How to Choose the Right Hat for Your Face Shape

Some people are just “hat people” – it seems every shape suits their face and they have an impressive collection of hats to prove it! There are also those who look especially handsome in some hat shapes, but aren’t sure of hat etiquette and so shy away from the whole idea.

If you're shying away from the idea of wearing a hat because you don't know what suits your face shape - we are here to help.  

In this article, we’ll look at hats for men with faces of different shapes: oval, round, oblong and square (find your face shape here!), and consider which hats are best when wearing a suit versus a tuxedo. 

Hats for Oval Faces

Gentlemen with oval faces have balanced proportions that work well with a wide variety of hat styles. The goal when choosing a hat, then, is to enhance the naturally versatile shape of the face without overwhelming or elongating it. 

• Fedora – A timeless classic that suits the symmetry of an oval face. Opt for a medium-brim fedora to maintain proportion and add sophistication.

• Trilby – The shorter brim and angled style of a trilby pairs well with an oval face. For a modern take, wear it at a slightly tilted angle.

• Panama Hat – The Panama complements the balanced features of an oval face. Choose one with a medium-to-wide brim for a relaxed yet sharp look.

• Flat Cap – The low-profile and structured design of the newsboy hat is perfect for oval faces – it adds subtle character without overshadowing the proportions of the face.

Man with an oval face shape, wearing a handsome flat cap

Hats to Avoid for Oval Faces

While most hats suit an oval face, overly tall crowns, like a stovepipe hat, can make the face look unnaturally elongated. Similarly, hats that are extremely tight or sit too low on the forehead may throw off the natural balance.

Hats for Round Faces

For men with round faces, the goal is to create the illusion of length and add definition to the face. The best hats for round faces are those that add angles, height, or structure. 

• Fedora – The high crown and angled brim of a fedora helps to elongate the face and add sharpness to softer facial features. Opt for a medium-to-wide brim, as a narrow brim can emphasize the roundness of the face.

• Trilby – With a shorter brim than the fedora, the trilby adds height and definition. Wearing it tilted slightly to one side creates more angles.

• Panama Hat – This wide-brimmed, structured hat adds balance and sophistication while offsetting the roundness of the face.

• Flat Cap – A flat cap that is slightly snug is best. Avoid overly bulky styles, as they can overwhelm the face.

Man with a round face wearing a trilby hat

Hats to Avoid for Round Faces

Any hat that lacks structure or height will not provide balance. A wide, rounded crown – such as that of a bowler hat – mimics the shape of a round face and can make it appear fuller. Hats with a downward-sloping brim, such as a bucket hat, can accentuate roundness.

Hats for Oblong Faces

Men with oblong (longer, rectangular-shaped) faces should focus on hats that balance the face’s length and create the illusion of width. The right hat can shorten and soften the face, helping to achieve a well-proportioned look. 

• Fedora – A fedora with a wide brim and medium to low crown helps balance the length of an oblong face. Avoid tall crowns, as they add unnecessary height.

• Wide-Brim Hats – Sun hats, Panama hats, and boater hats with wide brims draw attention outward, rather than upward, creating the illusion of a shorter face. Look for structured or slightly rounded designs.

• Flat Cap – Flat caps sit low on the head and add horizontal lines that juxtapose the length of the face, offering a sophisticated, casual style that complements oblong faces.

• Bowler Hat – The rounded crown of a bowler hat adds width and softness to the face’s elongated shape. Stick to versions with shorter brims to maintain balance.

Man with an oblong face shape, wearing a bowler hat

Hats to Avoid for Oblong Faces

Avoid styles with exaggerated or tall crowns, such as stovepipe hats or certain fedoras. Narrow-brim hats emphasize the vertical lines of the face, making it appear longer. Slouchy beanies and oversized hats can accentuate the elongated shape of an oblong face.

Hats for Square Faces

Gentlemen with square faces tend to have strong, angular jawlines and broad foreheads, so the goal when choosing a hat is to soften the angularity and add a touch of curve or height. The ideal hats will be proportionate and have rounded elements. 

