The first weekend in May annually hosts what many call “The most exciting two minutes in sports.” Other than watching Greg Maddux run out a very rare triple hit by a pitcher back in the ’90s, I have never heard anything in sports carry that same label. Ever since the grandson of the Clark half of the Lewis and Clark expedition traveled to Europe and gained a love for the sport of horseracing, the Kentucky Derby has captured the hearts and minds of race fans everywhere.
But, you know I don’t write about horse racing. I write about men’s style. This brings us to the best part of the day at Churchill Downs: Kentucky Derby outfits. My favorite part of the event is seeing how creative men can get with their looks. The bright colors, the hats, the ties, the fabrics. Maybe it is me being a menswear nerd, or perhaps it is just as sartorially interesting as the Oscars. Either way, I wanted to get some help on how to dress for race day, so I reached out to Michelle Kohanzo, Head of Brand for Tie Bar, and she gave me some insight on how you can capture all the attention without looking like a try-hard.
It all starts with the mindset
Is it all just wearing the brightest colors you can find? Loud hats, patterned pants, and a light sport coat and bow tie? I mean, if it were that simple, then anyone could do it without any kind of guidance. But we have seen what happens when some men dress without guidance. So what is the mindset that you should be using when putting together one of the best Kentucky Derby outfits? Kohanzo thinks this is where you dig deep, find that quintessential Southern gentleman charm, and bring it out.
I think the proper mindset for the Derby is southern gentlemen at a summer soiree. Think linen, crisp cotton, and loads of floral. The Derby is absolutely an event where you can go all out with color, but sophistication is key — think a beautiful natural suit, with bold accessories.
It is about colors, but what about the styling?
If you think about the things we dress for specifically — holidays, events, and seasons — colors play a big part in the process of putting together a great look. That means it is more than probable, even likely, that we will over-focus on bringing the kind of pastels and what they call “Derby Colors” into our outfits and overlook something even more critical: styling. So how do you balance the two and put together a well-thought-out and stylish Kentucky Derby look?
It’s definitely all in the styling, start with your suit and or bottoms and build from there. I love pulling in “Derby” colors like red, pink and green in your accessories.
Putting together the perfect Kentucky Derby outfits
As the day gets closer, you will want to start putting together the looks you want and making decisions. But what are the things you need to keep in mind, and how do you go about assembling the perfect ensemble? Michelle Kohanzo has three tips to get you started.
Impeccable tailoring, chic, playful accessories, and breathable fabrics — the last thing you want is to be overheating in the Louisville sun.
Starting with the fabrics, focus on natural fibers like linen and cotton. These are going to breathe better than synthetics. And if you have never been to a Southern gentleman’s spring or summer, you may not understand until it’s too late. They can get brutally hot and unbearably humid and sweaty, so much that it is noticeable, and that isn’t a good look. Now that you have the fabric figured out, definitely make an appointment with a tailor and ensure everything fits perfectly. I know we talk about it a lot, but fit is the number one factor in a great look. Finally, make sure you have the right watch, a stylish pocket square, an ascot if you elect to be more playful than the tie, and finally, don’t forget a great brimmed hat to top the whole thing off.
Stick to these tips, and you may find the people around you are missing the most exciting two minutes in sports because they are admiring your look. Now go place a bet. When you look good, you feel good, and when you feel good, you can’t lose. Once you win the big wager, you can go shopping for next year’s winning look.
