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Best Hat Styles for Women With Short Hair (updated)

by Tina Boomerina (Christina Gregoire)

As you may know, I am a bit of a hat freak. And, when all of you women over 40, 50, or 60 get to be a bit older, and your hair becomes a bit thinner, you’ll start to understand why I love hats so much. Hey, my hair has been baby fine and very thin for my entire life, so I’m really into chapeau chic.

read about hat styles for short hair

Cute Hats Short Hair

And, this is the right place to ask your hat questions.

What Kinds of Hats Are Good for Short Hair?

Here is a message I got the other day:


Love your website and Pinterest boards. I would love to wear hats. Would you kindly talk about different styles and shapes and what to do with short hair and what jewelry I can wear and help!

Thanks, Suzanne

Dear Suzanne,

I have short hair and I love hats.

Personally, I don't think it matters if your hair is long or short. What matters is that your hat looks proportional to your body type, looks good with your face shape, and looks right with your outfit.

Your Hat Should Go With Your Outfit

It’s more important for your hat to go with your outfit than to go with your hair.

read about cute hats

Cloche Hats for Short Hair


When I’m getting dressed, I usually start at the top and work my way down (in my mind) as I'm planning what to wear. I start with one of my hats and then I look for clothing that goes with my chosen chapeau. Yes, I have THAT many hats. Well, my husband says I have 100 hats, but many of them are cheap little $2 toques from my travels. Those don't really count, do they?

However, you (Suzanne and other readers) will probably be getting dressed first and then deciding whether or not you want to add one of your hats to your ensemble.

(Ensemble = a fancy word for a pair of  jeans and a T-shirt or whatever you’re throwing on for the day). And, that reminds me of a very important point:

  • Your hat (color) does not need to match the color of your outfit.


read hat tips for women

Your Hat Need Not Match

Your hat doesn't need to match the color of your outfit, it just needs to have the same “feel” as the rest of your outfit... (unless you are going for an edgy look and you want to wear a "dressy" dress with a pork pie)... but that’s for Hat Style Class 102. And in general, you don’t really want to be too “matchy” or you’ll end up looking like QE2.

Not that the Queen looks bad… I just want you to look like you’re having a bit more fun... I want you to shake things up and make it lively.

Small Brims and Short Hair

I don’t think your hair length really matters too much when choosing a hat. Sometimes, your hair becomes a factor, but hair length is usually more like an afterthought. Almost all hats look just fine with short hair.

The only exception might be big floppy hats. Big floppy boho hats usually look slightly better with longer tresses, because the long hair gives a type of balance to the large wavy brim. (Large floppies are a retro hippie look from the late 60s and early 70s.)

Other than that, I wear the same hats now (with short hair) that I wore when I had long hair. Whenever I felt that my long hair didn't "go" with my hat, I just pulled my skimpy locks up into a high ponytail and popped on my hat over everything.

read about the best styles for hats

Cloche Hats Different Shapes

And, when my hair was chin length or too short for a pony, I just pinned it up as best I could and the hat made me look fab by covering my crappy hair. (Use bobby pins with rhinestone flowers. The embellishment helps keep your hat on even though no one sees the fancy pins.)

Should Your Hair Peek Out So it Shows?

In general, you should have some of your short hair peeking out to soften your look… so pull your bangs (or some wispy tendrils) out from under your hat. Without that, your look could be too severe… but not always.

With some hat shapes, it is neither necessary nor desirable to have your hair showing. Too many websites are flat out wrong about this! Some flapper-style hats look JUST FINE without any hair peeping out.

Back to hair length, one thing that could matter with short hair is if you have a hairdo that would be flattened by wearing a hat. Of course, you don’t have to take your hat off unless it’s necessary for your job. (See article about hat etiquette at the end of this article.)

On the other hand, if you have short hair, it makes me think that you will look good in a hat with a smaller brim, such as a small fedora, a cloche, a beret, or an English Mod cap.

(Article Continues)

Keep reading about cute hats for women with short hair on page 2.

Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

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  1. Suzanne

    Ooo Tina,
    Wonderful article! You thoroughly answered my questions. I see that a soft cloche, not too embellished, with modest earrings will be perfect on me. Once I saw the models and illustrations, it was clear what would go with my over-all look as well as my face and hair. I especially adore that asymmetrical cloche!
    Thanks so much for sharing your genius,

  2. Zoraida Rodriguez

    I loved your article, I always loved hats, women in Puerto Rico do not wear hats, but I want to start the trend. I am 65 years young, short-short hair gray-blonde. I want to start with a red hat.....god bless

    • Tina-Boomerina


      I'm so happy you want to start wearing hats. When I was a little kid, no fashionable woman would go out without a hat (and gloves). But, I haven't started the glove thing yet... I may change my mind when I start getting brown spots from all the sun damage.

      Hats are so much fun. You need to try different styles until you find just the right kind, but cloches are one of the easiest hats you can wear. Once you find the right cloche, you will love hats with a passion. And, soon everyone you know will love hats. And, then you'll start branching out into fedoras and berets and newsboy caps and floppy brims and everything....


  3. Zoraida Rodriguez

    Tina: sometimes we find inspiration in the least expected places. When I thought of wanting to wear a hat, maybe is because I want to see me different . using a hat in Puerto Rico is a challenge, but I want to be honest I do not know how bold or brave I can be, getting out of the ordinary, wearing a hat...is pretty way of starting. I wish you many beautiful days in this year 2015, the year of the manifestation of things expected and prayed for.

    I would love to be in your newsletters and see the simple abundance in your everyday comments and support you give to all those wonderful, unique beautiful ladies out here .

    Be blessed,


  4. Louise Green

    Hi Tina,
    Thank you so much for using our photos on your blog.
    My friend just forwarded this to me.
    I love the idea of a boomerina!!
    PS Born in 1954 :)

    • Tina-Boomerina


      Hi. I have been using your photos for a few years now, ever since someone at your company gave me written permission to use your images.

      I have about 10-15 Louise Green hats in my closet and hope to add to my collection. So, I am a huge fan. People have stopped me on the street (from Seattle to LA to Paris) to ask me about whatever hat I was wearing that day. I always promote your website because I like your hats and I'm sure I would like you, a fellow Boomerina.

      I only push products I like.

      And, even though your toppers are a bit more than some of my other hats, I feel they are investment pieces I will wear for 20 years, and someday I will pass your hats on to my kids or potential grandchildren or step-grandchildren or someone I love. And, they will think of me.

      Your hats are well made and beautiful. When my daughters marry, I hope to come to your shop and have something made bespoke. Finding your site was a glorious improvement to my life. You rock!