How To Dress For the Kentucky Derby: Your 60 Second Visual Guide

by Brett & Kate McKay on May 3, 2012 · 25 Comments

in Dress & Grooming, Style, Visual Guides

Madras Sport Coat. Straw trilby hat. Bow tie. Khakis. Madras sport coat.  Derby Casual for the Younger Man. Sport coat. Polo shirt. Pocket square. Khakis. Boat shoes.  The Go-To: Sport Coat and Trousers. Navy sport coat. At the derby, accessories make the outfit, so wear a splashy tie and pocket square. Saddle shoes. Light-colored trousers. Light-colored dress shirt.  Seersucker suit. Straw hat (Boater, Panama, Milan). Bow tie. Breathable fabric keeps you cool. White or light tan bucks or brogues, or go with a brown/white spectator for extra panache.

This post is brought to you by Life Khaki from Haggar What’s this?

Illustration by Ted Slampyak

Have any other Kentucky Derby style tips? Share them with us in the comments!

{ 25 comments… read them below or add one }

1 Jeremy May 3, 2012 at 10:21 am

Also applicable if you happen to find yourself in the unfortunate position of attending an Ole Miss football game.

2 Mike Dwyer May 3, 2012 at 10:56 am

I will rocking the ‘go-to’ look tomorow at the Kentucky Oaks. My only concern is the heat. It’s going to be a warm one.

3 Kenny May 3, 2012 at 10:58 am

I think an illustrated dress code for the Kentucky Derby INFIELD would be just as fun.

4 Bob Hiller May 3, 2012 at 12:25 pm

If you’re on horseback talking to someone and they’re on the ground, dismount. It ain’t polite to talk down to people. (from “Cowboy Etiquette” by Texas Bix Bender)

5 Collin May 3, 2012 at 12:26 pm

As a younger man in his mid 20s, I must say, being young doesn’t give you the right to dress casually to an event. Grow the $%^& up, and at least wear a button down with your sport coat. Polo shirts are for summer cookouts in your back yard.

6 Charles May 3, 2012 at 12:29 pm

@Bob… In other words, “Get off your high horse”.

7 Robert May 3, 2012 at 12:32 pm

I must agree wholeheartedly with Collin. Not to mention that wearing a sport coat (open, no less) over a polo just seems like a terrible clash of dress and casual.

8 Dustin B May 3, 2012 at 12:48 pm

Where’s the illustration for the shorts, t-shirt and flip-flops option?

I kid, of course.

9 Chris May 3, 2012 at 1:18 pm

It’s funny, I’m 19 and going to my first Derby this weekend myself. I was just googling yesterday about what to wear and went to the official Kentucky Derby website. They show a pic just like the “younger man casual,” and that’s what I decided to go with. So straight from the horse’s mouth! I think it’s a nice look for someone my age. Not too stuffy. Too many people on this site think you have to look like a nerd even when you’re young.
It’s the second pic in the slideshow.

10 Andrew May 3, 2012 at 1:37 pm

I used to think really rich people got dressed up to go to the track. Then I actually went to the track…

Let’s just say it’s about as far removed from high society as you can get.

11 Matt May 3, 2012 at 2:40 pm


If at an Ole Miss football game, I believe decorum dictates a flask of bourbon smuggled into the game, yes? Bourbon or other similar numbing agent. Oh, and bring double when playing Texas A&M. Those guys are insufferable. Thanks for taking them off the Big XII’s hands. No give-backs.

12 Cam from Indianapolis May 3, 2012 at 2:53 pm

Dressing for the Indianapolis 500:

1. Flip flops

2. Cut-off jean shorts with holes

3. Tank top with a generic American flag or bald eagle design (although wearing a shirt is optional).

13 David May 3, 2012 at 5:54 pm

@Chris: Not downing the casual look, but what do you mean by “people… think you have to look like a nerd even when you’re young?” Young men dressing like we have money and 9-to-5s whether we do or not isn’t nerdy; it’s swag.

14 Matt May 4, 2012 at 12:21 am

Modern polos and sportcoats do not look good together.

15 Collin May 4, 2012 at 10:20 am

Chris, that picture also shows a kid with his collar popped. One of the most important rules in learning how to dress is to ignore fashion advice from someone who pops their collar.

The fact that you refer to looking employable as dressing like a nerd shows that you have a long way to go.

16 Lewis May 4, 2012 at 10:26 am

Collin, Robert, and David sound like total P@ssies

17 Steven May 4, 2012 at 7:36 pm

Robert, I have to say I disagree with you last point. Sport coats are perfectly appropriate to with a polo shirt IF: 1) the sport coat in question is of a light material, not tweed or wool and 2) that it is an event like a garden party or outdoor brunch. I do think it should be closed by the middle button (3 button) or top (2 button) just to give it shape as it won’t have much (because it is light weight). If styled properly it can look very nice. However I do agree that it is not the look for the derby.

My usual “go-to” to look (for summer) consists of light colored, flat front trousers, white Oxford, and black and white herringbone sport coat (cotton but impeccable), and a bow tie. I’m 19 so I think that would work for “younger man casual”.

18 Justin McAfee May 4, 2012 at 10:29 pm

Why isn’t this called, “How to dress every day of summer!”

19 Pavegs May 5, 2012 at 1:58 am

It’s too bad the Kentucky Derby doesn’t follow the tradition of the Royal Ascot, where the gentlemen sport morning dress, which is probably the classiest style possible.

20 Greg K. May 7, 2012 at 3:18 pm

Or linen suit, white shirt, blue gingham check tie with bar, white cotton pocket square, and loafers, no belt.

21 Joseph May 9, 2012 at 8:41 pm

are these outfits interchangeable? could you wear a straw hat with a madras/navy sport coat instead? or spectators with afore mentioned coats? could you wear a regular tie with madras?

22 Royal May 10, 2012 at 5:45 pm

As a young man, I would definitely wear a button down instead of a polo for the younger look.

23 Ed May 15, 2012 at 11:24 am

@Pavegs Sadly, the typical American has NO clue what morning dress is. Then again Americans wear evening dress (“tuxedos”) for afternoon weddings.

24 Randy June 1, 2012 at 10:06 pm

The seersucker (any color) or natural white cotton-linen blend suit would be my choice. I have a two-piece seersucker in the most common blue-on-white stripe and a C-crown fedora-shape panama hat with the two-tone brown wing tip with ivory mesh ventilator shoes. I depart, however, with the tie. Some guys are iconoclastic and even courageous enough enough to wear a bow tie and I sort of like and admire that — in others. Even though I’m slender and have the requisite slender face, I don’t do bow ties. I wear one of my wide (over 3 1/2 inches wide) neckties and a pocket square with the seersucker.

25 Marge Von February 5, 2013 at 9:25 pm

I’d love to get a copy of this print. I’ve thrown a large party for almost ten years and I’d love to have this a part of my decor.

Let me know

Leave a Comment

Previous post:

Next post:

Site Meter