If you’ve ever seen someone wearing a hat and really pulling it off, you’ve probably wondered what it’s like to know you’ve chosen the perfect headwear. Almost everyone has had a negative experience with trying on hats in a store, but that doesn’t mean you shouldn’t be a hat person. In fact, there’s a style out there that’ll suit your facial shape and outfit. Whether you have many hats in your collection or just one, you should explore this ultimate guide to choosing the right hat for your outfit to ensure you look fabulous.

Consider Your Face Shape

Your face shape is arguably the most important factor to consider before choosing a hat. If you’re unsure about your unique face shape, take a few minutes to learn more about each one and decide which best aligns with yours.


  • Round: If your face has the same width and length measurement, you most likely align with the round shape. You may also have a rounded chin and full cheeks.
    • Fedoras and beanies are the best choices for round faces.
  • Heart-Shaped: Those with heart-shaped faces have broader cheeks and foreheads with a narrower chin. If you have wide cheekbones and a pointy chin, this is most likely your face shape.
    • You can rock a fedora, ball cap, or sun hat.
  • Square: If the distance from your chin to your forehead is almost the same as the distance from cheek to cheek, you may have a square-shaped face.
    • Consider wide brims—cowboy hats, floppy options, and more.
  • Triangle: If you have a larger jawline, smaller cheekbones, and a narrow forehead, you most likely have a triangle or pear-shaped face.
    • Beanies look great on you!
  • Oblong: You may have an oblong-shaped face if your face is longer than it is wide. With that said, your cheekbones, jawline, and forehead are approximately the same width.
    • Choose wide brims—cowboy hats, structured or floppy wide-brimmed hats, and more.
  • Oval: If you have an oval-shaped face, your forehead will be a bit larger than your jawline, and you may have a rounded chin.
    • Almost every style looks great on you!

Now that you know more about your unique face shape, you can start learning more about styles that suit you. Your body type may also play a significant role in choosing the best hat style.

Match Your Physique or Body Type

Although your face shape is a significant consideration when choosing the best hat style, you must also consider your physique. With that said, those with a different build than you may be able to wear different styles with a completely different appearance.

You want your hat to balance your body, not cause disproportions. For instance, top hats and styles with upward-pointing brims—like cowboy hats—make you appear taller. On the other hand, down-turned and wide brims may make you appear shorter.

Pro Tip

Your hat shouldn’t be wider than your shoulders. Obviously, this width can differ from person to person—people with larger builds can opt for wider hats.

Think About Your Personal Style

Your sense of style is an incredibly important factor to consider before committing to a hat. Even though you truly like the style, you should ask yourself whether it fits into your aesthetic. If not, you probably won’t wear it on a regular basis with your usual outfits.

First of all, you should choose a color that fits your wardrobe. Typically, neutral colors are the best options when it comes to hats, as they go with practically any outfit. However, your refined style is a huge deciding factor.

Preppy Style

If you prefer the preppy style, you should consider structured brim hats, like top hats, boaters, and Bretons styles.

Boho Style

Your boho closet should include floppy wide-brimmed hats and wide-brimmed fedoras. If you enjoy boho styles but don’t love hats, be sure to try one of these, as it’ll look fabulous.

Vintage or Elegant Style

The vintage or elegant style is still relevant today, and hats are a significant part of the design. Choose fascinators, cloches, and pillbox styles for your wardrobe.

Lazy or Athleisure Style

If you tend to embrace the lazy or athleisure style, you should consider adding several ball caps to your collection. If you want something unique for your wardrobe, consider a women’s smiley face trucker hat to add flair and uniqueness to your otherwise leisure outfits.

Different Outfits in Different Seasons

Your hat choice should fit with the season, as some styles aren’t suitable for cold or warm weather. With that said, consider these different options for different seasons.


You’re more likely to wear warm clothing, coats, scarves, and more in the winter. The cold temperatures and winter weather conditions should convince you to keep your head and ears warm. In this case, a beanie is the best possible hat choice for the winter months.


Spring begins to warm up a bit, but it’s not quite time to hang out by the pool. This is the time for light colors; therefore, you should pair your light-colored t-shirt with a light shacket and a floppy, wide-brimmed hat.


Summer is the perfect time to spend time outside soaking up the sun. Consider a floppy straw hat with your swimsuit to protect your face and hair from harmful UV rays, and look fabulous doing it!


Fall is the perfect time to break out your sweaters, jeans, and boots, but wearing your favorite structured wide-brim hat is also a great idea.

Now that you have the ultimate guide to choosing the right hat for your outfit, you’re ready to find one that suits your personal style and your face shape. Although some hats look better on you than others, that doesn’t mean you can’t wear whatever you like. After all, you should embrace what you love and wear whatever makes you feel comfortable. Hats can enhance your outfit and create interesting dimensions in your overall appearance. Whether you choose a beanie or a floppy wide-brimmed hat this weekend, you’ll look absolutely fabulous!

Ultimate Guide To Choosing the Right Hat for Your Outfit

January 27, 2023 — Monica Spruiell