How to Wear a Hat

"I love hats, but I don't look good in them."

"I wish hats would come back in style."

"I just don't have any place to wear a hat."

"Everybody stares at me. I stand out."

"Hats don't fit my lifestyle."

"I can't find a hat that fits my weird head/face."

Remy doesn't like wearing hats.
But he's a dog. What's your excuse?

Other fashion experts and milliners have talked about this before. Here's my take. Here's how to wear a hat:

Decide You Want to Wear a Hat

The key word here is you. Don't worry about what other people are doing. Don't worry that you think hats aren't "in." First of all, they're more in than you think. If every person who says, "I wish hats would come back" actually wore a hat — guess what? — hats would officially be back. People aren't used to seeing hats everywhere, but they still like them. Second of all, unless you're in middle school, what other people think of your hat shouldn't be a concern. When I was in sixth grade, I thought if only I wore the right clothes, I would be popular. It didn't happen. Nobody's going to like you or dislike you because you wear a hat. And if they do, that says far more about them than it does about you.

If you want to wear a hat ... wear a hat! It's a simple as that.

Wear Red Lipstick, Part I (aka Don't Let the Hat Wear You)

Before I was a milliner, I worked as a makeup artist. The first time I ever wore a bright red lipstick, I was taken aback. Who was that person in the mirror? It was strange and uncomfortable ... at first. After about half an hour, I grew to love it! When I had women wanting to try red lipstick, they'd be nervous at first. I told them they just needed a little time to get used to it. Once they did, they could wear that bold lipstick with confidence.

And the same thing is true of hats. If you walk down the street ashamed of your fashion choices and feel insecure, if you think "Oh, everybody's staring at me because I'm wearing a hat!" then it isn't going to go well. "Why is she wearing a hat?" people might think, not because hats are odd but because you show your discomfort.

On the flip side, if you walk down the street pleased with your headwear and think "Heck yeah! I'm rocking this hat!" then you will feel great. You might get loads of compliments. ... And I guarantee you that at least one person will be thinking, "She can really pull off wearing a hat! I wish I could do that."

If you need to, wear a hat around your house to get used to it. Take lots of looks at your self in the mirror. Let wearing a hat feel cool and exciting, not embarrassing. And when you take it out in public, the #1 rule is this: You wear the hat. Don't let the hat wear you.

Wear Red Lipstick, Part II (aka When Style Does Matter)

You might want to pull out the
red lipstick and vintage hairstyle
for this 1940s-style hat.

If you grab a certain style of hat and just plop it onto your head, you might look kind of silly. Some kinds of hats require a certain type of outfit and/or hairstyle and/or makeup. Perching hats (such as the "doll hats" or "toy hats" of the 1940s) might look ridiculous with long, loose unstyled hair and jeans and a t-shirt. A pillbox stuck onto the back of your head will seem silly and out of place with no thought about makeup or clothes or hairstyle. Some hats require you to pay attention to the rest of your style. I advise starting with the hat and then figuring out the hair, makeup and outfit to match. And maybe wear that bold red lipstick for a truly vintage look.

But, the good news is there are plenty of modern "beginner" hat styles. Everyday, casual styles. Or, as I like to call them: jeans-and-a-t-shirt hats. 

Anybody who thinks they don't have a place to wear a hat is just plain wrong. Sure, you might not have an event that requires a wide-brimmed Kentucky Derby-style hat. Not everybody has a place to wear a sequined cocktail hat. But there are absolutely hats you can wear as easily as a ball cap.

The first hats I wore were probably newsboys and flat caps. From there, it wasn't much of a leap to wear fedoras/trilbies and cloches. A simple cloche or jaunty fedora can easily be worn with jeans and a t-shirt. 

You Can Be a "Hat Person"

"I don't look good in hats." "I'm just not a hat person." "I can't find a hat that looks good on me." "Hats always look silly on me." Milliners hear these all the time. 

And, sorry, but you're wrong.

"Saying you don't look good in hats is like saying you don't look good in shoes." I don't know who first said that. Sometimes it's expanded to include "You just haven't found the right hat yet."

An everyday fedora can go with
everything, even jeans and a t-shirt.

Another observation I love came from a fellow milliner. What would you do if you lived in the 1940s? You would find a hat that suited you because everyone wore hats. Period.

Obviously, not every hat is going to look good on every person. One of my favorite hat styles is the '40s style fedora that is a bit smaller than head-size, so it perches on top of the head. One of my favorite people is a woman who is 6' tall and has a 24.5" head size. If she wore this style of hat, it would probably look like she just has a too-small hat, rather than looking like the style. If you have a long, thin face, a high-crowned, wide-brim hat might not be the best match for you.

So experiment. See what you like. See what looks good. And milliners are not just hat makers. We're also hat stylists. I can help match you up with the best style for you. I can make a custom hat to suit your style. If you have an extra large or extra small head size, I can make a hat to your measurements. And if I'm not the right milliner to make the bespoke hat, I will refer you to another milliner who is.

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As always, questions are welcome.