Choosing a Hat for Your Face Shape

Four Two Roads men's hats for smaller heads stacked atop one another in white, brown, green, and black

Let’s talk about hats, yeah? The most formidable accessory you can have at your disposal. Hats are great for when you want to elevate your style—or when you want to hide a bad hair day. 

If you’re shopping around for the first time, choosing the right hat can feel impossible. Today we’ll focus on how to choose hats for face shape, hats for men with heads big and small, and hats for different hair and body types. If it has to do with hats, we’re on top of it.

Four Two Roads men's hats for smaller heads stacked atop one another in white, brown, green, and black


Styles by Head Size

Hats for Men With Smaller Heads

For men with smaller heads, fit is everything. To avoid being overwhelmed by a hat's size, opt for men’s hats for smaller heads that are proportionate to your head. 

Try these styles: 

  • Beanies: While beanies are known for being the perfect fit for cold-weather climates, beanies can be a stylish addition to casual outfits. Look for beanies that sit snugly on your head to avoid a slouchy appearance (unless that’s the look you’re going for, of course).
  • Flat Caps: Flat caps or newsboy caps are great choices for smaller heads, though harder to come by nowadays. Their close-fitting design can complement your facial features without overwhelming them, which is important when considering hats for men with smaller heads.
  • Short-brimmed hats: A sleek short-brimmed hat can keep your look simple yet stylish, frame your face nicely, and give you a larger presence without an overwhelmingly large brim.


Hats for Men With Larger Heads

If your head is on the larger side, the fit is still top of mind, but comfort is likely what you’re looking for. If a hat is too tight, you’ll probably deal with headaches (and then you’ll associate hats with headaches).

Here are the best hats for men with big heads:

  • Ball Caps: The great thing about ball caps is that they’re inherently adjustable. Keep your eyes out for adjustable straps and snapback closures so you can customize the fit to your head size and shape.
  • Wide-Brimmed Hats: Broad brims (like those found with rancher or most pencil-brimmed hat styles) will balance out the proportions of your head and add an air of sophistication to your look. Plus, wide-brimmed headwear is known to be comfortable and effortlessly stylish, arguably a great beginner hat.


Styles by Head Shape

Different Two Roads men’s hats for smaller heads stacked atop one another

Do you know your head shape? There are lots of guides online that you can refer to before continuing on your quest for new accessories. The right hat will not only complement your face shape but can enhance your overall appearance and style (and your confidence in turn). 

Let’s see what some of the best hats for face shape are:

  • Round Face: If you have a round face, opt for hats with angular shapes to add definition. Fedoras or trilby hats with a pinched crown are the best hats for round faces because they can create the illusion of lengthening your face.
  • Square Face: For a square face shape, try hats with soft lines to balance out the sharp angles of your face. Bucket hats or ball caps can soften your features and create a harmonious look.
  • Oval Face: With an oval face shape, most hat styles will suit you well. Experiment with different hat designs to discover what suits your personal style best.
  • Heart-Shaped Face: If you have a heart-shaped face with a wider forehead and a pointed chin, opt for hats that balance your facial proportions. Try out pork pie hats, classic fedoras, or styles with medium brims.


Styles by Hair Length

Hats for Bald Men

If you’re rocking the bald look, hats can serve both as a style statement and protection from the elements. Consider baseball caps or hats with brims since they offer excellent sun protection for your scalp while keeping stylish. Or, you could try a beanie if you’re after warmth with a casual, effortless vibe. The great thing about these hats is that they come in an array of colors, styles, prints, and textures, so you’ll have ample opportunity to find one you vibe with.


Hats for Men With Long Hair

Hair in itself is something of an accessory and can drastically change your overall appearance. That’s why some hat styles work better with longer hair, shorter hair, or no hair at all. If you’re looking to accentuate your long-locked look, don’t be afraid of Western hats. This style is a fantastic option for men with long hair with their laid-back, bohemian energy.



Two Roads Has Hats for All Head Shapes and Sizes

A man modeling a hat for men with big heads from Two Roads

Find your perfect fit from our collection of high-quality men’s hats. Get to know your features and experiment with different styles to find out what you like (and what you don’t). By investing time and energy into your accessories, you’ll discover how to authentically enhance your unique style.

Whether you have a smaller or larger head, a round or square face, or sport long hair or no hair at all, there’s a hat for face shapes like yours at Two Roads that marries fashion with function. We invite you to explore our catalog of elevated men's hats as you evolve your personal style and hope you enjoy implementing new looks into your rotation.

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