The Best Hats for Every Face Shape

Flat cap? Fedora? Boater? We're here to help.

March 24, 2021 1:16 pm
It's time to find out what hat is best for you?
It's time to find out what hat is best for you?
Mr Porter, Nordstrom, Saks 5th Avenue

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So, you’re sick of the regular ol’ baseball cap and ready to explore your options when it comes to other styles of hats. Maybe this sudden interest was spurred by one Bradley Cooper’s recent public appearances in which he was spotted sporting a flat cap (backwards, we might add), or maybe you’re just looking to add a little variety to your life in the form of some new headwear. But before you go out and start splurging on beanies, boaters and bucket hats, allow us to stop you before you make a regrettable and ill-informed purchase, because as sad as it may be, not all hats are universally flattering.

Much like any other article of clothing or accessory, hats aren’t all going to fit or look the same on everyone, so as great as that flat cap might look on Mr. Cooper, we can’t guarantee it’ll have the same effect on you. Below, a guide to finding the best hat for you, from figuring out your face shape to determining the hat styles that will work best with said shape.

Determining Your Face Shape

Before finding what hat works best for you it’s first important to determine what face shape you have. For those looking to be precise, you can take a flexible tape ruler to measure your forehead, cheekbones, jawline and face length, or if you feel comfortable enough eyeballing it, simply to take a gander to the closest mirror or reflective surface and make an educated guess based off the descriptions below.

Naturally, not everyone’s face is so easily categorized, with some featuring an amalgamation of characteristics from different shapes or a hybrid of two, but even being able to note these features will be helpful when it comes time to choose a hat.

Jake Gyllenhaal Oval Face Shape
Jake Gyllenhaal
David M. Bennett / Getty


Generally considered to be the most blessed of face structures due to being so proportional, if you have an oval shape then your forehead is slightly wider than your chin and your jaw narrower than your cheekbones. Celebrities with oval faces: Jude Law, Jake Gyllenhaal and Idris Elba.

Leonardo DiCaprio Round Face Shape
Leonardo DiCpario
Jeff Kravitz / Getty


When it comes to round faces the length and cheekbone measurements are nearly the same, the face largely characterized by its softer angles and fuller cheeks. Celebrities with round faces: Leonardo DiCaprio, Kanye West and Jack Black

Ryan Gosling Heart-Shaped Face
Ryan Gosling
Jeff Kravitz / Getty

Heart/Inverted Triangle

If you find your forehead measurements greater than those of your cheekbones and jawline, and have a chin that comes to a point, then your face is heart-shaped, also referred to as an inverted triangle. Celebrities with heart-shaped faces: Ryan Gosling, Ryan Reynolds and Joseph Gordon-Levitt

Keith Urban Triangle-Shaped Face
Keith Urban
Patrick Riviere / Getty


Where heart-shaped faces are an inverted triangle, pear-shaped faces are just regular ol’ triangles — the face is typically defined by a strong jawline that is slightly wider than one’s forehead. Celebrities with pear-shaped faces: Keith Urban, James Corden and Taylor Lautner.

Cillian Murphy Diamond-Shaped Face
Cillian Murphy
Jason Mendez / Getty


The most noticeable aspect of a diamond-shaped face tend to be the cheekbones, which will protrude past one’s forehead and jawline, thus creating a “diamond” effect that’s further emphasized by a pointed chin. Celebrities with diamond-shaped faces: Robert Pattinson, Cillian Murphy, Christian Bale.

Brad Pitt Square Shaped Face
Brad Pitt
Steve Granitz / Getty


Typically with a square face shape you’ll find the width of your jaw, forehead and cheekbones to be the same or nearly the same width, with strong, definitive angles. Think of it as similar in shape to a round face, just slightly more chiseled. Celebrities with square faces: Brad Pitt, Elijah Wood, David Beckham.

Henry Cavill Oblong-Shaped Face
Henry Cavill
Andreas Rentz / Getty


Sometimes referred to as rectangular shaped, oblong faces bear some resemblance to those that are square shaped, most notably in regards to the strong jaw, yet differ in that they are longer than they are wide. Celebrities with oblong faces: Henry Cavill, Ben Affleck, Matt Bomer.

Best Hats for Oval Faces: Bucket, Flat Cap

As we mentioned before, if you find yourself with an oval-shaped face, consider yourself lucky, as pretty much any hat will work well with your face. With that being said, use your structure to your advantage and experiment with styles that are slightly harder to pull off, like a bucket hat or the notoriously difficult flat cap, both of which offer two varying yet distinct styles.

Because oval faces can at times appear a bit long, it’s best to avoid hats that feature tall crowns (i.e. a cowboy hat), as they’re likely to accentuate the length of your face.

