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Mar 09, 2025
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How to Dress for Derby Day

2 years ago
1 min read

by Michael Satterfield – Lead Photo via Kentucky Derby – 04/27/2023

The Kentucky Derby is one of the signature events in the world of sports and is known for its glamorous atmosphere, elaborate hats, and stylish outfits. Men attending the Kentucky Derby or the countless Derby viewing parties held around the world are expected to dress to impress. Personally, I will be attending the Brazos Valley Symphony Orchestra Gala and Viewing Party which is the perfect excuse to get my seersucker suit and floral bowtie. If you are going to be heading out on May 6th here are five ways for men to dress for the Kentucky Derby.

Classic Suit and Tie

A classic suit and tie is a safe and stylish option for men attending the Kentucky Derby. Opt for a lightweight fabric such as linen or cotton to ensure comfort in the warmer weather. You can choose a classic suit in a neutral color such as navy or grey and pair it with a crisp white dress shirt and a solid-colored tie. Finish off the look with a pair of leather dress shoes and a matching belt, but add a pop of color with a tie or boutonnière, and be sure to have a great hat.

Preppy Casual

If you prefer a more relaxed look, you can opt for a preppy casual style. This involves wearing a pair of khaki or pastel-colored pants, a button-down shirt, and a lightweight blazer. This look is both stylish and comfortable and can be paired with loafers or boat shoes for a more casual vibe. A Panama hat with a colorful hatband is a nice way to add some flare. 

Southern Gentleman

For a more classic southern look, you can opt for a seersucker suit, my personal favorite. This lightweight fabric is perfect for the warmer weather and gives off a classic Southern vibe. Pair the suit with a white dress shirt and a patterned bowtie, and finish off the look with a pair of brown leather shoes and a straw boater hat.

Bold Statement

For those who want to make a bold statement, you can opt for a brightly colored blazer or sport coat. Pair it with a pair of pastel-colored pants, a white dress shirt, and a colorful tie. 

Casual Chic

For those who prefer a casual look, you can opt for a pair of well-fitted jeans, a casual button-down shirt, and a blazer. This look is both comfortable and stylish and can be paired with loafers or sneakers depending on the vibe you want to achieve.

In conclusion, the Kentucky Derby is a glamorous event where men are expected to dress sophisticated yet comfortable. Whether you opt for a classic suit and tie or a bold statement, the key is to choose an outfit that makes you feel confident and comfortable. By following these five ways to dress for the Kentucky Derby, you are sure to turn heads and make a statement at this prestigious event.

Michael Satterfield

Michael Satterfield, founder of The Gentleman Racer, is a storyteller, adventurer, and automotive expert whose work blends cars, travel, and culture. As a member of The Explorers Club, he brings a spirit of discovery to his work, whether uncovering forgotten racing history or embarking on global expeditions. His site has become a go-to destination for car enthusiasts and style aficionados, known for its compelling storytelling and unique perspective. A Texan with a passion for classic cars and motorsports, Michael is also a hands-on restorer, currently working on a 1960s SCCA-spec Formula Super Vee and other project cars. As the head of the Satterfield Group, he consults on branding and marketing for top automotive and lifestyle brands, bringing his deep industry knowledge to every project.

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