The right hat for your face
A good hat can upgrade your entire look, pulling an outfit together while giving you a chic, confident air. Luckily, there's a style for everyone out there. But the trick to finding "the one" has to do with the proportions of your face. "If you have a small face, a smaller hat will suit it, whereas a larger hat will overwhelm it and only make your petite features appear smaller," style expert Jennifer Chan says. "If you have a larger face, you will need an equally sizable hat to complement it." Finding the perfect hat shape for your face, she adds, is all about creating balance and working with your natural features to juxtapose elements you either want to highlight or minimize.
If you have a round face
"It's all about opposites," Chan says. She suggests going for a hat with "angular curves" to play up the youthful shape of your face. But avoid anything that's overly rounded, as that will only emphasis the fullness and volume of your face. Try a fedora, a porkpie hat, or a newsboy cap (angle it to the side a bit to add some dimension and asymmetry). It helps to also have the right hairstyle for your face shape!
If you have a heart-shaped face
Lucky you: You'll look good in pretty much any style, especially a hat with sharp angles or a short brim. Why not try a fedora, a jockey cap, a baseball cap, or cloché? If you'd like to draw attention away from a wider forehead and balance out your narrow chin, try a bucket hat instead. Don't miss the simple style upgrades that will make you look expensive.
If you have a square face
Go for a floppy or a bowler hat—anything that's soft or slouchy will soften and round out the strong angles of your face. Other good options include beanies and berets, as long as you avoid anything too structured or angled (such as a fedora or trilby), which will simply highlight your sharp features. These outfit tricks will make you look younger.
If you have an oval or oblong face
Remember: Opposites attract! If you have a longer face, a hat with a short brim or a floppy hat will add width and dimension, Chan says. Anything with too much height will elongate your face further.
Play with shapes and styles
The only real way to figure out if you like the way a hat looks on your head is to try on as many as possible. If all else fails, Chan suggests throwing a baseball cap on before you head out. "Baseball hats can pretty much flatter anyone and look great if you're running errands or attending a casual sporting event," she says. "A lot of celebrities are bringing the baseball cap back for a chic street look and opting for cool fabrications like neoprene, leather, mesh or suede in solid shades versus anything with a logo or team name on them. Athleisure is more popular than ever, and a cool baseball cap is an easy way to pull it off without trying too hard." Here's how to establish your personal style.