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How To Wear a Hat

Many people are convinced that they don't look good in hats. We get it - especially if you've never really worn a hat before, and it feels like you're entering a brave new world.

However, the correct hat can actually enhance your appearance by balancing out your face shape and frame, whether you've got a full head of hair or not. Consider this page the bible of how to wear a hat. Here we have guidelines on the best way to wear a hat in order to look your best.

Wearing the Right Hat for Your Figure

Your facial structure and overall shape are important factors to consider when selecting a hat. If you have a small face, you should choose a smaller hat. Conversely, if you have a large face, you should choose a larger, more dramatic hat. It's all about proportion.

No matter what your size or features, a hat should be no wider than the width of your shoulders. Here are a few more tips. If you are:

Adjusting a hat:

If a hat isn't flattering when you first try it on, you may need to adjust how it is placed on your head. If your face isn’t perfectly symmetrical in appearance (most of ours aren’t), chances are the hat will look better at an angle.  Try tilting the hat slightly to the right or to the left. Angle it from every direction and view it from every angle. Experiment until you find the optimal look. Here are some additional tips:

  • Glasses

    If you have glasses, try upturning the brim of your hat for a more flattering look. 

  • Hair

    If you have hair, try tucking your hair behind your ear or putting your hair up for the best look, and so that your features can fully be on display.

  • Earrings

    Experiment with different earrings to spice things up. For women with hair loss, large statement earrings can help balance your look and focus attention back to your face.

  • Get Crafty

    Adornments from your local craft store can be used to personalize your hat. Flowers, ribbons, beads and more — the possibilities are endless.

  • Hairpieces

    For women with hair loss, we offer Velcro bangs and a wide variety of hairpieces with open tops that can be worn underneath your hat. They add the appearance of hair without the heaviness of a full wig. 

  • Hat Liners

    If you find hats scratchy due to hair loss, try wearing hat liners underneath the hat to add a layer of protection between your scalp and the hat. Hat liners also allow you to wash your hat less frequently.

Picking out hats can be overwhelming, especially on a tight budget. You might think you have to break the bank, buying enough hats to match all your outfits. Luckily, this is not the case. With the help of accessories, you can turn one hat into hundreds. There are several things you should consider when choosing a hat to accessorize.

  • Style

    Choose a hat that is simple and casual to maximize accessorizing options.

  • Color

    Try to select a hat in a neutral color, or a color that matches many of your outfits. You can add a punch of color with various accessories.

  • Comfort

    Choose a soft and breathable fabric suitable for daily use. We like hats made of bamboo and cotton. Bonus? These materials are easy to wash. 

Top picks for choosing hats to accessorize: We recommend our Cozy Caps, Three Seam Turbans, and Denim Bucket Hat for starters. These are basic neutrals that can achieve many different looks. Oh, and they’re super-duper comfortable, day after day. 

Types of Hat Accessories

When it comes to accessorizing, the possibilities are endless! Here are some suggestions:

  • Headbands

    Placing an elastic headband around the brim of your hat can completely change its effect. For example, a beaded headband can turn your casual cozy cap into a chic statement piece.  A wide variety of headbands are available to suit every style, from hippy to Hepburn. Headbands can be purchased at many retailers, including Headcovers. If you're crafty, you can make your own.

  • Pendants, Flower Pins and Broaches

    Clipping a pendant orbroach to your hat can add heaps of visual appeal. Headcovers sells beautiful floral pins to decorate your hat. If you're festive, you can purchase or make pendants that suit the season, such as snowflakes or pumpkins.

  • Scarves

    Tie a head scarf at the base of the cap to add a pop of character. Our rectangular accessory scarf and mini scarf are ideal for achieving an array of eclectic looks. With three mini scarves, you can create a braid. With two mini scarves, you can create a twist. For more variety, tie the scarf into a bow or rosette. Our Rosette Scarf Twists are another favorite that dresses up a hat and also adds the appearance of volume.



