Whether you’re thinking about wearing a fedora, a sun hat or a really stunning fashion hat, you need to follow the same simple rules to pull it off in style. From the right proportions for hats, in relation to both your frame and face shape, to the right style tips, discover the best rules of hat wearing.

Choosing the right hat that fits your style might be easy, but pairing it with your entire outfit and keeping in proportion and in accordance with etiquette for formal events takes a bit more effort. Discover the most important rules on how to wear a hat.

Be Careful with Proportions

A very important rule on wearing a hat, that applies to both fedoras and more elegant fashion hats, is to make sure it works with your facial bone structure. 

The crown of the hat should never have a smaller crown than the distance between your cheekbones. Once that detail is in order, you need to be careful how the hat works with your shoulders and your entire frame.

Floppy Hat Outfit With Shorts
photo: Bebe Zeva

Even when you’re wearing a wide brim hat, you need to make sure it works with your shoulders. If it’s the exact width of your shoulders, slightly bigger or smaller, you might not get the best look. Petite women should not wear hats with very wide brims, while a floppy, wide brim work better for a tall frame.

All Black Outfit With Hat
photo: Mira Berglind

Follow Hat Etiquette

When you’re wearing a fashion hat, you can get away with keeping it on most of the time without breaking any rules of etiquette. Baseball caps don’t count as hats, so you should probably get used to taking them off, whether it’s when you enter a public building, a restaurant or someone’s home.

Wearing A Hat With Jeans
photo: Anouska Proetta Brandon

The main rule for fashion hats is that you absolutely have to take them off when they’re blocking someone else’s view, whether it’s at a wedding or other social event or during a movie or play.

Choose the Right Hat for Your Face Shape

While knitted hats, like beanies, and alice band hats work for most face shapes, you need to be a bit more careful when you’re picking a hat that will look flattering on you. It all comes down to your face shape.

Oval faces can pull off most hats, but if you have a heart or diamond shaped face, you shouldn’t wear hats with wide brims. They’re not flattering because they’ll make your chin look pointy.

Wide Brim Hat Retro Outfit
photo: Cosette Munch

For a round face, stay away from small and round hats and instead go for a tall crown. Make sure the brim of the hat is wider than your face and choose a slanted or peaked crown.

If your face is square or you have angular features, go for a soft hat and wear it high on your forehead. Choose round lines, like the bowler hat, or go for big floppy brims.

When you’re wondering how to wear a hat if your face is long, go for bigger and softer brims.

Schoolboy Hat Outfit
photo: Ebba Zingmark

Stick to the Rulebook When Accessorizing

If you haven’t found the perfect hat and you want to add anything to it, follow one of the most important rules on how to wear a hat and stick to the right hand side of the hat. You may think it’s old fashioned, but men are still advised to use the left side, while women can add embellishments like feathers or flowers on the right side.

Straw Hat Summer Outfit
photo: Tini Tani

Don’t Go Matchy-Matchy

Whether you’re looking for a hat for a formal event or for a more casual look, you shouldn’t try to match its color exactly to your look. If the hat is the same color as a big part of your outfit, it will get lost and make your outfit look like a costume instead of being the accent you want. That goes for any color, including black. Unless you’re going to a funeral, don’t wear a simple black hat with a black outfit.

Vintage Hat Outfit
photo: Rachel-Marie Iwanyszyn

Get the Right Hairstyle

Unless you’re only planning on wearing the hat for a few seconds before taking it off, straight bangs don’t go well with hats. Style your bangs into a side-swept look to go better with a hat or expect to find your bangs ruined when you remove your hat.

Boho Outfit With Large Hat
photo: Bebe Zeva

Choosing Hats for Formal Events

One more thing to remember when you’re looking for the right way to wear a hat at a formal event, is to make sure the size of the brim suits the time of day. If you’re planning to wear a hat in the morning or late evening go for a smaller one. Wide brims are better suited to noon and afternoon events.

Large Black Hat With Dress
photo: Bebe Zeva

See also:
Plus Size Fashion Rules to Break!
Style Tips from Rachel Zoe