Kentucky Derby Style Guide: From head

The 150th Kentucky Derby is set to take place this Saturday, May 4th, in Louisville, Kentucky.

The annual competition is not only a prestigious horse race but a fashion spectacle with a very unique and special dress code. Whether you'll be watching from the stands at Churchill Downs or attending a Derby-themed party, it's not a bad idea to start planning your outfit.

'A smart look at the Kentucky Derby is all about embracing the tradition of the event with a modern twist,' says Suitsupply founder and CEO Fokke de Jong.

The 150th Kentucky Derby is set to take place this Saturday, May 4th, in Louisville, Kentucky

The annual competition is not only a prestigious horse race but a fashion spectacle with a very unique and special dress code. So whether you'll be in the stands of the Churchill Downs or attending a Derby-themed party, you'll need to start planning your outfit

The Kentucky Derby has a rich history dating back to the late 19th century, and is one of the most prestigious horse races in the world.

Founded by Meriwether Lewis Clark Jr., grandson of William Clark of the Lewis and Clark Expedition, the race was inspired by horse racing events Clark witnessed in Europe. 

The first Kentucky Derby was held on May 17, 1875 and its attendance continues to grow year after year, attracting spectators from all over the world.

Dressing up for the derby has become a longstanding tradition that adds to the excitement and glamour of the exciting event. 

Outfit ideas for the dapper gentleman

Wear a jacket 

'The key to a smart Derby look lies in the details: a well-fitted jacket, a pop of color, and the confidence to carry it all with effortless style,' says Suitsupply's Fokke de Jong

Rain or shine, hot or cold, it is imperative that you appear pulled together for this race.

'A jacket is certainly recommended to complete the look, especially in a more bold color or pattern,' says the expert.

Chris Pine attended the Derby last year in a light blue single breasted jacket paired with white slacks.

The 'Star Trek' actor added interest to the sleek look with a navy tie and a printed pocket square.

Chris Pine attended the races last year in a light blue single breasted jacket paired with white slacks. The 'Star Trek' actor added interest to the sleek look with a navy tie and a printed pocket square

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'We’re seeing an inclination towards pastel hues and vibrant colors, which are perfect to wear for the occasion. A good example is our double breasted Light Pink Tailored Fit Havana Suit, and single breasted version,' said Suitsupply founder and CEO Fokke de Jong

Additionally, for those who prefer a more subdued palette, our Light Taupe Checked Roma Jacket and Navy Checked Havana Blazer are an excellent choice, providing a refined yet relaxed look while still fitting in with the Derby day spirit'

Opt for a lightweight fabric

Temperatures in Louisville in early May can vary but the forecast this weekend calls for a high of 86 degrees.

'The ideal material for the Kentucky Derby should balance style with practicality,' shares the expert.

'We suggest a lightweight and breathable fabric that maintains its appearance throughout the day such as a blend of wool, silk, and linen, perfect for staying cool under the sun.'

Stick to soft colors

Pastels are always on trend for spring and a favorite at the Derby. 

'We’re seeing an inclination towards pastel hues and vibrant colors, which are perfect to wear for the occasion,' says Fokke.

'A good example is our double breasted Light Pink Tailored Fit Havana Suit, and single breasted version.

'Additionally, for those who prefer a more subdued palette, our Light Taupe Checked Roma Jacket and Navy Checked Havana Blazer are an excellent choice, providing a refined yet relaxed look while still fitting in with the Derby day spirit.'

Don't leave home without your accessories 

A well-styled look includes accessories that are both fashionable and functional.

'A Panama hat or fedora can protect you from the sun and add a classic touch. 

'A linen pocket square can add a pop of color can elevate your outfit's sophistication.'

Choose the perfect shoe

While the prestigious race lasts only 2 minutes, you'll be standing on your feet socializing for much longer. 

To be comfortable without sacrificing on style, the expert suggests a pair of loafers, such as Suitsupply's Dark Brown Penny Loafer in Italian Calf Suede or Black Loafer in Italian Calf Suede.

Country music star Carly Pearce turned heads in a light blue dress with a three-dimensional floral skirt, made complete with a fascinator boasting the same florals

When it comes to head adornment - the bigger, the better! Be it a hat or fascinator, your headwear is the star of the show so the rest of the outfit should be styled around it

Outfit ideas or the ladies

It's all about headwear 

When it comes to head adornment - the bigger, the better! 

Be it a hat or fascinator, your headwear is the star of the show so the rest of the outfit should be styled around it. 

A large hat is a smart option, as it will not only add a dramatic touch, it will shade your face from the sun's damaging rays. 

To balance a sizable hat, opt for simple attire in a streamlined silhouette.

Play with color 

Style your hat with bold separates in complimentary colors à la American correspondent Robin Meade.

For a day at the races, the star paired a fitted yellow sheath dress with a purple hat featuring cascading orchids, creating an exciting and unexpected color combination.

Coordinate your hat to your dress

Country music star Carly Pearce and Meteorologist Dylan Dreyer both wore hats that matched their dresses perfectly in Louisville.

Carly turned heads in a light blue dress with a three-dimensional floral skirt, made complete with a fascinator boasting the same florals.

Dylan brought the print of her dress alive with larger-than-life flowers in the same shades on her hat. 

Dress comfortably 

The derby is as much a social event as it is a sporting event so you want to wear something you'll be comfortable in all day long. 

Actress Victoria Justice ditches a dress for a powerful pantsuit to attend the derby several years ago.

The former Nickelodeon star looked chic in a white set accessorized with a black hat and matching handbag.

When it comes to footwear, wedge sandals and kitten heels elevate your style while being kind to your feet.

Style your hat with bold separates in complimentary colors à la American correspondent Robin Meade. For a day at the races, the star paired a fitted yellow sheath dress with a purple hat featuring cascading orchids, creating an exciting and unexpected color combination

Kansas City Chiefs quarterback Patrick Mahomes and wife Brittany walked the red carpet at the 149th running of the Kentucky Derby on May 6, 2023, looking picture perfect

Couples coordination

Show your union in the same shade

There's no better time to coordinate with your significant other than at the Kentucky Derby. 

Sofia Pernas and Justin Hartley attended the 149th Kentucky Derby at Churchill Downs wearing deep red.

Justin's suit matched Sofia's dress and hat perfectly. 

Flirt with patterns that work well together

Rather than wearing the exact same clothing, your partner can incorporate a color or pattern you're wearing into their outfit. 

Kansas City Chiefs quarterback Patrick Mahomes and wife Brittany walked the red carpet last year looking picture perfect.

Patrick sported a plaid jacket with a light purple dress shirt and accessorized with a  printed tie and light pink pocket square, while Brittany donned a purple and pink tweed dress similar to the football star's tie.

The influencer and mom of two accessorized with a pink hat decorated with flowers and pearls.

Father daughter duo Dannielynn Birkhead and Larry Birkhead attend the derby every year in coordinating ensembles.

Coordinate with accessories 

Father daughter duo Dannielynn Birkhead and Larry Birkhead attend the derby every year in coordinating ensembles.

Last year, Anna Nicole Smith's mini me donned a voluminous ball gown featuring a large sunflower.

Her signature blonde tresses were styled in a pageant hairdo while her makeup mimicked that of her late mother's with a strong winged eye. 

Larry looked sharp in a powder blue suit, accessorized with a yellow tie and pocket square. 

He completed his look with a yellow flower pin that matched Dannielynn's gown on his lapel.