Illustration by Ariana Villegas


How To Become A Hat Person, According To Hat People

Your guide to not being intimidated by Fall 2019's biggest accessories trend

As 2019 strengthens its position as the year of the hair accessory, a new contender is coming for the top spot that's so far been occupied by hair clips and headbands. I'm talking about hats, of course, which were all over the Fall 2019 runways, and the more unconventional, the better.

While this is great news for hat people, what if you're too afraid of hats to try them out for yourself?

Which, we get it. Hats can be intimidating. Whether you're afraid they'll be too big or statement-making for your personal look, or you simply shy away from out of the sheer fear of people thinking you're wearing a fedora (when it's clearly not a fedora), fully embracing a hat-wearing lifestyle is not always the easiest thing to do.

In our minds, there are hat people, and then there are those who wish to be hat people. So we turned to the expert hat people—those that make hats and those that wear hats, and those that, of course, do both—to get their tips on finding the best hat for you.

Read on, dear friends, so that you can become a hat person this fall.

Know what styles work best with your face shape

When it comes to finding a hat that works for you, knowing your face shape and what kinds of styles will flatter it most is the first step.

As Courtney Bagtazo, founder of genderless hat label Bagtazo, explains, the crown and brim have to be taken into consideration based on your face shape. "People with round faces can usually pull off almost any hat, but that's because the ratio of the crown and brim don't overpower their entire look. The same goes for people with a lot of hair." If you have a petite or heart-shaped face, you'll want to opt for hats with a balanced brim width-to-crown ratio. "One of my first hats ever made, the Mountain Hat, has a very tall crown, but the brim length is almost the same measurement as the crown height, so even a person with an extra small head size and petite face looks great in it," she says.

When it comes to square faces, Bagtazo suggests avoiding styles with flat crowns. "These tend to not work out for people with square-shaped faces because it's just too much square for one look. And, as [photographer] Irving Penn showed us so well, a strong jawline and a lampshade brim were clearly made for each other."

Though, she stresses that, while face shape is definitely a factor, it really is all subjective. "There are plenty of Bagtazo customers who have self-proclaimed 'tiny faces,' and they look fire in even our giant Isabelle Dome Hat. The hat is basically a gigantic bowl with a long trailing ribbon as a chin strap, which, in theory, should consume their said tiny face, but, because of their personal style, they can pull it off."

Your actual height is important, too

Your actual height is another important factor to keep in consideration, according to Behida Dolic, the milliner behind some truly incredible hats (and dresses, too). For example, the length of the brim should correlate to how short or tall you are. "Height is an important consideration when picking a hat," she says. "Petite women look better with smaller brims. If you are five-foot-two, I would say you should not wear a hat with a brim bigger than four inches. Proportionally, it just looks better if the brim is not too large."

Get your head measured

Knowing your hat size is an extremely important factor in ensuring you find your perfect hat. "Don't overlook the importance of fit; get your head measured and know your size," says Rachel Van Dolsen, CEO and founder of RVD Communications (and self-proclaimed hat lady). "Even the most amazing hat will look weird if it's the wrong size. But, if you have to choose loose or tight, go loose and style it accordingly."

Start with neutrals

The sight of a neon orange hat with a ginormous brim will, for certain, intimidate the hell out of a hat newbie. That's why Van Dolsen suggests starting with neutral colors, first. "Start your hat journey with a classic straw, taupe, brown, or black hat; you can go crazy once you've got fit and style down pat."

Chin straps are cool and functional

For larger hats (or any hat that has the potential to fly off of your head with a small gust of wind), chin straps are key. It doesn't hurt that some of the season's coolest hats have them. "They're easy and practical," says Dolic. "And, when you don't want to wear them, you can always hide them inside of the hat. Also, they can be tied underneath your hair in the back and across the bun on your hair for a bit of an accent. This will keep your hat interesting without overkill."

IRL experimentation is key

While all the factors above can affect what hats look best on you, you'll never really know until you try them IRL. Alyssa Coscarelli, freelance writer and editor, feels that experimentation is key. "Hat shops or vintage shops are a great place to do it! See what feels most 'you,' and then go for it."

When you're experimenting IRL, make sure you're looking your most "everyday you," in order to truly see what suits you. "For anyone who's intimidated and shopping IRL, they should make sure their hair is done how they like it best, and if they do any sort of facial hair or eyebrow maintenance, that should all be taken care of before hat shopping takes place," says Bagtazo. "Same goes for any makeup routine. I say this because you want to see your face under the hat, so your face should look as accurate as possible whilst shopping. Hat shopping after an exercise class, if you're normally a full-coverage-makeup person, is going to turn you off."

