10 Tips for Wearing Hats

May 03, 2022 5 min read

Men's Tips for Wearing Hats

Are you looking for ways to wear and style your hats but aren't quite sure where to start? We've got you covered! In this handy hat guide for men, we'll provide 10 helpful tips for wearing different styles of hats. Read on to learn how you can match your hat to a specific setting, face shape, outfit, complexion and more.

1. Consider the Setting

When adding hats to your wardrobe, think of specific settings you can wear them in. For a more casual event such as a sports game, you might consider a color-coordinated baseball cap or snapback hat. A trip to the beach may call for a bucket hat. Meanwhile, a black or brown bowler hat might be suitable for a more formal setting or evening out. Carefully consider the environment and occasion before choosing a hat to wear.

2. Dress for the Season

Keep in mind that certain styles and materials of hats tend to suit different seasons. You'll want to wear a hat appropriate for the weather and time of the year. For fall and winter, consider wearing a beanie or toboggan that covers your ears to stay warm and stylish. For spring or summer, more lightweight hats, such as straw hats, visors, bucket hats and baseball caps, are ideal for warmer temperatures.

3. Flatter Your Face Shape

Hats come in many different shapes, materials and styles, and it's important to find one that fits your face's natural proportions. While it's a good idea to try on different types of hats to see which ones most flatter your face shape, here are some general styling recommendations that may help you out:

  • Oval face shape: This tends to be the most versatile face shape that allows you to wear a variety of hat styles, from snug beanies to wide-brim hats. Try on some different hats and choose one that harmonizes with your outfit and the occasion.
  • Round face shape: Fedoras, newsboy hats and baseball caps tend to flatter round face shapes, as they offer a more angular look.
  • Heart face shape: For a heart-shaped face, a beanie, beret, boater or medium-brimmed fedora can pair nicely with the width of your forehead.
  • Oblong face shape: Consider wearing a hat with a low crown and flared brim such as a fedora or sun hat. A large brim can help offset a longer face length.
  • Square face shape: Try wearing a hat with a round brim to soften the edges of your face. A cowboy hat, homburg or sun hat tends to work well with a square face shape.

4. Match Your Skin Tone

Similar to choosing clothes for your skin tone, try matching your hat to your complexion as well. For light and pale skin tones, darker hats in charcoal, brown and navy blue add a nice contrast. If you'd prefer a more lively color to balance your lighter skin tone, you might consider a rich burgundy or dark green hat.

For warmer complexions and olive skin tones, choose a hat color that's either slightly darker or brighter than the middle ground. A lighter gray, mustard brown or olive green tends to complement warm skin tones.

If you have a darker skin tone, you may want to avoid hat colors such as black, dark brown or navy that could clash with your complexion. Try out some contrasting shades such as khaki, red, gray or light blue.

Keep Your Hat Simple

5. Keep It Simple

When deciding how to wear a hat, keep your variety simple. Try not to mix patterns, go overboard with accessories or add excessive amounts of color to your outfit. For a more understated fit, a more elaborate or brightly colored hat tends to be more acceptable. If your outfit is already extravagant with lively patterns or colors, you'll likely want to opt for a more modest hat in a neutral color.

6. Coordinate Your Outfit

Try to choose a hat that coordinates with your outfit. Here are some hat and outfit styling tips to consider:

  • Straw or felt hats: These pair nicely with a variety of outfits, from khakis and a dress shirt to a simple T-shirt and jeans.
  • Beanies: Beanies complement a variety of fall and winter outfits like lightweight jackets, turtlenecks and sweaters. A pair of dark jeans, combat boots or retro sneakers pair nicely with this look as well.
  • Cowboy hats: These hats pair nicely with flannels, button-up shirts, blue jeans and cowboy boots.
  • Fedoras: Pair a classy fedora with a collared polo or Guayabera and some tailored trousers. For a more casual look, this hat also pairs nicely with a T-shirt, jeans and sneakers.

7. Factor in Other Accessories

Before selecting a hat for your outfit, consider if you'll be wearing any other accessories such as a scarf, belt or jewelry. If you already have ample accessories, you may want to reconsider adding a hat or replace one of these accessories with your hat to avoid a chaotic look. Carefully plan your outfit to ensure an even balance of accessories.

8. Pick Colors Strategically

When choosing a hat and outfit to wear, select and match colors strategically to organize your look. Here are some color matching tips to consider:

  • To add a splash of color to a neutral outfit, choose a bright, solid-colored or multicolored hat.
  • Coordinate your hat with your shirt and shoes by selecting a nice contrasting color.
  • Match your hat color to a scarf or other accessories in your outfit.
  • For a more formal outfit, match your hat to the color of your suit jacket and pants, then select a contrasting tie and undershirt color to balance your look.

9. Prioritize Comfort

Comfort is a key element to consider when selecting hats. Try on some different hats to see which materials, shapes and styles fit most comfortably. Maybe you've found that softer wool and knit hats are more comfortable than sturdy straw or plastic. On the other hand, cashmere or certain wools can feel itchy against your skin. Prioritize your comfort when choosing hats and select your preferred materials.

10. Be Confident

Finally, it's important to feel confident and stylish in any hat you're wearing. If you don't normally wear hats or assume they won't look good on you, think again! You can easily find the perfect hat to define your unique features and style while feeling confident in your decision. Don't be afraid to step out of your comfort zone and try some new hat styles — you may find it's the best decision you've made.

Shop Men's Hats at Penner's

Browse Men's Hats Online at Penner's

Looking for some new hats to add to your wardrobe? At Penner's, we offer an extensive and stylish selection to choose from. Whether you're on the hunt for a classy cap, a trendy felt hat or another style, you'll certainly find something to define your unique taste. Browse our men's hat selection today, or give us a call at 210-226-2487 and let us help you find the right piece!