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Finally, here comes the season for mint juleps and rose garlands. It’s time to bring out those classic bourbon cocktails and delicious barbecued meat to feast on.

For as the horses run free on the racetracks, so too comes the opportunity to wear your most fashionable and dashing hats ever.

The annual Kentucky Derby is the most celebrated horse race in American history. But other than being a sport, it’s actually more of a fashion show. And hats are the guaranteed center of attention.

Some may think that wearing hats during Derby is strictly a ladies’ business, but that’s not how it is nowadays.

In fact, Derby season presents so many choices for men to dress up that you may get a bit overwhelmed — from ivy caps, straw fedora, to bowler hats. But, worry not, because we got you covered for this year’s most stylish Derby hats.

So without further ado, we have rounded up the best Kentucky Derby hats for 2021 just for you. You can finally start this year right by revamping your wardrobe.

Read on to become this year’s most fashion-forward Kentucky Derby fella!

The Classic Derby Bowler Hat

Nothing beats the original. There is a reason, after all, why it’s also called the Derby Hat.

Bowler hats are sturdy, bulbous hats with short, rolled brim and a small grosgrain band. Although Kentucky Derby trends almost always differ every year, bowler hats still draw from timeless and original traditions. 

These hats are made famous by popular sophisticated gentlemen – actors, artists, and writers who have a mysterious sartorial flare.

But if you’re not into all that and just want to spend the day grilling meat under the sun, then you can pair this hat with a washed denim jacket and leather pants. Put on chunky cowboy boots and a beater shirt. Tilt the bowler hat slightly and ultimately finish it off with lit tobacco.

That’s the signature laidback style.

The Gambler Hats

The gambler hat is known for its medium-length brim and short crown height, which makes it a stylish alternative for those who do not like the wide-brim “cowboy hat” style.

These hats are your go-to solutions to look formal and chic while giving off casual and laidback vibes during Derby days. These show off a modern and sleek touch to the traditional southern American style.

Gambler hats are just perfect for Kentucky Derby because it’s an elegant alternative for the typical cowboy hat if you’re not up for all that.

Imagine a cross-off between the sophisticated Rhett Butler from Gone with the Wind and the hip-hop suave artist Justin Timberlake – this is the guaranteed aura you’ll emanate from wearing gambler hats. 

Arrive in food festivals and bars wearing these and you’ll surely draw admiring glances in your way.

The Fedora Hats

Fedora hats are timeless pieces. They are stylish and fashionable, something that puts you up there with Frank Sinatra, Al Capone, and Michael Jackson. If you want to celebrate the Kentucky Derby looking like a rock-and-roll singer or an action star, then the fedora hat is yours to wear.  

The fedora is known for its flexible and soft brim and its lengthwise crease down the crown, “pinched” by both accented sides.

These hats are versatile and easy to style because they can fit almost every occasion. It’s more casual and adaptable than a bowler hat, yet more formal than an ivy cap and flat cap.

It is best paired with a suit jacket, blazers or overall coats. Highlight its vintage style with cowboy boots and leather gloves, and you’re good to go.

From the sidelines to the muddy tracks, Fedora Hats will protect you from the sun without sacrificing your style.

The Straw Boater Hats

Some men are reluctant to wear straw boater hats out of fear that they would look out of place and too casual. After all, Kentucky Derbies are more or less demanding of elegant fashion.

However, if matched together with the right styling and confidence, these hats can score you your coolest Derby get-up ever.

Straw boater hats’ most prominent features are their elliptical shape and flat brim and a flat crown, also known as the ‘telescope crown.’ It usually has a solid or satin grosgrain ribbon that wraps around the entire crown.

Truth be told: straw boaters hats are not always the best protective choice for the sun due to their short brim. Nonetheless, they are easy and breathable to wear and a quintessential need for the hot weather.

Although these hats can blend well with almost everything, it’s usually worn with silk polo or light linen suit. Don’t go overboard, and just trust your fit!

These relaxed hats will assure you that you’re simultaneously comfortable enough to drink and have a good time in a muddy paddock with rodeo friends and still look fine when you’re up in the stables with the horses.

The Pork Pie Hats

Love it or hate it, the porkpie hat will always be a staple for Kentucky Derby events.

Its unique shape may have come as a visual shocker to some, but it has definitely created a statement among partygoers. And since Derby only happens once a year, why shy away from making a bold appearance?

Porkpie hats are flat hats with slender upturned brim known as “stingy brim”. Another distinguishing element is its narrow, round-shaped crown.

Although short and small, this hat is big on style. Recently the tip of these hats is often printed with loud, colorful patterns and a simple sewn edge.

To have that ultra-sleek urban get-up, style this pork pie hat with a slim fitting black suit. Wear your leather boots and add an extra accent with some clean white tie and you’re all decked out for the Kentucky Derby fashion show.

Now that you know which hats are best to wear for Kentucky Derby, it’s time to actually cop it.

You can browse our curated selection of various men’s hats to find the perfect headpiece to make this Kentucky Derby your fashionable year ever.

Frequently Asked Questions (FAQs):

When is this year’s Kentucky Derby?

It will start this April 30 and will end on May 1. Although some events will be a bit subdued due to the pandemic, nothing can stop the Louisville spirit! 

Will people still dress up for Kentucky Derby?

Spring fashion is a long-held tradition during Derby. Some may think that wearing hats during Derby is strictly a ladies’ business, but that’s not how it is nowadays. Pair up your facemask with a stylish hat and you’re good to go!

Where can I find Kentucky Derby hats?

Now that you know which hats are best to wear for Kentucky Derby, it’s time to actually cop it. You can browse Dapperfam’scareful selection of men’s hats to find the perfect headpiece to make this Kentucky Derby your fashionable year ever.

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