If you want to wear a hat, but aren’t sure how to choose one that’ll look good, this guide will help.

So, you’ve decided that you want to start wearing hats. You know that some look better on you than others but you may not understand why or even what the options are. Here’s a guide to help you find the perfect hat to top off your wardrobe.

This article will focus more on what components and styles flatter your face shape and how you can minimize features you don’t particularly like by wearing certain styles.

Parts of a Hat

Let’s start with a quick refresher on hat anatomy.

The crown is the upper part of the hat that’s attached to the brim.

The hat band covers the intersection.

The crown can have a crease down the middle with dents or dimples at the two sides. The crown can be tapered or straight and there can also be a taper that narrows the crown.

Brims can be curled up (completely around, or just the front or back), or snapped down. You always have the option to leave the brim as it was designed.

Also, keep in mind that hats can be tilted to one side, tilted forward to cover more of your face, or backward to open your face up.

Sizing Your Hat

Your first hurdle is to make sure that you’re buying the right size hat.

Sizing can be either in centimeters, inches (the US and United Kingdom have separate sizing), or the small-medium-large scale.

Each manufacturer using this scale sizes them a bit differently so check their chart.

To find your hat size, measure your head using a flexible tape measure from the mid-forehead just above the ears to the back of the head. You don’t take this measurement parallel to the ground — it’s angled.

Matching Hat Styles to Face Shapes and Features

The next obstacle is determining your face shape which is based on the relative measurement and placement of your forehead, cheekbones, jawline, and overall length.

If you’re not sure or want to double-check what face shape you have, this site will help. Even though it may be an optical illusion, hats can help your face look more balanced and create a sense of harmony and symmetry.

Oval Faces

Oval face shapes are much like blood type O…most hat styles will look good. The only exception is wearing very round crowns with narrow brims such as bowler hats.

These will add too much roundness to your face and may end up looking costumey.

Oblong or Rectangular Faces

The goal for oblong or rectangular faces is to shorten their appearance by adding width and balance. In this case, you want to tilt your hat to one side and pull it down to your eyebrows. This minimized the vertical structure of your face.

Tall crowned hats with narrow brims only elongate your face more so look for shorter, non-squared-off crowns. You want a brim that’s wide, sits at the center of your forehead, or just below your eyebrows.

Much like wearing a wide band of contrasting color across your waist, having a wide contrasting band will make your face look shorter.

Flattering hat styles include large-brimmed fedoras, cowboy hats, and sunhats.

Trapper and Peruvian hats create more width visually and keep you warm.

Heart-Shaped Faces

People with heart-shaped faces have a broad foreheads, wide cheekbones, and a narrow, sometimes pointy chin and need to balance their forehead and chin.

This can be done using a medium-sized hat with a prominent crown such as fedoras and homburgs.

A wide brim will only accentuate the disparity between the forehead and chin (an inverted triangle), so avoid straight brims. Look for medium-brimmed hats that are upturned to draw attention to the eyes, not the forehead.

Slanting your hat to one side will also draw attention to your eyes and slim your face. Beanies, baseball caps, and newsboy caps are also good choices.

Triangular/Pear-Shaped Face

A triangular/pear face is the opposite of heart-shaped with a wider jawline, smaller cheekbones, and a narrower forehead. Your goal is to create more length, but overall, your hat choices are similar to those with oval faces.

More complimentary choices include high crowns that are narrower than your cheekbones with a small brim (worn either straight or upturned).

Adding something to the hat band will create an asymmetrical effect.

You can also pull off beanies and berets since they’ll shorten your forehead.

Round Faces

If you have a round face you want to add height and asymmetry to distract from round facial curves. Your goal is to create angularity.

One way to do this is to tilt your hat back from your face. If you tilt it forward, you’ll make yourself even shorter.

You can add height by wearing medium to high hats with a slight taper drawing the eye upward even more.

Avoid round crowns (derby hats). Your brims should be moderate to wide.

Like tilting the hat back, you can turn the brim up but don’t snap it down.

Another way to add height is to have a narrow hat band in a contrasting color.

