Hat Styling Tips: How To Wear Hats — The Wardrobe Consultant (2024)

Hats are a timeless accessory that can effortlessly elevate any outfit, but if you feel like you’re not a hat person, you might be hesitant to embrace the look. Whether you're a hat enthusiast that wants to expand your collection or a hat newbie looking for tips to start incorporating them into your wardrobe, I’ve got you covered.

This blog post will dive deep into a variety of popular women's hat styles. And I’ll also share some expert styling tips, advice on choosing the perfect hat for your outfit, and suggestions for overcoming any fears you may have about wearing hats (hello hat hair!!).

So, get ready to become a hat person with my top recommendations for mastering the art of hat-wearing.

Have fun and try on some hats

Most people don’t just put a hat on and look good right away. It often takes some trial and error. As well as some tweaking. Most people's faces are not perfectly symmetrical, so hats will look best when adjusted a bit - either tilted to the side, pushed down on the brow, or tilted back on the head - all depending on one's face shape and the style of hat.

Also wearing glasses, large earrings and having a lot of hair can additionally affect how the hat looks and is styled. I can’t cover every possible iteration here, but know these are elements to keep in mind.

The most important thing is to just have fun. Try on a BUNCH of hats and see what style and shape makes you feel great. When you know, you know! And you do not know if you don’t try.

Before we dive in, let’s chat about various hat styles. I’m focusing on the five most universally flattering styles - meaning the styles that work for most face shapes. That way you’ll know what you’re looking for when you start trying all the hats on.

If you’re a new hat wearer, it’s usually helpful to start at a store that has a variety of styles and colors to pick from. It will offer you the best chance of finding a hat you like.

A traditional hat store such as Goorin Bros or a department store like Nordstrom offers a wide selection of hats to pick from. There are many smaller hat stores in different cities and these shops have experienced sales people that can help you find the best hat for you.

Fedora

The fedora is a timeless and elegant hat style - and one that you probably think of when you think of wearing a hat. Fedoras can be easily incorporated into various outfits and worn on many occasions.

Its versatility and suitability for most face shapes make it a popular choice among women looking to add a touch of class and sophistication to their wardrobe.

The fedora is a classic hat with a medium-sized brim and a pinched crown. Typically made from materials like wool, felt, or straw, fedoras can be adorned with ribbons, bows, or feathers for added flair.

Who it works best for: Fedoras are suitable for most face shapes but are particularly flattering on oval, square, and heart-shaped faces.

Outfits: Pair a fedora with a tailored blazer, jeans, and ankle boots for a chic daytime look, or dress it up with a midi dress and heeled boots for a more sophisticated ensemble.

Floppy Sun Hat

The floppy sun hat is a fashionable and functional accessory for warm weather, providing both sun protection and a touch of sophistication. Suitable for most face shapes, this hat style can effortlessly elevate your summer wardrobe and keep you looking stylish and chic throughout the season.

The floppy sun hat is a summer essential with a wide brim that provides shade and protection from the sun. Often made of straw, canvas, or cotton, these hats come in various colors and patterns.

PRO TIP: If your sun hat loses structure over time, here is a quick tutorial on how to bring it back to life!

Who it works best for: Floppy sun hats are suitable for most face shapes and have a true element of functionality as well.

Outfits: Pair a floppy sun hat with a maxi dress and sandals for a beach-ready look, or wear it with a light, flowing blouse and tailored shorts for a stylish brunch outfit.

Baseball Caps

Incorporating a baseball cap into your wardrobe adds a relaxed and sporty touch to your everyday style. With endless design options and the ability to suit most face shapes, this hat style is a great choice for women looking to add a touch of casual flair to their ensembles.

The baseball cap is a casual, sporty hat with a rounded crown and a stiff, curved brim in the front. Often made from materials like cotton or polyester, baseball caps can feature team logos, brand names, or just be a solid color.

Who it works best for: Baseball caps are a universal style that suits most face shapes, making them an easy and versatile choice for any woman.

Outfits: Pair a baseball cap with a simple t-shirt, jeans, and sneakers for a laid-back, weekend look, or dress it up slightly by adding a blazer to the t-shirt and jeans, for a casual yet put-together outfit.

