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Types of Hats for Women & When to Wear Them: Fedora, Cloche, Victorian & More

Different Ladies Hats

by Tina Boomerina (Christina Gregoire)

What kind of hat should you wear in fall? In winter? In spring? In summer? There are so many different types of hats: fedoras, cloches, Victorian Steampunk, evening hats and more...and all of you women will have fun with all of them.

This article has been updated with several new photos. And, even though many of these hat pics were shown here a few years ago, almost all of them are still available. And, a few of these toppers are brand-spankin-new for spring and summer 2015.

read about how to wear a hat and when

Hat Tips for Women

Why do women who are normally forthright, assertive, and self-assured find themselves groveling for advice about buying hats? Yes, there are some rules about wearing hats and about taking them off, but most of those rules apply to men. Ladies do not have to worry that the hat police will come by and order them to cram those offensive toppers into their handbags or go to jail.

What Kind of Hat Do You Want?

There are girls and women who seem perfectly happy to show complete strangers their umbilical piercings and tattoos, and to hint about having more, but they are afraid to don simple fedoras like their favorite celebs wear.

And, what about all the older ladies, who think nothing of showing their flamboyant rolls of fat to everyone walking past the cruise-ship pool... and then they live in fear of wearing the wrong hat into the main dining room?

It just boggles my mind.

Hat Rules for Women

Here are some general rules of thumb and answers for women who want to be trendy but don’t really know how to wear a hat.

read about different types of hats

Cloche Hats: Winter & Summer

Click on links to see examples of different hats:

  • 1 Sun hats with big brims are worn when it’s warm and you want to shade your face from evil wrinkle-producing rays. Pinks and blues are good colors for most women.
  • 2 Straw hats and other lightweight hats are worn during summer or whenever a warm hat is not needed. For example, there is nothing wrong with wearing a straw fedora year round in Southern California.
can a woman wear a man's fedora? read tips

Women's Fedoras

  • 3 Can a woman wear a man’s fedora? Yes, but men’s rules apply to fedoras and cowboy hats in most circumstances.  Fedoras (and other masculine hats), which are majorly girly with embellishments like flowers or netting are exempt from men's rules and may be worn at table and throughout the National Anthem. (Lady's prerogative.)
  • 4 Does my hat have to match my outfit? It doesn’t matter whether your hat matches your outfit. It’s more important for the color of your hat to look good with your skin tone.

  • 5 What kind of hat should I wear? A cute hat. An elegant hat. A trendy hat. Any hat that doesn’t make people fall down laughing. This photo shows a combo you should not wear.
  • 6 When should I switch from spring/summer hats to fall/winter hats? When the weather starts to feel cold. Note: Don't laugh at this question...many women have asked me this. Common sense rules ladies hat rules. You probably shouldn't wear this hat if you are over 40 and your kids might put your photo on Facebook. (article continues... so keep reading)
read about different hat styles

Victorian Top Hat

Women's Hat Etiquette & Rules

Do women have to follow hat rules? No, not really. There aren’t any hard and fast rules about ladies’ chapeaus just like there aren’t any hard and fast rules about when a woman should wear a coat or blazer. Who starts fashion trends? People who look at clothing and say to themselves, “Wow, I wonder what I would look like in that?” or, "I wonder what this cool thrift-store dress would look like with my new menswear fedora?"

read about hats & when to wear

What Are Different Names of Summer Hats?

Spring/Summer Hats for Women

Here are some inspirational chapeaus. Hats can be a fabulous accessory and also a cheap way to make a plain T-shirt and blue jeans look cool. Any lightweight hat, of any shape, can be worn in warm weather.

  • 1 Giant Sun Hats: Hats with large brims may be worn (inside or outside) during daylight hours. There are floppy hats made out of felt for cold winter weather.
  • 2 Cloche Hats: Cloche means “bell” in French. Some people call this a flapper hat but some cloches have different brims or no brim at all.
  • 3 Paperboy Hats: These are also called newsboy caps. Imagine a little kid on the sidewalk selling newspapers in a vintage movie.
  • 4 Mod or English Schoolboy Caps: In the 60s, this shape was de rigueur Carnaby Street style.
read about felt woold hats for women and more

Women's Fall Winter Hats

Fall/Winter Hats for Women

Fall or winter fashion hats are usually made of felt, though knit hats and fur hats are popular, too. Any of the summer hat shapes can "become" fall/winter hats if they are made from heavier fabric.

