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Style Scenario: Kentucky Derby 2021

April 27, 2021 By DeJuan M. | Heads up: Buying via our links results in us getting a commission (not always, but just about), which helps keep the lights on around here. We also take your privacy rights seriously. Head here to learn more.

About the author: DeJuan is a husband, father of a 10-year old son and 3-year old daughter, and a chemical engineer. He enjoys watching sports, reading, playing and listening to music, and of course men’s style. He lives in Cincinnati, Ohio and works from home in inside sales for a chemical process equipment supplier.

What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. That’s what these are for. As a former resident of the Commonwealth of Kentucky, I especially appreciate the first Saturday in May. The Kentucky Derby. The Run for the Roses. Even if you don’t go to the track, or are still keeping yourself isolated and/or distanced due to COVID, it is still a great excuse to get dressed up and watch the day’s festivities. Here is a bit of inspiration to stylishly enjoy the greatest two minutes in sports.

Kentucky Derby Style Scenario 2021

The Suit: J. Crew Factory Slim Unstructured Thompson Seersucker Suit Jacket and Trouser – $154.70 w/ LOVE . The Kentucky Derby is a great time to bring out seersucker. It is a stylish, festive option for the spring and summer, and is a classic in the South. If you aren’t feeling a full suit in seersucker, try a simple pair of blue trousers with a blue/white seersucker jacket instead.

The Pocket Square: Harrison Blake Apparel Heritage Paisley Pocket Square – $20.00. A nice pop of color in the pocket without being too loud or obnoxious. The paisley pattern makes for a nice contrast in patterns with the stripes on the jacket.

The Shirt: Spier & Mackay White Oxford – $49.00. Or, whatever your favorite and best fitting white dress shirt happens to be. Button-down collar brings the formality down a touch for a smart casual feel.

The Hat: Goorin Bros. Albuquerque Straw Hat – $60.00. The Kentucky Derby is known for the ladies’ hats. Gentlemen can participate too! Especially useful if you attend an outdoor event on a sunny day.

The Sunglasses: J. Crew Dock Sunglasses – $52.12 w/ COUNTDOWN ($69.50). Just in case you are attending or hosting an outdoor derby party. With a keyhole bridge and retro styling, these sunglasses will look right at home with seersucker. Available in 3 different color schemes.

The Belt: Gap Leather Belt in Cognac – $21.57 w/ TREAT and PERK ($39.95). Old reliable once again, but this time around give the cognac color a go, as a nod to the libations that are common to Derby day. You could also look for a suede belt to coordinate with the color of the suede shoes, but if not you’ll be fine with this belt.

The Shoes: Allen Edmonds Dylan Suede Penny Loafer – $221.25 ($295.00). Suede penny loafers to finish off a laid back, yet polished and put together look. Any of the three available colors would work well with a blue/white seersucker suit, but Bone feels like a classic choice for a warm-weather southern look.

The No-Shows: Bombas Men’s Lightweight Merino Wool No Show Socks – $15.00. No-show socks for a sockless look while actually wearing socks. Soft, moisture wicking, breathable merino wool.

The Watch: MVMT The 40 – Rose Gold Natural Tan – $102 ($120). The watch I wear almost every day. Simple, minimalist white dial. Rose gold casing is unique without being too bold.

The Drinking Glass: Kentucky Derby 147 12oz. Mint Julep Glass – $6.99. Bit of fun here. Includes the name of every previous winning horse printed on the side, which could come in handy someday on a trivia night.

The 2021 Kentucky Derby is Saturday, May 1st. Top Photo: J. Poe

Filed Under: Accessories, Clothing, Drink, Shoes, Watches Tagged With: style scenario, what to wear to a kentucky derby party, what to wear to a kentucky derby party for men

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