15 Tips For Pulling Off A Kentucky Derby Hat, According To Celebrities


The Kentucky Derby is in full swing, which means they’re rolling out the enormous hat boxes. In case you want to put on your own hat for the event, we’ve put together 15 tips and tricks from celebrities to make everything a bit clearer when it comes to the confusing world of hat wearing. Let’s take a look at some of the best Kentucky Derby hats celebrities have turned up in over the years, and apply their methods to our own heads.

1. Pick a hat that hides your eyes and is funeral appropriate

Jeff Gentner/Getty Images

Jeff Gentner/Getty Images

Kim Kardashian’s 2009 is pretty subtle for her

2. Pick a hat that goes well with a prop


Jeff Gentner/Getty Images

You’ll want to practice your posing, and Bethenny Frankel displayed an excellent use of the lollipop prop for perfect photos in 2009. Just make sure your hat matches whatever sexy-baby prop you pick.

3. Be bold. Be fearless.


Michael Loccisano/Getty Images

Kate Gosselin‘s 2011 hat might win the day when it comes to bold originality. I’m not even sure how that qualifies as a hat. Just fantastic.

4. If you’re short on embellishments, wad up some toilet paper

Michael Loccisano/Getty Images

Michael Loccisano/Getty Images

Pinterest almost certainly has tutorials for making toilet paper rosettes like Coco used in 2012.

5. Show some patriotism, but not too much


Michael Loccisano/Getty Images

Debra Messing‘s 2012 look from Hot Topic Americana shows that USA and H.I.M are tied for #1.

6. Steal an antique doll’s hat if you’re short on time


Jeff Gentner/Getty Images

When time ran out on Melissa Joan Hart in 2007, she ran into the American Girl Store and swapped a hat off one of the Victorian life size dolls. It looks lovely.

7. Size matters


Joey Foley/Getty Images

Cyndi Lauper showed the entire Derby who’s boss in 2012.

8. Wrap yourself like a present. Coordinate your gloves.


Mike Simons/Getty Images

Anna Nicole Smith was all wrapped up in 2004, and you can DIY your own by sticking old ribbons and bows to a visor. Rest in peace.

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    • Samantha Escobar

      Am I the only person who is SO CONFUSED as to how some of these people get invited? Good gracious.

      Also, #7 forever. <3

    • Lindsey Conklin

      Kim K, JSimps and Paula Patton look awesome. I do not look good in hats!

    • Kay_Sue

      I want a Derby hat…

    • Jenni

      Ahh that photo of Debra Messing!

    • J_Doe5686

      I want to wear one of those hats. It looks so cool and fun!