To me, the phrase "winter hat" usually means a sporty outdoor ski hat, velour hat, fleece hat, or fur hat. Actually, the only real difference between a winter sport-style hat and a fall fashion hat is that a fashion hat cannot be worn, for long periods of time, in rain or snow. Fashion hats must be reshaped or reblocked if they lose their shape due to excessive moisture.

read about adaptable evening hats

Some Evening Hats Work for Daytime

  • 1 Victorian Top Hats: This photo (in the link) is from my fave hat shop - Louise Green. It's perfect for steampunk outfits, and boho brides are wearing top hats instead of veils.  (The hat in the main photo for this article is also Victorian. This style would have been worn when you rode sidesaddle at your country house...of course.)
  • 2 Cloche Hats: Notice that this is the same shape as the summer cloche. The main difference is that this hat is made of felt.
  • 3 Pork Pie Hats: Pork Pie hats were invented during the Victorian age.
  • 4 Beret Hats: Knit or wool berets are for winter, but lightweight berets can be worn in summer. Some berets are made out of cotton and others have sequins, which would make them perfect for parties and clubs.
  • 5 Ladies Fedoras: A fedora was originally a man's hat, so fedoras are perfect for women's suits, but lots of Hollywood celebs wear these hats with girly dresses.
read when to wear different kinds of hats

Some Hats Look Best in Evenings

Women's Hats for Evening

Here are three types of hats that are commonly worn with dressy cocktail-party ensembles or long ballgowns. Some fascinators can be quite elaborate, but women who are not used to being in the spotlight should probably stick to simpler styles. After growing accustomed to unknown people coming up and saying, "Oh my God, I love your hat," hipsters can graduate to the big leagues.

  • 1 Cocktail Hats: With a veil or without, cocktail hats can be worn during the day, and (of course) they can be worn with cocktail dresses and evening dresses.
  • 2 Mini Top Hats: Perfect for Steampunk, as well as evening wear, mini hats (also called doll hats) are uber trendy these days.
  • 3 Fascinators: Most fascinators seem to come on headbands and most of them have feathers, flowers, or netting.

There are more styles of hats, but these are some of the trendier ones. Various parts of the world give different names to the same hat. For example, a bowler (UK) and a derby (US) are the same thing. Lucky girls and women can have something custom made and then they can call their hats anything they like.

More Articles for Baby Boomer Women:

Sexy Plus Size Cruise Wear: Cocktail & Formal Dresses


Paris Street Style for Women Over 40 or 50


Hippie Wedding Dresses for a Casual Bohemian Chic Celebration


Animal Prints for Women Over 40, 50 & 60

Photo Credits: Louise Green (with permission) and prshots.com

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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. June

    I was fortunate to be gifted an extraordinary collection of vintage hats. Fabrics range from straw to felt to wool and styles from cloches to fedoras. Now I have a hat for just about every occasion. Your blog proved most useful and inspiring. Thank you!!

  2. Cindy

    Can a woman over 50 wear a fedora without looking ridiculous? I love the straw for the summer and wool for the winter but I'm just not sure if I can pull it off....

  3. Brim-ful of Asha | dramatizebyaamra

    […] or jeans with a derby hat. Ensure the hat is intune with your look. Experiment and don different  hats and face- […]

  4. Chae

    Thank you so much! I am a fledgling hat maker and am making my first cloche!

    • Tina-Boomerina


      OMG, I have always wanted to learn how to make hats (or just embellish a plain hat), but I'm so klutzy that I've never tried.

      I hope your cloche turned out great. I hope you become a famous milliner. And, even if your first try isn't what you wanted... keep at it. There are very few REALLY good (and I mean flattering) hats online. I don't know how long it would take to get the hang of it, but most good hats cost a fortune, so keep at it... and make money. And, the world needs more hats. I would love to find a site with good, but simple cloches, fedoras & floppies that could be embellished with different colored hatbands and/or flowers... so women like me (who can't embellish anything) could order a hat with a certain color trim.

      Just a thought... if you really get into this. I swear... if I could use a glue-gun without burning down the house, I'd keep making hats until I became famous. Go for it.