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
Kim Kardashian’s 2009 is pretty subtle for her
2. Pick a hat that goes well with a prop
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.
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
Pinterest almost certainly has tutorials for making toilet paper rosettes like Coco used in 2012.
5. Show some patriotism, but not too much
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
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
Cyndi Lauper showed the entire Derby who’s boss in 2012.
8. Wrap yourself like a present. Coordinate your gloves.
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.
9. Rosettes always require a some netting to keep things in place
Place it to the side like Mary J. Blige in 2012 and you’ll look like a jaunty, floral Peter Pan.
10. If you’re going to go food-inspired, go for a cupcake.
Miranda Lambert looks freshly baked and frosted.
11. Try an artistic statement
Paula Patton‘s 2011 choice looks like a nice seascape painting hanging on a gynecologist’s waiting room wall.
12. Don’t be afraid to be inspired by female anatomy
Lauren Conrad‘s flesh colored folds double as a health class model.
13. Match your hat to your husband’s lip gloss
Seeing Jessica Simpson‘s 2004 look perfectly complementing Nick Lachey‘s mouth is just too sad for those of us with tender hearts.
14. Don’t feel pressured to wear pastels
There’s no reason to limit your color palette, and Johnny Weir‘s 2010 look is some solid inspiration. The flying saucer of his hat is nicely offset by that frayed blazer.
15. Consider matching your hat to your bronzer
If you’re going for a fake tan à la Tori Spelling in 2005, you should highlight your new skin tone by matching your hat to it.
With these tips and tricks from our finest fashion icons, you’ll be the talk of the town.