Kentucky Derby
September 03, 2020

Kentucky Derby 2020 hats you can also wear on the golf course

Celebrating the Kentucky Derby at the end of the summer rather than the first Saturday of May feels a little different this year—but that doesn't mean you can't go just as big as you normally would. You can still wear that hideous pastel shirt hiding in the back of your closet. Though no fans will be in the grandstands of Churchill Downs, what better way to pay homage to the famous Triple Crown race by wearing an absurd hat, typically found on fans attending the races. We rounded up our favorite derby-themed hats ... why not switch up your headwear rota when you head to the golf course this weekend for something a little more equestrian?

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RELATED: Everything you need for the perfect Kentucky Derby celebration this weekend
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Let's begin with a relatively simple cap. A solid baseball hat is a great way to show your Kentucky Derby fandom without having to worry about the statement taking over your look. The dependable curved cap look is timeless and there are a ton of unique logo designs to choose from.

For a slightly louder statement, all-over printed caps are very on-trend in golf. Two of our favorite Derby-themed caps this year are the '47 Kentucky Derby 146 Jockey Silk Adjustable Hat ($30) and Vineyard Vines Patchwork Whale Dot Trucker Adjustable Hat ($34) with designs inspired by the unique jockey silks worn at horse races. Be a little more mindful when incorporating a printed cap into your on-course look and stick with a simple outfit to avoid clashing.

If you're looking for something with even more personality or want to feel like you're actually at Churchill Downs, a straw hat is a great option. The golf headwear favorite is also a traditional Derby staple. The appropriately named Walter Hagen Gambler Hat ($24) is great for those putting a bit of change down on the race this year—and the added sun protection won't hurt either. For the ladies not ready to go full straw, a braided visor is a great option to try out.

The Kentucky Derby-themed options are vast, flat brim and visor fans can play along as well. The '47 Grandpa Visor ($30) is a tour-worthy throwback look that's easy to pair with other looks. And the Imperial Keenland Retro Patch Rope Cap ($26) celebrates Kentucky's also famous Keeneland track, which Kentuckians can attest is full class.

This wouldn't be a hat roundup without a few controversial bucket hats. From the simple Five Running Horses Bucket Hat ($14) to the majestic Wild Horses Bucket Hat ($10), this weekend may be the time to try (or win) the trend. The top tip for pulling off a bucket hat? Blind confidence and preparedness to block out the haters.

If you've gotten to this point and are still looking for something more extravagant to wear this weekend to celebrate the Kentucky Derby, buckle up. We consulted our in-house expert and as usual, his picks were equal parts opulent and outlandish. We can't promise these fun caps will improve your game, but you certainly won't be ignored if you wear one. They'd also make the perfect gag gift for your golf buddies who seem to have everything.

Over to Greg Gottfried . . .

Unfortunately, unless you’re Wes Welker, you most likely will never go to the Kentucky Derby live. However, since you’re reading this on Golf Digest, there’s a very good chance that you’ll be going to a golf course this weekend. So, live a little. Wear a ridiculous/awe-inspiring hat and impress your friends and enemies alike.

Okay, here’s a scenario... You’re on the 13th green and the sun is beating down on you. You’ve run out of water—for some reason you only brought one bottle—and the food and beverage cart is nowhere to be found. The sweat on the back of your shirt resembles a Rorschach Test. What do you do? Well, if you were smart and wore your cap with a fan attached to the top, you would be doing just fine. With a hole letting air through, this is an ingenious design that deserved a Nobel Peace Prize and it could be yours for less than $24.

The name says it all here. This is a “crazy” hat ($10). It’s also perfect and I wish I had three of them. You’re not getting any more Kentucky Derby x Golf headwear than this one right here. You can even move the golf ball around with a string tying it to the flag centerpiece. If you’re looking to wow, don’t go any further. This is it.