Stetson's CEO on Hats

By CHERYL LU-LIEN TAN

Pam Fields, chief executive officer of Stetson Worldwide, wears hats three or four times a week. After all, she has access to what she calls "the greatest lending library of hats"—the showroom of her company, which makes a variety of men's and women's styles beyond the famous cowboy hats.

Ms. Fields is partial to fedoras and newsboy caps for herself. She likes the versatility of fedoras, which she says can be worn with tailored suits or little black dresses to black-tie events or can be paired with a mannish shirt, skinny jeans and cowboy boots.

View Full Image

Michael Jurick

Stetson CEO Pam Fields

With newsboy caps, she'll often add a tweed version to a sweater and a pair of jeans for her children's soccer games or casual Fridays at work. "I want something that I can crush and stick in my back pocket," she says.

Unless she's wearing a black fedora with a black dress, Ms. Fields generally avoids being "matchy-matchy." She tries not to match the color of her hat to any clothing item, noting that "you're not going to find that red hat that matches your red skirt perfectly," Instead, she'll wear a tweed topper whose pattern might have a strand of color that's reflected in her clothing.

Another don't for Ms. Fields: "If you're wearing a patterned shirt and a contrasting patterned skirt, you don't want a third pattern on your head," she says.

When she chooses a hat, one of her key criteria is reminiscent of picking out makeup: She tries to complement her complexion. "If you have sallow skin, you don't want to wear a hat with green undertones," she says. "If you have very pale, creamy skin, you might be best served not to wear a heavy black hat."

In Ms. Fields' case, she has somewhat fair skin with a slightly rosy undertone, so she tends to wear black, brown or gray hats—or maroon, orange or rust "if I want something that gives me a lift." She steers clear of yellow or green, which, she says, "make me look like death."

Ms. Fields also advises taking face shape into account. "If you have a very round face, you don't want to wear a very round hat," she says. "You want to make sure there's some degree of opposition." A slightly elongating hat is flattering on a square-faced woman, she adds.

Proportions are important, too. "If you're petite, a very wide-brimmed hat will look like a flying saucer on your head," says Ms. Fields, whose slender build is one reason she sticks to narrow-brimmed hats and caps.

Ms. Fields tries to buy hats that are sold by size and fit her exactly. Not only is it more comfortable; it also helps her avoid having hat hair. Still, if she has an elaborate hairdo, she does skip the hat.