Bucket Hats

Bucket hats are a playful addition to your hat collection and can instantly inject a touch of casual, carefree style into your wardrobe. With their wide range of colors and patterns, bucket hats offer endless styling possibilities and can complement various face shapes, making them an excellent choice for women looking to experiment with different hat styles.

The bucket hat is a casual, unstructured hat with a wide, downward-sloping brim and a flat crown. Originally designed for fishermen, bucket hats are typically made from cotton, canvas, or denim and can feature various colors and patterns.

Who it works best for: Bucket hats work well for most face shapes, especially oval and round faces, as they help create balance and add a fun, laid-back vibe to any outfit.

Outfits: Wear a bucket hat with a relaxed, oversized shirt, high-waisted shorts, and sneakers for a youthful, street-style look, or pair it with a casual midi dress and sandals for a breezy, summer look.

Beanies

Beanies are a must-have accessory for colder weather, because they provide warmth and comfort while adding a touch of style to your outfit. With their versatility and wide range of options, beanies can be easily incorporated into your winter wardrobe and are suitable for most face shapes, ensuring that you stay fashionable even when temperatures drop.

The beanie is a cozy, knit hat that fits snugly on the head and can be worn pulled down or with the edge folded up. Made from materials like wool, acrylic, or cotton, beanies are perfect for keeping warm during colder months and come in various colors, patterns, and styles.

Who it works best for: Beanies are a versatile hat style that suits most face shapes, making them an ideal choice for almost anyone looking to stay warm and stylish during the colder months.

Outfits: Pair a beanie with a chunky knit sweater, jeans, and ankle boots for a cozy, autumn-inspired look, or wear it with a long coat, scarf, and leggings for a chic, winter ensemble.

Select a hat that complements your face shape. For example, if you have a round face, opt for a hat with a higher crown and a medium-sized brim, like a fedora. If you have a long face, a hat with a wider brim, such as a floppy sun hat, can create balance.

This is a very similar concept to dressing for your body shape. At the end of the day, the goal is to create visual balance and proportion where it may not naturally occur (which is most people btw). So keeping that in mind is important. If your face is rounder, add angles with your hat. If your face is longer than it is wide, add width with your hat.

Not sure what your face shape is? Here’s how to find out:

1. Measure your face length, forehead width, cheeks width, and jawline length.

2. Input the measurements into this Face Shape Calculator.

Oval/Diamond Face Shape

Best Hat Styles: Your face is balanced and quite proportional, Lucky you! You can wear almost any style.

What to Avoid: Medium brimmed hats are best. Make sure the crown of the hat is NOT narrower than your cheekbones. Hats should be no wider than the width of your shoulders. This will help create balance and proportion overall.

Rectangle/Oblong Face Shape

Best Hat Styles: Opt for wide hats with short crowns. Hats with wide flat brims (sometimes called a boater) or curled/floppy brims (like a sun hat) work well too. Pulling the brim of your hat down to your eyebrows can help shorten your facial proportions.

What to Avoid: Narrow brims and hats with high crowns are not your friend. They will accentuate the length of your features and make your face look even longer. (This is my face shape, if you watch my video you’ll see that these styles are the ones I have a thumbs down to)

Pear/Triangle Face Shape

Best Hat Styles: The hats for you create width at your forehead and temples, creating the illusion of an oval face. The goal is to draw attention to the upper part of your face. Choose hats with a full crown and a wide brim.

What to Avoid: A hat with a tapered crown will accentuate the width of your jawline as opposed to balance it.

Round Face Shape

Best Hat Styles: Opt for hats with sharp lines, tall crowns, and high brims, such as a fedora. Wearing your brims on an angle helps create angular balance to your rounder facial features. A hat with a higher brim will help lengthen your face.

What to Avoid: Shy away from rounded crowns, and floppy-shaped hats. Think of this as the rule of juxtaposition, but for hats/faces. If your face is round, ideally you want a hat that is more angular, so they complement one another.

Square Face Shape

Best Hat Styles: Wide brimmed hats with a rounded crown help soften a square jawline. Also, hats that sit high on your forehead can help elongate the bottom half of your face. Feminine hats with curved lines as well as round or asymmetrical hats will help soften the lines of your face. Tilting the brim of your hat is key for a square face as it visually creates a narrower look.