Hat styles that will flatter a round face can include fedora, gambler (cowboy), Panama, newsboy, baseball hats, and beanies.

Make sure that you don’t wear hats that have narrow brims, round crowns, are too small, or any style that sits too low over the forehead. You want to open your face and add angularity.

Square Faces

Square faces have the opposite problem as round faces — you need to soften the edges of your face and add some curvature so you look less boxy.

Look for rounded, circular features with curving lines, i.e., round and curved medium-height or full and round crowns.

Brims can be large, wide, and soft, and be upturned or fully snapped.

Tilting the hat will break up the symmetrical lines of your face. Don’t however, tilt your hat back — this exposes your face more.

You have many hat styles to choose from including the homburg, bowler, sunhat, cowboy, or beret.

Just avoid hats with short to no brims or anything with severe angles that will accentuate sharp features.

Diamond-Shaped Faces

Diamond-shaped faces are wider around the top part of the head with a narrower jawline. How you wear the hat is as important as what you wear. Wear hats further back on your head so you don’t shorten your face.

Hats like pork pie and trilby hats with shallow crowns work well.

Large Ears

Moving along from face shapes — sometimes, there is a particular facial feature that you want to minimize. The right hat can help you do that.

Many men are self-conscious of their prominent ears. You want a hat that helps cover them so look for wider brims that are snapped down, not up.

Actually, you want to avoid anything that’s upward-facing and pointed. Small hats with short brims just accentuate your ears so look for full and moderately tall crowns.

Styles that will work are wide-brimmed gambler, fedora, cowboy, or Panama hats. You can either leave the brim straight or fully snapped and tilt the hat down in the back.

Receding Chin

If you have a receding chin you want to draw attention upwards. Medium-crowned hats such as porkpie, trilby, and fedoras (medium brimmed) that have a slight pinch that isn’t too pointy, yet not round will work.

You can also tilt the hat and snap the front a bit. Avoid very large hats with tall crowns because these will actually accentuate a receding chin. The hat band should be proportionate, so narrow.

Long Nose

Long noses can happen with any shaped face. You want your hat to break up the line from the brim to the tip of your nose so choose a hat with a medium crown that isn’t pinched too tightly at the front.

You don’t want the crown to taper upward. Choose a wide and colorful hat band and have the brim extend beyond the top of your nose.

Tilting it to the side will further draw the eye away from the center of your face. Fedoras are a good choice.

Prominent Jaw

If you have a prominent jaw, you need a hat that will add more balance to your face. High and full crowns are too heavy so look for low to medium-high crowns with side dents to add fullness.

Having the crown taper toward the top also helps draw the eye up. A medium-width brim that is snapped down is a good choice but make sure your brim isn’t turned up in the back. A slight side tilt also balances out a prominent jaw.

Other Considerations

Finally, you have to realize that your head is attached to your body, and wearing a hat impacts your overall look.

Small hats with narrower crowns and short brims automatically make a person look bigger. If you’re already large, avoid these. By wearing a larger crown/brim, you will look more proportional.

Adding a hat band that’s wider and low contrast to the hat color, as well as a slight pinch, will help. Snap a brim, that’s at least 2 ½”, down. Fedoras and Homburgs are good style choices.

If you are short and slim, draw the eye up, but don’t let your hat overwhelm you. Look for a tightly pinched medium crown.

Keep the brim under 2” and curl it up or sideways (never snapped down) to draw the eye upwards. Wide brims and really tall crowns will actually make you look shorter.

If you’re tall and thin, you may not want to accentuate your height, so avoid high crowns. Use a contrasting hat band to visually separate the top from the bottom of the hat.

Keep the brim around 2”, snap it down, and tilt it to one side for a more elegant look. Short-brimmed hats that are curled up will make you look taller.

Final Thoughts

Hats can cover up a multitude of imperfections. Of course, you should wear what you like and what you think flatters you, but understanding some of the basic principles of how different structures affect different face shapes will help you choose a hat that you can wear with confidence.

For a discussion of different hat styles see our guide to wearing hats.

Questions? Comments? Leave them below!