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Reasons You Might Not Look Good in a Hat

By Taylor James


Updated on

Hats are a wonderful accessory, especially on bad hair days; not only will a hat cover-up bedhead, but it can be an excellent addition to an outfit. They’re also great for sunny days when you want to be outside but need some shade. If you desperately want to wear hats but can’t seem to pull them off, there’s probably a simple reason why.

You might not look good in a hat because it doesn’t flatter your face shape or hairstyle. Your face shape is a critical factor to consider before choosing a hat, as some styles can emphasize facial features. How you wear your hair will also affect how you look and how the hat sits.

The rest of this article will discuss why your face shape, hair, and overall style are essential to looking good in a hat. We’ll also get into how to determine your face shape and which hats best suit which face shapes. Lastly, we’ll cover which hairstyles might flatter your hat more.

Hat over eyes

The Hat Doesn’t Flatter Your Face Shape

Everyone has different shaped faces and depending on yours, the hats you wear might not work well. You might not be able to put your finger on it, but it just doesn’t seem to work. 

For example, if your face is round and short, and you wear a hat that hides half of it, it probably won’t look too good. Choosing a hat that brings out the positive features in your face is what will make the hat a must-have accessory.

Let’s figure out the shape of your face and what hat will suit you the best.

How To Determine Your Face Shape

There are seven basic face shapes:

  • Long/rectangular
  • Round
  • Square
  • Heart
  • Oval
  • Diamond
  • Pear/triangle. 

Determining the shape of your face might be a little tricky, especially since there are so many basic shapes. However, with a bit of measuring and sometimes staring at yourself in the mirror, it shouldn’t be too difficult.

It’s essential to remember that everyone’s faces are different, so not everyone will fall exactly into one category. Some measurements might be a little off depending on the person, but finding the shape that is close enough measurement-wise will work wonders.

The first thing you’ll want to do is measure your forehead, cheekbone, and jawline width. Then, measure the entire length of your face. 

  • Long/rectangular-shaped face. People with long or rectangular-shaped faces will have a forehead around the same width as their jaw. The face will be significantly longer than wide, and the jawline will be prominent and squared.
  • Round-shaped face. People with round-shaped faces will typically have rounded hairlines, and the length and width of their faces will be about the same. The jawline won’t have any strong angles or be a prominent facial feature.
  • Square-shaped face. People with square-shaped faces will have a hairline that is essentially a straight line, and the cheekbones will be so minimal that they’re difficult to point out as the face is more of a straight line. The jawline will be strong and squared.
  • Heart-shaped face. People with heart-shaped faces typically have a widow’s peak, meaning their hairline becomes V-shaped at the middle of their forehead. The forehead will also be wider than the jawline, and the jawline will come to more of a point.
  • Oval-shaped face. People with oval-shaped faces will have longer faces with broad cheekbones. The forehead will be taller and usually smaller than the face’s width. The jawline won’t have any sharp angles.
  • Diamond-shaped face. People with diamond-shaped faces will have a forehead width and jawline that is smaller than the cheekbones. The face’s length will usually be around the same size at the width.
  • Pear/triangular-shaped face. People with pear or triangular-shaped faces will have a wider jaw line than the forehead’s width. It’s essentially the opposite of the heart-shaped face.

Which Hats Look Best With Which Face Shape?

Now that you have a good idea of your face shape, let’s look at some hats that flatter each. There are many more hat styles, but we’re only going to discuss the most common types you see today with each shape:

  • Long/Rectangular: This face shape will look best with hats that make the head appear shorter, such as wide brim hats or cowboy hats.
  • Round: This face shape is shorter, so hats that elongate it will work best, such as a beanie or fedora. Go here for some examples of hats that work for round face shapes.
  • Square: This face shape is very angular, so floppy or wide-brim hats can soften those features. Read more and see examples here.
  • Heart: The face shape will look best with a baseball cap or even a wide brim hat.
  • Oval: This face shape is the most commonly seen, and it goes with any hat style.
  • Diamond: This face shape will work best with short-brimmed hats or beanies.
  • Pear/Triangular: This face shape will benefit from baseball caps and fedoras. See examples here.

If you’ve worked out your face shape and you still feel like your hat isn’t a good fit, it could be that you’re not styling your hair right.

You’re Styling Your Hair Wrong

The way you style your hair with a hat might be a reason why you don’t look good in them. This typically only matters for people with longer hair. 

The style you choose is essential to consider with your face shape, so styling your hair in a way that doesn’t flatter you can look bad.

Different hairstyles flatter different hats. For example, most people look best with their hair in a low bun or ponytail while wearing a baseball cap, while a wide brim hat might look better with the hair down. However, this also greatly depends on the shape of your face.

Remember that a high pony or messy bun might look great on a hatless day, but it will stick out under a hat. Similarly, pulling your hair back can be quite harsh, so consider pulling a few strands of hair to the front to frame your face.

You’re Wearing the Hat Wrong

Believe it or not, you can wear a hat incorrectly. While it definitely goes on your head, there are different ways you can style a hat or angle it to make it look better on you.

For example, you can wear a baseball cap backward if that better suits your face, or try angling a wide brim hat or fedora up or down, depending on the look you’re going for and your outfit.

The Hat Doesn’t Match Your Style

Considering your overall style in clothes is essential when choosing a hat that looks right on you. If you’re trying to wear hats that clash with your style, it will look weird. Therefore, it won’t look any good.

In general, if you wear a lot of loud colors and patterns, a colorful or patterned hat probably won’t look good. The same thing goes for the opposite situation—if you wear many neutral colors, a more colorful hat can accentuate your outfit.

While there are general rules or guidelines, there are also hats that just look good with specific styles. For example, if your style is more bohemian, wide-brim hats or fedoras will work well with most outfits.

However, if your style leans more toward casual, a baseball cap or even a beanie would work well. It all depends on your specific style and which hats blend with that style.

Final Thoughts

To look good in a hat, you need to determine which style of hat best suits your face shape and overall style. Trying to style the hat differently, picking a hat that matches your overall aesthetic, and changing your hair are all ways that could improve the way a hat makes you look.

While finding the right hat for your face shape is a good suggestion, it all comes down to confidence. Feeling confident and comfortable in what you’re wearing will make you look good, and that’s all that should really matter.

About Taylor James

As Philip Treacy once said, “How a hat makes you feel is what a hat is all about.” And on that note, I hope you enjoy your hats and find the site useful. Learn more about Hat Realm's Editorial Process.