Finding the Right Hats For Your Face – At Any Age!

In this guide, I’m going to pull from my 20-plus years as an image consultant to give you some valuable fashion tips that’ll help you pick the right hat for you – at any age. My recommendations are based on your face shape, unique qualities (personal brand), and color preferences!
You know those days…
When your outfit seems to be firing on all cylinders, but there just seems to be a piece missing…
Maybe it’s a hat? 
So you try on a couple…then a couple more. But nothing seems to fit that “look” you want.
We’ve all been there, but this DOESN’T mean that “hats aren’t for you.”
Many women steer clear of hats because they aren’t sure what kind is right for them. But, by understanding just a few fundamentals, you’ll be able to wear hats that make a statement and add a new dimension to your look.
By the end of this guide, you’ll know precisely the type of hat that not only fits your face shape but that will also bring you a sea of compliments!
Here’s what we’ll cover: 
  • Why Should Hats Be An Addition To Your Wardrobe? 
  • What Are Great Hats For Women Over 40? 
  • WHAT’S YOUR FACE SHAPE?!: How To Determine The Right Hat For You
  • 4 Things To Remember When Choosing Your Hat For The Day
  • Your Personal Style Coach For All Your Professional & Casual Looks

Why Should Hats Be An Addition To Your Wardrobe? 

As an image consultant, I’ve spoken with countless women who come to me looking for a style overhaul (female business owners and many other professional women). But this “overhaul” isn’t just for a single speaking event or business meeting—no, it’s an entire image overhaul for their personal brand…
Something that expresses their personality, professional interests, color preferences, uniqueness, and even individuality
It’s easy to think expressing individuality is only for the “younger crowd,” but that’s simply not the case when it comes to styling yourself for your prominent role or just everyday look. 
Hat’s are a great statement piece that shows all the attributes mentioned above. Women throughout history have worn hats to express who they were, their status, culture, mood, and even wealth.
So the big picture?
Hats show who you are to the world and help people subconsciously associate a physical piece (your hat) to your personality. Evidently, helping you get remembered more. (especially for those occasions where you’re networking and connecting with big names!)

What Are Great Hats For Women Over 40? 

In this section, I’m going to list some hats that you should be familiar with. The truth is, women over 40 who understand how to work with these hats can really take their personal and professional looks to new heights. 
And as your image consultant, it’s my duty to give you the inside scoop! 
But before I dive into mentioning different hats to think about, let’s first talk about important hat categories. 
Here are some hat categories and the specific hats that fall into them: 

  • Trendy Hats – Berets, Headband, Bucket, and Newsboy Hats
  • Classic Hats – Pillbox, Cloche, and Bucket hats 
  • Fun Hats – Cowboy, Cartwheel hats, and Beanies 
  • Elegant Hats – Bumper, Pillbox, and Bucket hats
  • Sporty & Relaxed Hats – Peach Basket, Newsboy, and Berets
  • Feminine Hats – Headband, Cloche, and Pillbox hats
  • Dramatic Hats – Fedora and Berets
  • Exotic Hats – Turban, Cowboy and Fedoras

As you can see, some hats fall into multiple categories, which makes them versatile. 
With that said, let’s discuss some “standouts” you might want to get your hands on when shopping online or at a mall – even without your image consultant in tow.

Sailor Hats

Sailor hats look good on most women—but especially women of smaller stature.  
They’re generally worn in the sunny spring and summer months, but you can find this style in leather, velvet, wool, knits, and other materials, which means you can carry this look into the colder months and cooler climates. 
That’s rights. Sailor hats might join you during the holidays!


Most online fashion stylists would tell you that headbands are currently in vogue. 
Trust me: they’re EVERYWHERE…
But with that said, personally, for me, they often give me a headache.  LOL.
But for other women over 40, headbands can offer a fun and youthful look and is versatile with so many complexions. Headbands come in tons of different styles and fabrics, so you’ll never run out of ideas and things to pair them with.  
Remember that headbands are more for casual looks than professional pieces (like Success thru Style avatar “Darla”). Therefore, if you’re looking for more sophistication, headbands aren’t the best choice.
If you own a headband or consider buying one, always feel free to post your feedback for our wonderful community at the bottom of this article!

Bucket Hats

Bucket hats are another favorite—as an image consultant, I’ve seen them pulled off quite well. 
They look best on women with smaller heads and frames but still good enough to look sleek on anyone. Bucket hats have stood the test of time and are considered a “classic” to this day. Just like the headband, it’s great for a casual outfit and things like enjoying the weekend with friends and family. 
If you’re ever unsure of your bucket hat look, feel free to snap a picture and send it to me, I’d be glad to take a look!

Cartwheel Hat 

Cartwheel hats have an elegant touch to them and look fantastic on larger scale women.
They have a wide brim that commands attention and fills the room with your air of confidence. They come in countless colors and materials and are the popular go-to for formal events.
On the other hand, if you’re petite or more on the slender side and you want a wide-brimmed hat, be sure to go with a light color like light blue, yellow, light brown, depending on your color palette.
Here’s a key thing to always remember: 
One of the biggest ingredients to successfully wearing a hat is confidence. So yes, make sure your hat is on brand, has the right color to it, and is in harmony with your skin, hair, and eyes: 
But confidence is the biggest equalizer. 
When you believe you look great, so will the rest of the room (some quick psychology for ya!).