Choosing the Right Hat for Your Face Shape

Selecting the optimal hat style for your face shape can help you look and feel your best. There are a few ways to determine your face shape:

Mirror Method: Stand in front of a mirror and pull your hair back. With a bar of soap or lipstick, trace the outline of your face onto the mirror. Compare the outlined shape on the mirror to the pictures below.

Tracing Method: Trace the outline of your face from a photograph. Observe to see what shape is revealed.

Measuring Method: With a ruler or measuring tape:
  1. Measure across the tops of your cheekbones.
  2. Measure across your jaw line from the widest point to the widest point.
  3. Measure across your forehead at the widest point.
  4. Measure from the tip of your hairline to the bottom of your chin.
  5. Compare measurements to the guide below.

face shape and hats



Oval Shaped Face

Description: When you measure your face, your length is equal to about one and a half times the width. Your face is only slightly narrower at the jaw line than at the temples, with a gently rounded hairline.

Best Choices: Because of your face is balanced and in even proportion, you can wear almost any style.

Avoid: The crown of the hat should never be narrower than your cheekbones. Hats should be no wider than the width of your shoulders.



Round Shaped Face

Description: Your face is approximately twice as wide as it is long. You have a round chin and a round hairline. The widest point is at the cheeks and ears.

Best Choices: Styles that add fullness and height at the crown. Select hats with sharp lines, tall crowns, high brims and asymmetrical shapes. Straight brims should be slanted to create flattering angles. Wear your brims on an angle whenever possible. The crown of the hat should be at least as wide as your face. A hat with a higher brim will help lengthen your face.

Avoid: Rounded crowns, circular or floppy-shaped hats.



Heart Shaped Face

Description: When you measure your face, it is narrow at the jaw line and wide at the cheekbones and/or forehead. Your face appears wide at the temples and hairline and narrows to a small, delicate chin.

Best Choices: Medium brimmed hats are ideal because they do not accentuate a wider forehead or a narrow chin. Heart shaped faces look good in almost any hat style. Hats with asymetrical brims are a good choice. When you have a wide forehead and a narrow chin, the brim of a hat can help balance a wider forehead. If you go too wide, your chin will appear even more narrow.

Avoid: Avoid hats with brims that are small because they will make your forehead look bigger. Avoid wide brimmed hats or hats that are too full as these will make your chin look more narrow.



Square Shaped Face

Description: Your face is about as wide as it is long. You have a strong, square jawline and a square hairline.

Best Choices: Wear your brims on an angle whenever possible. Wide brimmed hats with a rounded crown can help soften a wider square jawline. Choose hats that sit high on your forehead to elongate the bottom half of your face. Feminine hats with curvy lines will help soften the lines of your face. Round and asymmetrical hats will contrast a sharp jawline.

Avoid: Hats with a flat top or a tapered crown.



Diamond Shaped Face

Description: Your face is the widest at the cheekbones, with a narrow forehead. Your forehead and jaw line are approximately equal in width. Your shape is a cross between a heart and an oval.

Best Choices: Almost everything works with your balanced face shape. Try a variety of styles.

Avoid: You can wear almost anything.



Oblong or Rectangular Face Shape

DescriptionYour face is longer than it is wide. It is about the same width at the forehead and just below the cheekbones. Individuals with oblong shapes may have a very narrow chin or a very high forehead. Your face appears long and slender.

Best Choices: Choose wide hats with short crowns. Hats with wide flat brims or curled/floppy brims work well. Try pulling the brim of your hat down to your eyebrows to shorten your face.

Avoid: Narrow brims and hats with high crowns, which will make your face look even longer.



Pear Shaped Face Shape

DescriptionYour face is characterized by a narrow forehead and is widest at the jaw, with a round chin.

Best Choices: The best styles will create width at your forehead and temples, giving the illusion of an oval face. They will draw attention to the upper part of your face. Choose hats with a full (but not tapered) crown and a wide brim.

