How to Dress for the Derby: A Style Guide for Men

They call it the most exciting two minutes in sports, however the Kentucky Derby is about far more than just a two-minute horse race — It’s about being seen! Whether you are on Millionaire’s Row rubbing elbows with some of the biggest celebrities in the world, or at a tailgate with some of your best buds, you better come looking fresh-to-death.

We’ll tell you exactly what the well-dressed man will be wearing at the track and how to add the right amount of modern style to some southern tradition, and if you find yourself looking to make a bet on one of the ponies take a look at DG’s guide to horse wagering.


how to dress for the derby seersucker

Seersucker Suit

Probably the most iconic (and cliché) suit for any southern gentlemen is the seersucker suit. Loads of gents will be wearing seersucker, but there is a way to do it and a way to do it with finesse. Ditch the baggy suit your father finds stylish and find a good tailor to size you up for the perfect fit. Even if you just picked up a suit from a local retailer, there are likely some areas that could be taken in a bit that will transform your look from good, to grrreat! Make sure you have a solid white dress shirt (no pastels or other colors) to match and find a bow tie (yes, that’s right) a BOW TIE that is solid in color (navy, dark green, dark red) to bring your outfit together.  If you need help learning how to tie your fancy new wardrobe acquisition, check out our DG bow-tying guide.  Finally, I would suggest wearing suspenders, preferably brown leather, underneath your jacket. Not only would it look great with your complete outfit if you had to take your jacket off, but it’s also more comfortable. While the seersucker suit may be a little played out, it’s by far your safest style bet at the races!

If you want to escape the seersucker look go for a lighter, powder blue or camel colored khaki suit and apply the same rules as above.

how to dress for the derby double breasted

Mix & Match

An alternative to the traditional suit is mixing and matching your pants with a jacket. When done properly this look makes a bold, impressive statement. Pants are an eye-catcher at a distance, but leave the sun-drenched pants at home. Turn your attention to some floral/paisley patterns that are two-toned, or to some heather grey plaids that are lightweight. Combine a slim fit, navy, double-breasted jacket with a solid white dress shirt that is slightly unbuttoned for a cool and sophisticated look that the guys will envy and the ladies will adore!


how to dress for the derby men

Relaxed & Sophisticated

The weather in May can be quit unpredictable and there is nothing worse than sweating through a suit on a hot and muggy day. That’s why this final look is perfect for the guy that doesn’t want to suffocate in the heat, but still has a lot of swagger and class. Find yourself a solid colored waistcoat coupled with a bow tie and newsboy styled cap for a very respectable, yet relaxed look.

Derby Do’s

  • Find a pair of sunglasses that will be as timeless as your look. Oliver Peoples has some great styles for men and one can never go wrong with the oh-so-classic, Ray Ban Wayfarers.  Tortoise shell is highly recommended & a sign of a true DG.
  • A great lapel accessory that “pops” is an absolute essential. Whether it’s a vintage pin, seasonal flower, or even the handiwork of a skilled taxidermist, find one that stands out but doesn’t compete with your tie or pocket square.
  • If you prefer to opt for more traditional neckwear- add some texture to your look with a knitted tie, or utilize some springtime flare with an interesting floral pattern.
  • Shoes: Penny Loafers, Bucks, Wing-Tipped and for the most dashing… Slippers!
  • If you’re going to wear a hat (as many men do) make sure it’s lightweight & fits properly.  Straw boaters or fedoras are popular, and newsboy caps are always a solid & stylish alternative.
  • Carry a flask!  And fill it with some fine Kentucky Bourbon, too.  You wouldn’t be a DG if you didn’t!

Derby Don’ts

  • Leave the needlepoint belt at home. You’re a grown-up now and the BEST dressed man at the track doesn’t have time for needlepoint belts.
  • Croakies. No, just no! If you’re not responsible enough to take care of your sunglasses then maybe you shouldn’t wear them in the first place.
  • White accessories: Toss them in the Ohio River! This includes, but is not limited to, loafers, watches, belts, ties, sunglasses, etc!
  • I don’t’ care what the “experts” say, ditch vibrant colors like Key Lime, Ocean & Citron. Nobody has ever made this “look” a good one – ever!


Arguably, The Kentucky Derby is THE highlight for the state of Kentucky each year. Louisville is placed under a microscope by bloggers, reporters and all other forms of media for the rest of the world to catch a glimpse into the Kentucky lifestyle. Dress to impress ya’ll!

More from Kerry Glass

How to Dress for the Derby: A Style Guide for Men

They call it the most exciting two minutes in sports, however the...
Read More

Leave a Reply

Your email address will not be published. Required fields are marked *