Style Glossary: Hat-a-Girl! Headwear Through the Ages

If the recent royal wedding whetted your appetite for hats, you’re in luck – the U.S.’s most fabled headwear happening, the Kentucky Derby, is racing onto the radar this weekend! To help you show off your smarts as you get your ‘fill-y’ of fab hats at the Derby, I’ve done a little roundup of hats through the decades for you.

A special thanks to reader Jessica, whose blog comment inspired this post!

If you’re ‘re-greta-ing’ your lack of a Garbo hat or looking for a hat that will ring your bell, check out the vintage-inspired Never Felt This Way Hat, A Cloche Call, or any of the other cute hats abounding in the accessories section! Which hat style is your favorite?

About Hannah

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  1. Molly K. (ModCloth) 05/06/2011 at 3:59 pm #

    Trés adorable, Hannah! I think I need a Garbo hat in my life, STAT!

  2. Sydney 05/06/2011 at 6:25 pm #

    I wish I could pull off hats, but I just can’t. Every single hat I have ever tried has made me look utterly ridiculous. Plus, hat hair–who needs it? I think I’d rather have a pretty scarf or something.

    • Nez 05/08/2011 at 1:22 pm #

      I have been wearing hats since I was a very young lady. My mother insisted we always have our hair covered when out and about bonnets, hats, scarves, or even just a headband or clip!! Naturally I have pushed my friends to try hats even when they say they can’t pull them off. You just have to rock it find one you love and think looks half decent and then fake the confidence until you have it! Thats what I did as a teenager going to weddings with giant hats on!! feeling like a total dork!! Believe me once your hooked you won’t be able to resist.

    • brittany 05/14/2011 at 9:47 pm #

      Same here! I love vintage hats and have quite an extensive collection, and I’d like to wear them, but I look sooo bad in hats… I think it’s my small head, maybe.

  3. Diana 05/07/2011 at 1:45 am #

    Every girl should have a great hat!!

  4. Wendy from Wendys Hat 05/07/2011 at 3:41 am #

    Love this and love a great hat!

  5. Michelle of The Feather Den 05/07/2011 at 9:49 am #

    I *need* a cloche in my life.

  6. Emily 05/07/2011 at 11:10 am #

    Not only do hats make a great accessory, but they also provide a quick fix to bad hair days! I love the Cloche and Garbo.

  7. Charlotte 05/07/2011 at 1:24 pm #

    I personally adore cloches. But I have a small head and can never seem to find ones that don’t completely obscure the vision.

    I do love pillbox hats too but only when they have veils and such attached.

    • Heather 05/09/2011 at 9:17 am #

      I’ve got rather a small head as well. If you can find true vintage hats, they usually are smaller (hat sizes 6 to 7) than modern ones!

  8. LilyT 05/07/2011 at 1:25 pm #

    Finding the right hat can be frustrating but all it takes is just one! I have a straw cloche hat with a simple black ribbon around it that I get non stop compliments on!

  9. Elissa 05/08/2011 at 1:04 am #

    I never thought to look it up before to double-check, but in fashion school they taught us that “cloche” meant “clock”. Fail. It does mean “bell” and also “goofy”; I just checked.

  10. Jo - Lost in the Haze 05/08/2011 at 6:02 am #

    I love love love cloche hats! When I wear a cloche hat, all I want to do is put on some pretty Mary Jane heels and drape pearls around my neck!


  11. Heather 05/09/2011 at 9:19 am #

    I’m so pleased to see this post! I adore hats and have a small collection! Every face has at least one style of hat that compliments it!

  12. Karen 05/10/2011 at 12:30 pm #

    LOVE Hats! I find myself gravitating to cloches more (I have like 5 haha), but am trying to venture out towards diff styles. currently stalking a vintage porkpie derby (civil war era) on ebay…also can’t wait til ModCloth restocks the Up in the Antique Hat!! Please please buy more soon!

  13. Carol 05/13/2011 at 10:49 pm #

    Love the hat. You look great. I’ll have to explore the possibilities of hats out there. Thanx!

  14. Jean 05/15/2011 at 1:21 pm #

    The 60’s!

  15. Alenza 07/15/2019 at 4:58 pm #

    I love to wear these hat’s

  16. harvey edward 12/30/2019 at 2:57 am #

    I really love these hats and look really cool.

  17. Lillydaplyn 01/23/2020 at 9:54 am #

    Awesome collection!

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