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Best Hat Styles for Women With Short Hair (updated)

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Cloches Always Good


A Cloche Hat Is Always Good With Short Hair

Without knowing anything about you or your haircut, I would suggest you try a cloche. If you look good in short hair, you will probably look good in a Gatsby-style flapper hat. And, since 20’s deco styles are terribly fashionable right now, you should have no problem finding a cloche you like with a price you like.

Note: If you are shopping online, try an inexpensive cloche as an experiment. And, inexpensive is relative… I have some hats from Louise Green that were over $300. Inexpensive means a $30-ish dollar hat from Nordstrom’s or some site where you can send your hat back - with no restocking fee - if it’s not right. Hey, unless you get lucky, a decent hat is more like $100 and up… the shaping and quality will be obvious. Soon, you will be eating Top Ramen so you can have a ton of hats in different styles from the top milliners, like my favorite - Louise Green.

Cloche hats (with their bell shape) are an extremely versatile style. A straw cloche is great for summer excursions or for evenings at restaurants. A felt cloche is perfect for tarting up your wool coat in winter or for lunching with the girls. And, cloches can be dressy or casual like this Downton Abbey hat with an upbrim.

What Kind of Jewelry Should I Wear With a Cloche?

The type of jewelry you should wear with your cloche depends on how you want to look… and earrings are the main consideration when thinking about jewelry and hats.

hats for long hair or short hairOf course, I would not recommend gigantic boho dangles with a cloche, but I’d have to see the overall effect to make sure I’m giving you the right advice. If your cloche has large embellishments (like a cabbage rose or a huge bow), you might be able to wear large earrings. However, you might not look right in hats with huge cabbage roses if you have a small or narrow face or you have a small or slender physique. So, there is no simple answer… it’s all about balance. And, it’s all about not overdoing it, but not wimping out and underdoing it like a little mouse.

Best Earrings for Cloche Hats

It’s easier to explain what earrings to wear if I show you photos:

Gray Cloche with Flowers: This hat would look good with small pearl studs or small mabe pearls or something unobtrusive like that. Add a necklace if you want, but don’t overpower the femininity of this hat.

Gatsby Style Hat: Flapper gals generally wore small or long, dangly earrings. You can take your cue from them. On the other hand, I do not have delicate features, so I wear my huge mabe pearls with my cloches because my face is round like the Campbell’s Soup girl.

Casual Cloche With Drop Earrings: This model is wearing simple, but long teardrop dangles. And, her hair is tucked up under her hat. Who knows if her hair is long or short?

If your cloche is small (close your head), you can wear long, thin, dangly earrings for a trendy nighttime flapper look (or daytime look if simple). And, if your cloche is voluminous, you can wear something like the earrings in this vintage 1920’s art deco illustration.

Other Small Brimmed Hats: Fedoras, Buckets & Mod Caps

If you want something less frou-frou, consider one of these styles:

wear fedora with stud earringsPurple Fedora (photo on right): Fedoras are menswear, so they look best with button earrings, pearl studs, CZs, small hoops, and any jewelry you would wear with tailored clothing. Try your fedora worn front, back, tilted, and any-which-way-but-loose until you find the best angle for your face and your haircut. Unless your face is very feminine or your hat is a bit girly, you should probably show some hair with your fedora. Note: Do not wear your fedora with excessively big earrings or hoops, or I will send you to the back of the line.

Bucket Hats for Women: A bucket hat is like a cloche but it has a squarer crown. In my opinion, bucket hats generally look best with longer hair, but if you can pull your hair forward to soften the look or if you have a very feminine face, this might be a good style for you… and bucket hats are always good as casual toppers for the beach or the pool. Wear the same jewelry as with a fedora.

Mod Caps for Women: Mod is very geometric and this hat (or something similar) would look better on a woman with shorter hair or a sharper cut. Mod caps are worn with geometric earrings… try big colorful buttons or large hoops. Look at old photos of Twiggy and Patty Boyd to learn how to wear a Carnaby Street cap. But, 60’s caps look great with jeans and T-shirts, as well as with dresses. You’ll see other caps similar to those that we wore in the 60’s, but I wanted you to see how wrong this hat looks with this model’s long hair.

Note: Do not confuse a Mod cap, a newsboy cap, or a schoolboy cap with a trucker or baseball cap. Trucker hats and baseball caps are not fashion statements.

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Whimsy Hats & Fascinators

Evening, Pillbox & Whimsy Style Hats:

Whimsy hats are what you wear in the evening with a cocktail dress or party dress. Well, your other option would be to wear your tiara, but who wants to go through all those other tiaras in the vault to find the right one. Sheesh. After a while, those diamonds all look the same. It's just so much easier to wear a headband fascinator or a whimsy headpiece. (Actually, the gray hat in the center above could also be worn for daytime with a gray skirt-suit. Very 60s chic.)

Oh, no. This article is getting ridiculously long... well, that's what happens when I start yakking. I’ll have to tell you about hats with bigger brims in another article. Look at some of the other articles... you may find the answer you seek.

More Articles for Baby Boomer Women:

How to Wear a Hat: Rules & Etiquette for Women

Types of Hats for Women and When to Wear Them

13 Accessories Trends for Spring and Summer

Photo Credits: All hats except noted below from Louise Green with permission.

  • Your Hat Need Not Match: Rust fedora: Modcloth.com. target="_blank">Modcloth.com. Bummer. Sold out.
  • Black Cloche and gray whimsy beret: Debanham England.
  • All of the expensive cloche hats are at louiseGreen.com.

    The Best Sunhats for Women (This article helps with sunhats.)


    What do you think of this article? Leave a message at the bottom of the page. Let me know if you're a hat freak, too.

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!