Cowboy Hat 

Yup, good ole’ cowboy hats. A cowboy hat is a casual, sporty, and sometimes trendy look. 
It’s also very practical. 
What do I mean?
Well, it’s great for keeping the sun out of your eyes, and it’s durable enough to last you years. This makes cowboy hats a pretty good investment. Sure, it’s not the first thing you think of when you think of a “typical feminine or elegant look,” but it can be VERY flattering when worn with the right outfit!

Pillbox Hat

Pillbox hats are best for women with narrow foreheads. (As a result, they work especially well for diamond-shaped faces.) 
Pillbox hats are on the smaller side and come in casual looks and more sophisticated ones too! Like all hats, it’s all about pinpointing the right color for your personality and your lifestyle — and matching your face shape is the icing on the cake. 
And speaking of face shape…
Let’s go over the right hats that fit the shape of your face and create the stunning looks you’re going for. It really helps to have an understanding of face shape.

WHAT’S YOUR FACE SHAPE?! How To Determine The Right Hat For You 

Time for a dash of truth: 
Not ALL hats look good on ALL women. The biggest factor to take into consideration is the shape of your face.
Here are some valuable fashion tips that’ll help you pick the right hat for you – at any age. As an image consultant, it took me years to learn about face shape, personality, and color! But I’m offering you the valuable fashion tips I learned, that’ll help you pick the right hat for you – at any age. Learn about face shape, personality, and color!



If you have a circle-shaped face, your goal is to create length. So look for hats with tall crowns because they will give you that height you need. 
Here are some ideas: 

  • Medium to long-brim fedoras 
  • Pork pie hats
  • Trilby hats

Avoid anything low to the head and rounded—this will only accentuate the roundness of your face (which you don’t want!)



If you have an oblong-shaped face, you’ll want something with a little width and a shorter crown that will balance out the length of your face. A medium-sized floppy, cloche, or bucket style would work best if you fall in this category!



I have a square-shaped face and like to soften the angles–as do many of my style clients. In this case, I look for hats with a curved silhouette. Consider wearing floppies, cloches, or bowler-style hats to round out your features.



If you have a heart-shaped face, you may want to slim the forehead to make it appear narrower. Any hat with a brim that is medium in length will achieve this.



If you have an oval-shaped face, consider yourself lucky because most hats will look good on you.

4 Things To Remember When Choosing Your Hat For The Day

Be confident enough to have some fun with your choice of hats!

1. Step Outside Your Comfort Zone 

Sometimes, the hats that will look best on you will be “outside” your comfort zone. What I mean by this is that it’ll be a piece you wouldn’t typically wear, or maybe people aren’t used to seeing you in. 
Instead of shying away from wearing it, think of it as an opportunity to expand your “fashion comfort zone” and confidence–adopt a newer version of yourself. For example, maybe you’re going to a work event, and you’ve recently been promoted to a new position. This would be the perfect opportunity for you to try something new! 

2. Your Hat And Your Face Are A Team!

Think of your hat and face as two things that work together for a good look!
For example: if your face is small, be careful not to overpower yourself with too wide of a brim. Instead, look for a hat that is short to medium-sized. 
Conversely, if your face is on the larger side, look for styles with more width. This will help your face look smaller in contrast. 
The same technique works with facial features. For example, if you want your nose to look smaller, a great way to do this is with an exaggerated brim that echoes the shape of your nose.
The right hat can bring good attention to your face, and your face can bring a good amount of attention to your hat. 
See how they work together?
So when you adopt wardrobe tips from this article, be sure to keep this cute little quote in mind: “Your hat and your face are a team.” ~ Cyndy Porter, Image Consultant

3. Match It With Your Personality 

Finally, always, always, consider your personality
If you have an elegant/sophisticated personality, don’t just toss on a baseball cap or cowboy hat because it won’t match who you are, and you may not be as confident in it.
Try on a floppy hat, pillbox, or fascinator. 
If you’re the creative, whimsical, or bohemian type, you should look for hats with great colors, with a hint of eclecticism and embellishments in a style that tells your unique story

4. Color Matters!

Just like the clothes and accessories you wear, any hat you choose MUST compliment your natural color palette. If you are best in warm colors, your hat should be in warm tones as well. If you know your “wow” colors, wearing a hat in one of these colors WILL get you noticed…trust me!
Hats are a lot of fun and can go a long way to take your look to the next level. So always wear them with confidence.

Your Image Consultant in Northern Virginia

A Personal Style Coach For All Your Professional & Casual Looks!

Style doesn’t have to be difficult when you know what to look for. When it comes to hats, pinpointing your face shape and picking hats that accentuate your features, match your ideal colors, and express who you are, goes a long way. 
For years, as an image consultant and personal branding coach, I’ve helped women adopt the right wardrobe for themselves, and I would like to do the exact same for you. But there’s more! Learn how we work from the inside out to dress you from your distinct personal brand!
What are your thoughts? Feel free to comment below!
Ready to take your wardrobe to the next level? 
Schedule a Discovery Call with me today, and we’ll go over the things you need to know to look your absolute best year-round!



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