Avoid: Hats with tapered crowns, which tend to accentuate a wide jaw.


  • Find inspiration

    Browse Pinterest, Instagram and fashion magazines like InStyle and Glamour to see how the style stars make it work.

      Celebrities pay big money for professional stylists to tell them how to wear hats. Find an outfit or two that speaks to you and try to replicate it with items from your own closet.
  • Match Aesthetics

    A velvet turban may look out of place with casual shorts and a t-shirt, just as a sun hat won’t look good with a cocktail dress (unless you’re at the derby). Matching aesthetics can help your hat look more natural with your outfit.

      Pair the velvet turban with your date night dress, and a sun hat with your favorite summer separates.
  • Mix Colors & Textures

    A red hat with a red hat will certainly draw attention, but that may not be the vibe you’re going for. Instead of matching colors exactly, try matching the underlying tones – cool with cool, and warm with warm. (For example, a warm cream-colored hat with a red dress would look fabulous, just as a blue blouse and cool grey fedora complement each other nicely).

Try to avoid matching distinctive fabrics. A denim hat and denim shirt may overload the senses, but a denim hat with a plaid cotton or fleece shirt is positively dashing. Variety in texture is pleasing to the eye and can help add a certain je ne sais quois to your overall look.

How to Wear a Hat with Long Hair

Long hair looks fabulous topped by hats. Here are three of our favorite ways to style your long hair beneath a hat:

  • 1

    Parted in the middle and straight

    If you’re wearing a sun hat or wide-brimmed hat. Straight hair balances out the drama of a wider brim.

  • 2

    Wavy and textured.

    If you’re wearing a fedora, bucket hat or newsboy cap. Added volume enhances the attitude of these types of caps.    

  • 3

    3. Parted to the side and tucked behind one ear

    If you’re wearing a cloche or baseball cap. Hair that’s parted and tucked behind one ear enhances the femininity of a cloche and adds a touch of class to a baseball cap. 

How to Wear a Hat with Short Hair

Short hair and hats can be smashing companions, but it may take a bit of experimenting to land the perfect look. Here are our top three tips for how to wear a hat with short hair:

  • 1

    Let your hair hang out.

    Whether you’ve got dramatic bangs or an asymmetrical cut, let the length that you have peak out from beneath your hat to add visual interest and soft the overall appearance.

  • 2

    Accessorize with a hat band or scarf.

    Wrapping a scarf or hat band around the crown of your hat can add a touch of femininity and texture to your outfit, balancing out the stark jut of a brim.

  • 3

    Add some earrings.

    A fedora, dangly earrings and a pixie cut – is there anything cooler? Hats and short hair practically beg to be complimented by some beautiful jewelry that can help enhance your overall look.

Is a hat supposed to cover your ears?

It depends on the hat. Knit caps, like beanies and winter hat styles, can come down to cover your ears if it feels comfortable and protects you from the elements. But hat styles like fedoras and sun hats — anything with a brim, really — should not cover your ears. 

Structured hats should sit about ⅛” to ½” above your ears, depending on your personal preference and comfort level.

If you’ve fallen in love with a hat that covers your ears because it’s too big, consider lining the inner rim with a hat sizer, an adhesive tape that will provide a more secure fit. 

Can I wear hats with heels?

Absolutely! Hats with heels are a stylish statement that works well with streetwear as well as for fancier occasions like evening cocktails or Easter Sunday. Look at celebrities like Blake Lively and Jennifer Aniston for heel and hat inspiration — those ladies frequently rock the look. 

Can I wear fedora hats inside?

Sometimes, yes. It depends on where you are, who you’re with and what the occasion is. Generally, fedoras are associated with outdoors because the brim is meant to be functional, protecting you from the elements. But if you wear a fedora to a casual party or get-together, and it’s clearly part of your outfit, then it’s OK to keep it on. In contrast, fedoras might not be as appropriate at a sit-down dinner or professional event (unless you work in the entertainment industry or the arts, in which case you can probably pull it off). 

