Here’s How to Dress For the Kentucky Derby

It’s time to do it right at Churchill Downs.


(Photo: Vineyard Vines)

The “most exciting two minutes of sports” is right around the corner, and with this yearly Louisville event comes one of best the parties of the year, complete with good bourbon, big stakes, and hats so large you could fit a family of four underneath. 

While million-dollar earning patrons visit the annual horse race to throw big money at champion stallions, the Kentucky Derby is an occasion rich in tradition that brings together regular folk, who frankly, don’t know shit about horses and are simply trying to have a damn good time.

Now, even if you’re planning on being belligerent (and please, don’t), you still have to look the part. While women pride themselves on the fanciest dresses with complimentary accessories, the Derby is a golden opportunity for guys to channel their inner Southern gentleman with a classy yet colorful style. The sartorial Derby mandate is to stand out, no matter what, so why not substitute a nice blazer and bowtie combo for your dreams of debauchery?

Vineyard Vines CEOs and co-founders Shep and Ian Murray pride themselves on crafting an effortless yet classic style that’s on display at the annual race. With the hope of every day feeling as good as the Kentucky Derby, here are some tips of the trade courtesy of the Murrays (with a little help from footwear brand Florsheim) that’ll put you at the top of that best dressed list you didn’t even know existed.

(Photo: Getty Images)

1. Embrace the event: “The Kentucky Derby is an American institution and one that truly combines sporting and style,” says Shep Murray. For someone who may not be as daring as his group of buddies, “pastel blue airs on the side of conservative.” It’s also never a bad call just to “add color in smaller doses with a fun tie or pocket square.” Your color palette should ultimately be limitless, but nothing screams derby like some playful pastels.

2. Anything could happen: Expect the unexpected during your visit to the Bluegrass state. “Be prepared for any weather scenario,” says Ian Murray. “Unfortunately, it’s not always sunny and warm. If you’re planning on eating dinner in Louisville that weekend you’ll wait just about anywhere, so grab reservations early.”

That doesn’t just go for the weather. Murray recommends you brace yourself for unexpected debauchery. “Pace yourself,” he says. “It’s a long day!”

3. Beat the heat: If the day shifts to an overwhelming swelter, you don’t want to start schvitzing like a fat kit at summer camp . According to the Murrays, it’s best to avoid early on-set heat stroke by going for removable layers and swapping out your regular cotton dress shirt for one of VV’s “performance” varieties. “They boast features like cool-wearing fabric, moisture management and quick-dry,” says Ian.

4. Go bold or go home: The Derby isn’t exactly the ideal home for a minimalist, so in order for you to stand up to that gorgeous woman across Millionaire’s Row, you’ll need something both polished but vibrant enough to have her unable to look away. When in doubt, go with a distinctive blazer. “Something in a fun fabric or color,” says Shep, “like our rose-print version this season is awesome and definitely an attention grabber. “

5. Don’t forget your fancy footwork: The challenge of stomping around all day is finding the perfect footwear that’ll pop without having to walk around in a pool of your own blood. If you’re aiming to go in the timeless route, Florsheim recommends a saddle tan Castellano Wing Ox: “The saddle tan colorway is anything but boring, and the classic styling will serve you well after the Derby when you’re back in the boardroom or out on the weekends.”

For those dressing from the bottom-up, start off your outfit with “a pair of Sabato Penny’s in eye-catching brushed leather colorways like teal, navy or red, which are the perfect choice to help you stand out in a crowd,” according to the company.

Good luck, and have a delightful (and stylish) Derby Day.