I am definitely a classic hat kind of girl. Give me a traditional Panama or a dapper grey fedora, and I’m happy. But as I’ve filled out my hat collection, and covered all the basics, I’ve got a hankering for a little more of an exclamative topper for my temples. A year ago, I would have gaped at these picks, but now I’m totally digging the quirky expression of these stylish hats.

1. Blaine Hat – Pearls on a hat? I think I’d have thought you crazy, but I actually adore the combination of structure, fabrics, and color on this fedora. It’s got a subtle western feel, but would be right at home for a night out in New York City.

2. Ashland Corduroy Newsboy Hat – Early this year I was a bit on the fence about newsboy hats, but you know what? I love Newsies, so I’m ready to embrace the trend and seize the day (Newsies joke) on this corduroy topper. Don’t you love the color?

3. Essex Bucket Hat – The chicest way to wear a cloche-like bucket hat. The color is superb for fall, and the wool shell will keep your head warm come fall!

4. Drake Hat – I absolutely adore this brushed felt, ribbon tied hat. It would be much at home in a Jane Austin BBC drama, and the color is divine for the cold weather of autumn and winter. Get in my shopping cart!

5. Fiddler Cap Hat – This hat transports me to the 1970’s and backstage at a Rolling Stone’s concert. It’s that cool. (P.S. It is on sale for $11!)

6. Ana Cap – A modern looking riding hat in a delicate dusty rose. Such a different look, but oh so eye-catching!

7. Maureen Beret – I usually don’t like polka dots, but this eye-catching beret is in my favorite color combination.

Which one would you dare to wear?

Do you wear hats or have any cap related questions? If so, be sure to share your thoughts with me in the comments below!