Online hat shopping can be tempting, but can also be disastrous unless you know what really works for you (and your head size). "When—and only when!—you've figured out sizing and what styles tend to work best on you, you can dip a toe into online hat shopping," says Van Dolsen. Duly noted!

Build your look around the hat

Recognize that hats can be powerful, so don't be afraid to make yours the key focus of your look. "Don't be afraid of styling an entire outfit around a hat—I do it all the time, and sometimes those end up the strongest looks," says Coscarelli. "Of course, you can always add a hat to your look as a finishing touch, but I tend to have more luck when I style the actual outfit around the hat to let it really shine."

Your hat should feel like it belongs on your head

Simply put, your new hat should feel like it belongs on you. "There are many other elements when it comes to picking a hat, but the one that you should pay the most attention to is that, when you put it on, it feels like it has always been there," says Dolic. "You just know it feels right and belongs on your head. I believe that a perfect hat is the one that fits your style and blends with your personality, but does not take over."

Just stop giving a shit

Here's the thing, while face shape, height, hair cut, etc. can certainly make a difference in finding what sorts of hat will flatter you the most, when it comes down to it, the key is to just go for it, especially when it comes to the more unconventional styles and shapes. This holds true especially considering that many of the hats we've seen on the Fall 2019 runways are pretty out there in terms of design. (I mean, honestly, do you think this Vaquera hat really gives a shit whether or not you have bangs?)

Now that you're ready to try for yourself, what are the biggest hat trends you can you expect to see this season? Well, there are a lot, actually.

For one, the bucket hat is here to stay. "I think the bucket hat will still be going strong, but I expect to see it in some fun new fabrications like wools, plaids, animal prints, and even shearlings and faux furs," says Coscarelli. Additionally, Dolic things easygoing and effortless will be major, but with a hint of surprise. "My major focus this season is on simple Annie Hall-style hats, bucket hats, and 1960s Brigitte Bardot hats in beautiful colors with chinstraps and accents—in fact, most of the details are in the chinstraps," she says. "While the hats themselves are simple and elegant, [the chinstraps] are the elements of surprise."

While wide-brimmed, shallow-crowned hats have been king for the past few seasons, Bagtazo believes "less ostentatious" styles are catching on. "I made a lot of brimless hats for Fall 2019, and even brought a Fez cap into the mix, which I'm pleasantly surprised has been very well received during previews," she says. "Of course, berets are going to be out there, but I'm thinking hat people will rock pillbox-type hats and smaller hats in general."

However, some of the runway's most statement-making hats don't really fit into any category; it was kind of a free for all, and the more quirky and out there, the better. To put it simply, anything goes this upcoming season, as long as you're game for it.

Below, we round up the hats we have our eyes on for Fall 2019 that hat people—seasoned and newbies—should be adding to their shopping lists.

Photo courtesy of Bagtazo

Bagtazo, Jagger Hat, $299, available at Bagtazo.

Photo courtesy of Lack Of Color

Lack Of Color, Ivy Beverly, $149, available at Lack Of Color.

Photo courtesy of Clyde

Clyde, Jeanie Wool-Felt Hat, $248, available at Clyde.

Photo courtesy of Mango

Mango, Shearling Bucket Hat, $29.99, available at Mango.

Photo courtesy of Bona Drag

Yestadt Millinery, Black Peaks Hat, $350, available at Bona Drag.

Photo courtesy of Behida Dolic

Behida Dolic, Cass, $650, available at Behida Dolic.

Photo courtesy of Bagtazo

Bagtazo, Pillbox, $220, available at Bagtazo.

Photo courtesy of Eugenia Kim

Eugenia Kim, Alexa Hat, $78, available at Eugenia Kim.

Photo courtesy of Lykke Wullf

Lykke Wullf, Safari Hatt Fall, $130, available at Lykke Wullf.

Photo courtesy of Bagtazo

Bagtazo, Anna Pillbox, $220, available at Bagtazo.

Photo courtesy of éN Hats

éN Hats, Leopard Bucket, $325, available at éN Hats.

Photo courtesy of Sensi Studio

Sensi Studio, Cap, $138, available at Sensi Studio.

Photo courtesy of & Other Stories

& Other Stories, Corduroy Bucket Hat, $39, available at & Other Stories.

Photo courtesy of éN Hats

éN Hats, Round Curvy in Red, $230, available at éN Hats.