We know hat etiquette may pose frustrating, especially if you’re dealing with hair loss. Our primary rule of thumb is always to do what’s comfortable. If you have a formal event to attend and would feel self-conscious in your tried-and-true fedora, no sweat! Try an elegant turban or slip-on headscarf. You’ll feel confident and look great so that you can focus on living in the moment. 

I’ve lost all my hair, and wearing a hat looks weird. What should I do?

If you’re wearing a hat to help conceal hair loss but feel uncomfortable with the appearance of your bare skin beneath it, we totally understand. While you have nothing to be embarrassed by, figuring out what feels good to you may take some trial and error. Here’s a few ideas: 

Halo hair. Halo hairpieces are literally bands with hair attached that you wear around the circumference of your head. A lightweight, inexpensive alternative to full wigs, halo hair can be mixed and matched beneath your favorite hat. 

Attachable bangs. Perhaps adding some forehead fringe is all it’ll take to make you feel more comfortable. Our Cardani Human Hair Bangs and Ultimate Fringe bangs can be attached via Velcro to the inside rim of any hat, turban or pre-tied scarf that you please.  

Ponytail headband. Wear a ponytail headband with your favorite baseball cap for the appearance of hair without the hassle. Our customers love it for how easy it is to wear, and how natural it looks. 

Padded headband. If you’re not sold on the idea of replacement hair, a padded headband might be what you’re looking for. Wear it beneath hats and scarves to achieve a fuller look and more balanced proportions. 

Pre-tied scarf. If all else fails and you still feel uncomfortable in your hat, try switching gears completely with a pre-tied scarf. These are just as convenient as hats — slip ‘em on and go — but can look a little less stark than wearing a hat if you’re dealing with total hair loss. The Easy On Pre Tied Headscarf and Bailey Newsboy Head Wrap Scarf both have fullness built right into the head covering. 

Should I wear my hat slightly tilted or straight on?

It’s up to you. With hats, anything goes, as long as it matches your attitude and personal style – though many people do find that hats look better slightly askew.

Pro tip: put on your favorite outfit and stand in front of the mirror, playing around with different angles for your hat placement. Maybe even send pictures to friends and ask which way looks best. Once you feel confident in how you’ve positioned your hat — whether it’s positioned straight-on or cocked slightly to the side — just roll with it. Everyone else will, too.


For more helpful tips and shopping, visit the following pages:

Women's Hats

Cancer Hat Buying Guide

Head Scarf Buying Guide


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Comments, Questions & Ratings

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Such good info Review by How To Wear a Hat
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I have spent most of my life feeling super self conscious and afraid of wearing hats because I thought I looked like an idiot! Now after using this info and using the tracing method to determine I have a round face, I have been able to choose the perfect hats! I now wear hats all the time. Literally ALL the time! Thank you so much!! (Posted on 04/29/2019)

Mrs. Review by How To Wear a Hat
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I love this resource! I would love to see face shape recommendations on product pages. I'm still not sure I know how to buy a turban with my face shape (round...I think). It would make it so easy to see what face shapes go with your hat selections. Just a thought. Thanks! (Posted on 12/08/2018)

Pat Review by How To Wear a Hat
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I have been avoiding buying hats because I have a small head. After viewing this site I know now what to like for when buying a hat. Thanks for this valuable and helpful information. (Posted on 11/03/2016)

M. Review by How To Wear a Hat
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I really have found more hat choice info here than elsewhere. Thank you for the invaluable assistance. (Posted on 08/26/2016)

Great resource! Review by How To Wear a Hat
100 100

Thank you for the helpful tips on selecting the right hat. This is the best resource I have found and I feel better prepared now to choose something flattering for me. (Posted on 12/31/2014)