• Fedora – The structured crown and medium-to-wide brim of a fedora create contrast with the sharp angles of a square face. A slightly curved brim softens the strong jawline, while the crown adds height.

• Trilby – The shorter brim and angled style adds sophistication and helps balance square proportions. Tilt it slightly for a more dynamic, softer look.

• Round-Crown Hats – Hats with rounded crowns, such as bowler hats or cloches, counterbalance the angular features of a square face. The rounded shape provides a softening effect.

• Wide-Brim Hats – Sun hats, Panamas, or safari hats with wide, curved brims create the illusion of length and soften the edges of the face. Avoid overly stiff or flat brims to maintain a harmonious look.

Example of a man with a square face wearing a boater hat - a hat you should avoid

Hats to Avoid for Square Faces

Avoid boxy or angular hats with overly structured, sharp lines, like some military-style hats. Hats with perfectly flat brims - like boater hats - tend to accentuate the angles of a square face. Head wear with tall crowns can also make the face appear boxier or elongate a strong jawline.

What are the Best Hats to Wear with Suits & Tuxedos?

When pairing hats with suits and tuxedos, the goal is to enhance the overall look with sophistication, style, and appropriateness for the occasion.

Pay attention to color coordination by sticking to neutral tones like black, gray, navy, or beige for formal settings, while lighter colors work best for summer suits. Material selection also matters — choose high-quality materials like felt, wool, or straw based on the season and the fabric of your suit. Proportion is key, so balance the size of the hat with your suit proportions as well as your face.

Let’s consider four hats that go with suits and four with tuxedos, and share some suggestions for when to wear them. 

Hats to Wear with Suits

• Fedora – The fedora works beautifully with tailored suits. Felt fedoras in neutral tones elevate an otherwise day-to-day appropriate hat. Wear to business meetings, weddings, formal dinners, or stylish daytime events.
  

• Trilby – The trilby is slightly more modern and casual than the fedora and is great for semi-formal occasions. Its shorter brim gives a sleek, contemporary look, especially with slim-fit or modern suits. Wear to cocktail parties, smart-casual events, or daytime outings.

• Panama Hat – Ideal for lightweight summer suits made from linen, seersucker, or cotton. Choose a white or cream Panama with a black band for a fresh, elegant look. Wear to summer weddings, outdoor parties, or beachside formal events.

• Flat Cap – For a vintage yet stylish look, pair a flat cap with a three-piece suit or tweed blazer. Choose textured fabrics like herringbone or wool for colder seasons. Wear to smart-casual events, outdoor gatherings, or creative professional settings.

Man wearing a perfectly color-coordinated fedora hat with his suit

Hats to Wear with Tuxedos

• Top Hat – The epitome of elegance, a top hat is the go-to choice for tuxedos. Reserved for the most formal occasions and pairs exclusively with tailcoats or morning coats. Wear to white-tie events, galas, operas, or formal weddings.

• Homburg – An excellent alternative to the top hat. Adds a vintage, high-class look without appearing overly formal. Wear to black-tie weddings, gala dinners, or formal evening events.

• Fedora – For a more contemporary look, a fedora can pair beautifully with a tuxedo. Opt for high-quality felt in black to maintain the formality of the tuxedo. Wear to black-tie weddings, formal evening events, or high-end social gatherings.

• Boater Hat – A straw hat with a flat crown and brim, suitable for summer tuxedo events. Works best with white dinner jackets or light-colored tuxedos. Wear to summer galas, yacht parties, or destination weddings.

Can You Pair a Baseball Cap With a Suit?

The appropriateness of wearing a baseball cap with a suit depends on the occasion, the style of the suit, and the type of baseball cap. Mixing a baseball cap with a suit leans heavily into the modern, casual, or streetwear-inspired aesthetic, so it's definitely not appropriate for formal or traditional events. 

Ultimately, the key to choosing the right hat for your face, outfit and occasion is confidence. Experiment with different hats and brim angles – if you feel poised and polished in your statement piece, you likely look the part too! 

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