How To Wear A Hat: 10 Tips For Wearing It With Confidence 

Ready to add a hat to your style mix? They’re a stylish and useful accessory– but sometimes, hats are intimidating! Don’t fear. With a few tips, you’ll be wearing yours like a pro. Here’s what you need to know about how and when to wear a hat.

1. Find your hat size

Just like any item of clothing, fit is the first step. Before you pick a style, find our your hat size. The hat brand you choose should have a size guide that you can use to find your fit. To measure, you’ll want to find the circumference of your head. Use a soft tape measure and place it about ½ inch above your ears. With this measurement, you’ll be able to properly size any hat you want.

When you try on your hat, it’s easy to know when the fit is right. If it’s too tight, you’ll feel squeezed. And you might even get a little headache! And if it’s too loose, it’ll easily slip off your head or down over your ears. The perfect fit will be snug but easy to take off and put on.

2. Discover your face shape

Now that you know your size, it’s time to think about hat styles. The best hat is always the one that you feel the best in. But, finding styles that are a good fit for your face shape is a good place to start. There are five face shapes that most people relate to: round, oval, square, diamond, and heart shaped. A quick search of each will make it easy to find the shape that fits your face the closest. Then, use a face shape guide to find the hat styles that will flatter you the most.

3. How to choose a hat: start simple

When you’re new to wearing a hat, it’s easy to feel like your new accessory is “too much.” So, start with a simple, classic style. Often, smaller hats feel more comfortable. That’s why berets, newsboy, and fedora hats are a good choice. When it comes to color and pattern, think neutral. If you want to keep a low profile, solid tones likes black, grey, and nude won’t attract as much attention. And, they’re easy to style with many pieces of clothing.

4. Find a style you love

While some hats will accentuate your facial features slightly better than others, there’s no match for a style that makes you feel great. So take some time to play with different hat styles. You might be surprised by the hats that you end up loving. And, don’t be afraid to play with contrasting styles either. If you typically prefer feminine, flowy clothing, try on a structured bucket hat. It just might offer the perfect amount of balance for your look.

5. Practice first

Does wearing a hat out in public make you nervous? You’re not alone! To get comfortable in your new look, practice a few times at home. First, make sure you know how to put on a hat properly. It should fit snugly across your forehead. And never slip down over your ears.

Ready to head outside? Wear your hat on your morning walk to get the mail or newspaper. Then, try it out on a quick coffee run. As you get used to the new accessory on your head, it’ll feel like a natural part of your outfit. Just like a new jacket or pair of jeans, a new hat might take some wearing in to feel “just right.”

6. Match the season

Not sure where or when to wear a hat? Start with the seasons! Summer is a big time for hat wearers. And for good reason. A UPF rated hat can protect you delicate skin from long-term damage (and a short-term sunburn). In the summer, choose beachy materials like organic raffia or straw. And don’t be afraid to rock a wider brim. With the sunshine beating down, you’re sure to be surrounded by many more hat-wearers than usual.

If you’re starting your hat-wearing journey in cooler weather, consider cruelty-free wool styles. This versatile, attractive material is never out of fashion.

7. Avoid costume-y looks

There aren’t many “don'ts” when it comes to wearing a hat, but this piece of advice could come in handy. When you’re first styling an outfit with a hat, it might feel natural to try and best “match” your hat style with your clothes. So, if you’re wearing a flannel and cowboy boots, a cowboy hat may feel appropriate. But if you’re wearing the outfit in the city, you may end up looking like you’re attending a costume party. Instead of matching in this way, consider styling your hat with an outfit that has a similar level of fanciness. For example, a semi-casual sundress could pair well with a quality-made boho hat. 

8. Keep other accessories to a minimum

Adding a hat to your look is a fantastic way to spice it up. But be aware of the space that your headware takes up. If you’re rocking a wide-brim hat, a big set of earrings may overpower your face. Similarly, a large belt buckle and a colorfully banded fedora might clash for attention. As a general rule of thumb, consider keeping your other accessories to a minimum when you wear hats. As you get more comfortable wearing hats, play with adding in more layers to your look!

9. Make a proportional outfit

It’s easy to focus on how your face looks in a hat. But don’t forget about the rest of your body! Use a full-length mirror to see how your hat interacts with your entire body. And play around with making the outfit as proportional as you can. For example, a floppy, wide brim hat paired with a shirt with puffy sleeves and skinny jeans may look top-heavy. To even it out, the same hat paired with a simple top and wide-leg jeans would offer a more balanced look. If you choose a smaller hat, a shirt that pulls more focus might be appropriate.

10. Have fun

No matter what hat you choose, the most important factor when learning how to wear a hat is how you feel in it. And if you’re fretting about when to wear a hat– remember, wearing it isn’t a permanent decision. And, modern hat etiquette is much more relaxed. If you’re ever feeling uncomfortable, you can always take it off! So take a deep breath and go for it. Chances are, you’ll be stopped by more than one person asking, “where did you get that hat?”