Pulitzer too.

  2. cynthia tilson says:

    Love this one! The Lilly Pulitzer is adorable – must buy it! And please tell Mr. Roddy that there is a great straw hat vendor at the 3 Rivers Art Festival this year, in the Dioum Basket booth. Beautifully handcrafted!

  3. Carol says:

    ahhh hats! I remember when ladies had to wear a hat in church, that’s the last time I had a bunch. I do have one baseball hat that I wear on a sunny morning on weekends to shade my eyes, otherwise, no hats for me (although I love the white “free people” one!!! I may have to invest in a second hat. 🙂

  4. Jim Roddey says:

    Where can I get a summer straw hat?

    1. Janet Kelly says:

      Cindy T. says there’s a straw hat vendor at Three Rivers Festival in Pittsburgh if you go to the Dioum Basket Booth.

Leave a Reply

Your email address will not be published. Required fields are marked *