Nanamica Gore-Tex Bucket Hat in Khaki
Mr Porter

Nanamica Embroidered GORE-TEX Bucket Hat

Lock & Co Hatters Nylon Flat Cap in Navy
Mr Porter

Lock & Co Hatters Nylon Flat Cap

Best Hats for Round Faces: Fedora, Trilby

In order to combat the softness of a round face, it’s best to seek out hats with sharp, defined angles that will allow for some contrast. Fedoras and trilby hats are ideal thanks to their angularity, especially when worn at a slight tilt.

Despite in recent years the attribution of the fedora to “m’lady” types or insufferable hipsters, the style they’re typically wearing is actually a trilby, which is noted by its smaller brim, bowl top and subtly pinched creases. But don’t allow these stereotypes to prevent you from trying out the hat for yourself — just be wise to avoid ones patterned with pinstripes (trust us). Instead, opt for one in a lighter and much more casual material, like Paul Smith’s straw trilby hat below, perfect for the approaching warmer months.

In turn, fedoras should more appropriately be associated with the likes of jazz musicians or Humphrey Bogart in Casablanca, the wider brim usually turned down to help shade the eyes and create an air of mystery.

Brixton "Messer II" Felted Wool Fedora

Brixton “Messer II” Felted Wool Fedora

Paul Smith Multi-Tab Straw Trilby Hat
Saks 5th Avenue

Paul Smith Multi-Tab Straw Trilby Hat

Best Hats for Heart-Shaped Faces: Boater, Cowboy

For those with a heart-shaped face, you’re going to want a hat that will help to detract from the width of the forehead, so something with a small to medium brim that will cut across the forehead, much in the way a boater or cowboy hat would.

While we understand a hesitancy in approaching these styles for fear of looking too costume-y or posturing as something you’re not (say a rugged cowboy when you’re in fact a born and bred city boy), there are variations of these styles that are less literal yet still give the benefit of highlighting your bone structure.

Yet if you really can’t bring yourself to commit to these more ostentatious silhouettes, a classic baseball cap will help to balance the width of the forehead with the rest of one’s face.

Borsalino The Boater with Woven Straw in Red

Borsalino The Boater with Woven Straw

Wyeth McGraw Cowboy Hat

Wyeth McGraw

Best Hats for Pear-Shaped Faces: Panama, Wide Brim Fedora

Much like oval faces, pear, or triangle, shaped faces are capable of working with a range of hats. However, if you’re at all concerned about your jawline looking too prominent, you’ll want to veer away from hats with too narrow of a brim and opt instead for one wide enough to balance out your shoulders. In this instance, you can go for something subtle like a Panama hat with a medium brim and small crown, or something even on the wider side, like Lack of Color’s Zulu Rancher below.

Simons White Authentic Panama Hat

Simons White Authentic Panama Hat

Lack of Color Zulu Rancher Wide Brim Fedora
Lack of Color

Lack of Color Zulu Rancher

Best Hats for Diamond-Shaped Faces: Beanie, Outback

When it comes to a diamond-shaped face, the placement of the hat is nearly as important as the hat itself, especially in regards to the more narrow forehead of the face. Taking this in consideration, it’s important to choose a hat that can easily be adjusted, whether sliding it forward or backwards (like a beanie would allow) or one with a more malleable brim like that of an Outback-style hat, which tips forward in the front to help disguise the forehead and thus highlight the cheekbones.

UO Short Circular Roll Knit Beanie in Pink
Urban Outfitters

UO Short Circular Roll Knit Beanie

Tenth Street Albuquerque Outback Hat
Tenth Street

Tenth Street Albuquerque

Best Hats for Square Faces: Newsboy, Fisherman

To bring some softness to the sharp angularity of a square face, we recommend a hat that’s a little less structured and offers more in the way of soft curves and edges. While similar to a flat cap, a newsboy hat offers slightly more volume in fabric on the top, creating less of a straight and narrow line and instead sloping in a curve towards the face.

Similarly, something along the lines of a fisherman’s cap will work thanks to its circular shape and rounded brim, which hangs just slightly over the edge of ones forehead while still allowing for the strong facial features to shine through.

G-Star Raw Riv Hat Newsboy Cap in Navy

G-Star Raw Riv Hat

Brixton Fiddler Fisherman Cap in Black

Brixton Fiddler Fisherman Cap

Best Hats for Oblong Faces: Western, Dad Hat

To help further prevent elongation when it comes to the often already lengthy oblong/rectangular faces, a hat that sits lower on the forehead further aids against the appearance of extra length. Styles like the Western-inspired silhouettes of Stetson and even the classic “dad” cap are useful in their ability to cover much of the forehead while also managing not to add too much height.

Stetson Langston Hat Huckberry Exclusive

Stetson Langston

Corridor New York New York Cap Baseball Hat in Navy

Corridor New York New York Cap

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