in: Accessories, Featured, Style

• Last updated: September 25, 2021

The Perfect Hat For Your Ugly Mug

Vintage men wearing hats.

What humans find attractive is largely based on symmetry. The more symmetrical a face is, the more appealing it appears to others. But there’s not much we can do, short of surgery, to change the symmetry of our faces. There are ways to mitigate our asymmetries, however. You may have heard a woman in your life talk about getting a haircut that flatters her particular face shape. While dude’s haircuts don’t come in enough varieties to have the same effect, there is another way guys can balance out their faces: hats. All hats make a man look more dapper. But picking a hat that is right for your face shape will increase your attractiveness and give you a sharper appearance. If you’ve been inspired to bring back the hat, but weren’t sure what kind of hat to get, this guide will help you pick the right hat for your ugly mug.

Anatomy of a Hat

Before we get started, let’s do a quick rundown of some of the terms we’ll be using to fit a hat to your mug.

The anatomy of hat.

“Taper” describes how narrow the top of the crown is compared to the bottom.

Tapered flannel hat.

Here’s an example of a hat that tapers. Notice how it gets narrower near the top of the crown.

White straw with black band hat.

Here’s a hat that has no taper. Notice how the crown doesn’t narrow as it gets to the top.

Now let’s match a hat to that ugly mug of yours:

Short, Full Face

Jack Black portrait.

Your face is shaped like: Jack Black

A round face tends to look short, so you want a hat that will give you a little height.

Crown: Medium height and size

Taper: Slight

Hat Band: Narrow band of a contrasting color will add height

Brim: Moderate width. Snap the brim to its full width and turn it up. Never snap it down or it will make your face appear shorter.

Tilt: Back from face; tilting it over your face will make the face appear shorter.

Recommended hat: Fedora, Gambler, Panama

Long, Thin Face

Will Arnett portrait.

Your face is shaped like: Will Arnett

Look for a hat that shortens the appearance of your face.

Crown: Shorter height. Avoid crowns that are square, full, or too high.

Taper: Moderate

Hat Band: Wide (will make you face shorter) with a contrasting color to break up your vertical lines

Brim: Moderately wide, snapped from ear to ear

Tilt: To the side with a slight back tilt

Recommended hat: Fedora, Homburg, Derby

Top-Heavy Face

Jon Favreau portrait.

Your face is shaped like: Jon Favreau

The top-heavy face is wider on the top half and tapers to a more narrow chin line. You want a hat that will balance the top and bottom out.

Crown: Medium to short height, pinched toward the front. Avoid crowns that are full or too high.

Taper: Moderate taper

Hat Band: Medium to narrow, in a color similar to the color of the hat.

Brim: Medium width, rolled at back and sides, flat in front

Tilt: To the side, and not too far back on the head or you’ll show too much of your wide forehead

Recommended hat: Fedora, Homburg

Square Face

Orlando Bloom portrait.

Your face is shaped like: Orlando Bloom

Pick a hat that will add some curvature to your face and make it appear less boxy.

Crown: Medium height, full and round

Taper: Minimal to non-existent

Brim: Wide width, fully snapped or turned up

Tilt: A side tilt will break up your square face lines. Don’t push it too far back on your head.

Recommended Hat: Homburg, Bowler

Long Nose

Adrien Brody portrait.

Your nose resembles: Adrien Brody, although perhaps not that long

Pick a hat that will break up the line from the brim to the tip of your nose.

Crown: Medium height, and not pinched too tightly at the front.

Taper: Minimal to non-existent

Hat Band: Wide and colorful

Brim: Wide width, you want it to extend beyond the tip of your nose

Tilt: To the side

Recommended Hat: Fedora

Prominent Jaw

Aaron Eckhart portrait.

You’ve got a chin like: Aaron Eckhart

Pick a hat that will balance your strong chin.

Crown: Medium or low height, avoid crowns that are full or too high. Pick one with side dents, this adds just the right amount of fullness.

Taper: Slight

Brim: Medium width, snapped fully across. Make sure it doesn’t turn up in the back sharply or it will make the jaw appear even more prominent.

Tilt: Level, with a side tilt.

Recommended Hat: Fedora

Receding Chin

Paul Dano portrait.

You’ve got a chin like: Paul Dano

Pick a hat that will draw attention upwards, away from the chin.

Crown: Low height

Taper: Significant

Hat Band: Narrow

Brim: Flat, or very shallow snap

Tilt: Level, with significant side tilt.

Recommended Hat: Porkpie, Trilby, Fedora with short crown and brim

Prominent Ears

Will Smith portrait.

You’re ears stick out like: Will Smith

If you ears are large or stick out, pick a hat that will cover them.

Crown: Full and moderately tall

Taper: Minimal to slight

Brim: As wide as possible in order to cover the ears and make them seem smaller. Flat or fully snapped. Do not roll the brim as this will highlight the ears.

Tilt: Down in the back.

Recommended Hat: Gambler, Panama, Wide-brimmed Fedora

The Best Hat for Hair and Complexion

Most hat colors look good on any man. But some go particularly well with certain complexions and hair colors.

The Best Hat Color For Your Complexion

Ruddy: Brown, Blue, Gray

Dark: Brown

Darker Olive: Brown or Green

Pale: Dark Blue, Gray

The Best Hat Color For You Hair Color

Auburn, Red: Brown, Green, Blue

Blonde: Brown, Green, Gray

Brown: Gray, Green

Gray Hair: Green, Gray

Pulling It All Together: Matching Your Clothes with Your Hat

You can wear a hat any old time, with any outfit, of any color. But when you want to look particularly sharp, make sure your hat color complements your suit or outfit.

The Brown Hat

Brown hats look best with brown or green suits or coats. If wearing a dark blue or dark gray suit, a dark brown hat may also look acceptable.

The Gray Hat

Gray hats are quite versatile and can be paired with black, blue, and dark gray suits and coats.

The Blue Hat

Wear a blue hat with a blue or gray suit or coat. If pairing a blue suit with a blue hat, the colors must match fairly closely. Alternatively, you can pair a dark blue suit with a light blue hat or vice versa. You can also get away with wearing a blue hat with a light brown or tan suit.

The Green Hat

Green hats are surprisingly versatile. They look best with tan or light brown suits. But they also accent black, green, and gray suits very nicely.

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