DO: Start small
“If you’re new to hats, try a really good neutral—brown, black or cream—and then branch out into colors. Start basic and build from there.”—Delaney Reese, MODERN Society
DON’T: Be afraid to go big
“A hat is a great way to draw attention to your face—and just to you, in general. People always look at the girl in the hat.”—Teri Poindexter, Springfield-based milliner
DO: Choose the proper size
“A lot of people are scared of hats if they don’t fit perfectly. How you wear a hat on your head, your crown shape, how much hair you have, the size and shape of your face—they all affect your hat size.”—D.R.
DON’T: Give up
“If the hat you love isn’t a perfect fit, consider a hat filler, which is a foam lining with a little adhesive. You can line the entire hat or just a portion of it to make the hat fit its best. Customizing your fit can make you much happier with the look.”—D.R.
DON’T: Unintentionally change your face shape
“Placement is important. Many people immediately pull the hat down to their eyebrows, and then they feel alienated because it completely changes the way they look.”—Emma Lee, 5 Pound Apparel
DO: Use it to accessorize your favorite features
“I always make sure to wear mine with a little of my hair showing.”—E.L.
DON’T: Frizz out
“A silk barrier can help with hat hair. Some hats, like berets, often come with silk lining. And if your favorite hat isn’t lined, you can style it with a silk scarf between the hat and your hair.”—John Fahey, Wallace Rae Salon
DO: Give your hair extra care
“Remember that in winter, your hair tends to dry out, which contributes to frizziness and flyaways, especially when you’re wearing a hat. Adding a deep conditioner to your routine will help.”—J.F.
DO: Keep your options open
“If you can’t find a hat that works with your hair, consider cold weather alternatives, like a cute pair of earmuffs.”—J.F.
DO: Get inspired by past beauties
“For special occasions, I love 1930s and 1940s cloche styles and percher-type hats. They are always very flattering.”—T.P.
DO: Take a cue from your own closet
“Know what colors wash you out, or bring someone with you who can tell you. This will help you choose something that works with your skin tone.”—E.L.
DON’T: Fight that feeling
“A beautiful hat really elevates your outfit. So you can do something simple with your clothing and let the hat take center stage.”—T.P.
Find this hat and more from local boutiques like Town & County, Clothe Boutique and MODERN Society.