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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.red flapper hat 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, but live in fear of wearing the wrong hat into the main dining room? It just boggles my mind.flapper hats

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:

  • 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.
  • 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? can a woman wear a man's hat?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.)
  • Does my hat have to match my outfit? It doesn’t matter. It’s more important for the color of your hat to look good with your skin tone.
  • 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.

  • 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)

Keep reading about different kinds of hats on page two.

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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....


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