What to Avoid: Hats with a flat top or a tapered crown will mimic the square nature of your face and accentuate it, as opposed to complimenting it with the contrasting features.

Heart Face Shape

Best Hat Styles: Heart shaped faces look good in almost any hat style.The brim size is what will make or break the look. When you have a wide forehead and a narrow chin, the brim size of the hat becomes very important as it will be what creates harmony or imbalance with the hat.

What to Avoid: Small brimmed hats will make your forehead look disproportionately large. And conversely, wide brimmed hats will make your chin look extra small.

Coordinate with your outfit

Your hat should complement your outfit, not compete with it. Make sure the colors, patterns, and materials of your hat work well with your clothing. If your outfit is busy or features bold patterns, opt for a simpler, more neutral hat.

Mind your hairstyle

When wearing a hat, consider how it will affect your hair. Adjustable hats, like baseball hats, can accommodate a variety of hairstyles, while more structured hats, like fedoras, may require more careful styling. Although personally, I love how wearing any hat provides respite when I’m having a bad hair day.

Be confident

Confidence is key when wearing a hat. Embrace your style and wear it with pride. Remember that a well-chosen hat adds a finishing touch to your look.

The potential of having hat hair after you take off your hat is one of the major things that prevent people from rocking a hat. While I can’t totally guarantee that you won’t experience this at least a little bit, I do have some tips to help you avoid it!

Choose the right hat size

Make sure your hat fits properly. A hat that is too tight can cause your hair to become compressed and flattened. Opt for a hat that is snug but not overly tight, allowing some room for your hair to breathe.

Minimize hair product usage

Overusing hair products like gels, mousses, or creams can make your hair more prone to hat hair, as they weigh your hair down and make it more susceptible to flattening. Use lighter products, like volumizing sprays or dry shampoos, to give your hair some lift without weighing it down.

Dry hair completely before wearing a hat

Putting on a hat when your hair is still damp can cause it to dry in a flattened shape. Make sure your hair is completely dry before wearing a hat to avoid this issue.

Opt for looser hairstyles

Tight hairstyles can make hat hair more noticeable. Instead, wear your hair in loose, natural waves or curls, or try a low bun or braid. This will help your hair maintain some shape and volume when you take off your hat.

Refresh your hair after removing the hat

When you take off your hat, use your fingers or a wide-tooth comb to gently shake out your hair and revive its natural shape. If needed, apply a small amount of dry shampoo or volumizing spray to the roots to add some extra lift.

With a great hat comes great responsibility. When it comes to hat etiquette, follow these general guidelines:

• Historically, etiquette called for removing your hat when indoors (unless it's part of your outfit or for religious reasons). However, that is not as common in recent years.

• In the US, hats are not typically worn at formal events like weddings or funerals. It is not a faux pas. It is just not as common as it is in other countries like the UK.

• Be mindful of your hat's size and brim, ensuring it doesn't obstruct others' views or invade their personal space.

Still Hesitant To Wear Hats?

If you’ve avoided hats your whole life, I know you might need a bit more convincing before you really consider adding them to your wardrobe. Here are some tips for dipping your toes into the world of hats:

Start with a versatile hat style: Choose a classic and versatile hat style which can be easily incorporated into various outfits and occasions. Baseball caps or beanies can be good starter hats. These styles are flattering on most face shapes and can help you ease into wearing hats with confidence.

Practice wearing hats at home: Before wearing a hat in public, practice wearing it at home to become comfortable with how it feels and looks on you. This will help you build confidence in your hat-wearing abilities and give you a chance to experiment with different hairstyles and outfit combinations.

Embracing the world of hats can open up a whole new realm of style possibilities for women over 40. From the classic elegance of fedora hats to the casual chic of baseball caps and bucket hats, there's a hat style to suit every taste and occasion. By understanding your face shape, experimenting with different hat styles, and coordinating them with your outfits, you can confidently incorporate hats into your wardrobe and enhance your personal style.

Don't be afraid to step out of your comfort zone and try something new. Remember, the key to pulling off any hat is confidence. As you explore these popular hat styles and learn how to style them to best suit you, you'll not only look fabulous but also feel empowered and self-assured. So, go ahead and give hats a chance – you might just discover your new favorite accessory.