Dressing for the Kentucky Derby

by Antonio on April 28, 2009 · 19 comments

in Dress & Grooming, Style



This article is co-written by guest writer, The Houndstooth Kid, and our Style regular Antonio Centeno.  If you enjoy it, please visit the Houndtooth Kid’s blog for information and musings on vintage menswear.

Southern Style

On May 2nd 2009, the Kentucky Derby will be 135 years young; since 1875 it has been held at Churchill Downs in Louisville, Kentucky and has grown from a local event to one that is watched worldwide by millions. Inspired by the British Epsom Derby, the American version grew from the imagination of Meriwether Lewis Clark, Jr. and his efforts to cement Kentucky as one of the horse racing capitals of the world.  In this he succeeded.

The Kentucky Derby is a southern spectacle rich in tradition; Burgoo, Mint Julep, and the infamous Infield are all terms a first time attendee will become intimately familiar with. Two events in one, the Derby is both a race and a two week party where fashion takes center stage.  The 140,000 attendees in the stands and box seats are requested to dress “smart casual” on race day; in response, thousands dress to the nines in their best summer garb, modeling everything from the traditional to the, well, unique. A sporting event and fashion parade in one, the Kentucky Derby lets viewers take part in forging the summer’s fashions.

So what should you wear to the Kentucky Derby?  How do you dress for the parties and celebrations that surround this unique American event? A relevant question, because even for a man who is not attending the Derby or a Derby party, the classic styles that work at Churchill Downs can be utilized in any American city during the summer.


Image by jagwoodlex

The Derby and the Setting of Style Trends

The future of style is definitely worthy to pursue, but what of the past? My specialty is clothing of the 1930s and 1940s, the Golden Era of American Style when the United States and its ambassadors of style set the tone that the world followed.  In this spirit of tradition, we’ll be building a classic summer outfit for the Kentucky Derby while looking through the lens of the Golden Era for inspiration. While we could take a look at summer suit styles (such as the classic seersucker) or the stroller (the daytime equivalent of the dinner jacket), we’ll instead look at an outfit most men already have the basic ingredients to build: the sports coat and odd trousers combination.

Starting at the Top – The Derby Hat


Perhaps the best reason to attend the Derby is to wear and look at the wide range and abundance of headwear.  With umbrellas banned and at the mercy of the weather, most attendees quickly realize the usefulness of a good hat. While women tend to have the most fun when it comes to headwear fashion, the men aren’t exactly slackers and will be sporting many classic styles. Straw hats have been favorites of the past since its lightweight build and weaves keeps the sun off the wearer’s head while allowing air to flow freely. Boaters, Panamas, Milans and other semi-formal straws are all solid choices for the discriminating man.  If straw is not to your taste or rain is threatening, turn then to the trusty felt hat such as a fedora or homburg.  If made from a lightweight felt, it will see you through the heat and glare in style.

Click here to get a primer on different hats, and here to find the best hat for your face shape.


Image bycphovers

Of course if none of the normal hat choices fit you, you can mock up something all your own.

Under It All – the Derby Shirt

A great Derby shirt acts as a foundation for the outfit; it should be made of a breathable fabric such as cotton and woven with a tight enough weave to prevent heavy wrinkling.  Like a blank canvas, it allows the wearer to paint upon it with smooth strokes as he matches a jacket, trousers, pocket square, and tie to create his look.  Shirt style and fit should depend upon personal preference and build, but the color should in my opinion be somewhat muted – the Kentucky Derby is a day in which a man’s accessories make the outfit, so an attention grabbing shirt should be avoided so as not to overwhelm them. The plain white shirt, especially for a warm weather event like the Derby, provides a clean and unassuming background.  It allows other components of a man’s outfit such as a tie or pocket square to shine more brightly.

Hike ‘em Up! – The Derby Trousers

Although you could wear a suit to the Kentucky Derby, I’m a bigger fan of a more casual but just as stylish look that requires more thought to pull off: the matching of a sports jacket with a pair of odd trousers.  Khaki and light grey are the most common color for summer odd trousers, however they are not the only options.  The nature of the Derby encourages some experimentation, and the man willing to wear cream or white trousers to contrast with his jacket will really stand out.  Smart combinations like a blue jacket with cream trousers create a striking image and can make the wearer appear deliberate and confident with his choices.  While toothpick-legged, low slung pants are in fashion at the moment, the high-waisted and wide, straight-legged trousers of old are never out of style. Pleats and cuffs or lack thereof is up to personal preference, but keep in mind that cuffs add weight to the leg and help it drape better. A full drape makes for elegant trousers.

The Main Event – The Derby Coat


Image by bill.streeter

The most observed layer of clothing a man wears to the Derby is his sports coat.  Literally a jacket for sporting, the modern sports coat can be traced back to the early 20th century when such manly hobbies as angling, hunting, target shooting and equestrian sports required rugged clothing that still had to retain a gentlemanly feel.  Demanding a large range of motion in the upper body, the sports coats of old afforded such movement by being built with belted, bi-swing, pleated, and center gusseted backs.  Today when choosing a Derby sports coat, look for an unbridled yet sophisticated style. I often see this combination in vintage sports coats, as that they are not too far removed from their wilderness roots.  Promising signs are patch or hacking pockets, interesting fabric patterns that seem too busy for a suit, and any of the back treatments mentioned above.  As to color, sports coats come in a wide range of them; navy blue, brown, tan, green, cream and even white are great for both late spring and summer.  All will be on display at the Derby, with perhaps the white and cream being the rarest.  Not because they are inappropriate, rather only because of their difficultly in keeping clean.  However the man that can wear white is guaranteed to create a striking figure.

Walk a Mile – Derby Shoes


Since you’ll be on your feet quite a bit at the Derby, it is imperative to find comfortable footwear that will fit right in at the event. Any semi-formal shoe will work as long as it accentuates the rest of the outfit. However, this being a summer event, you might try something a little more daring such as the saddle shoe or even the classic spectator. A brown and white spectator shoe will go with most any outfit and adds some color and visual interest that would otherwise be missing. Even a brown or white suede oxford can stand out well among the crowd while keeping with the tradition of the event.  If you’re a man after the full Derby experience, a pair of equestrian boots like those of old might trip your trigger.

Dressing for the Infield?

If you are headed to the drunken party known as the Infield, well, you can ignore everything in this article except this bit of advice:  Eat a solid (not liquid) breakfast, wear sunblock, drink some water, and for goodness sake, avoid the cameras.


Dress well when you attend the Kentucky Derby, for a true gentleman understands the history of the event and realizes it’s one of the few remaining bastions of genteelness in America.  Add to the enjoyment of those around you by dressing in the mood of the festivities; like a uniform, it’ll help you better feel the ambiance and create lasting memories. If can’t attend the Derby in person but are looking for an excuse to get dressed up in Southern style, why not throw a Derby party at your house this weekend?

Written by The Houndstooth Kid and A Tailored Suit’s Antonio Centeno

A hat tip to Andrew Holtzclaw for requesting this article

{ 18 comments… read them below or add one }

1 Cowboy Bob April 28, 2009 at 5:59 pm

Although there are some slight similarities between the south and the west, I’d rather do the cowboy thing. The affectation is quite fun.

2 Jacoba April 29, 2009 at 3:16 am

I’m a straight woman and actually subscribe to your online mag – at first because of the whisky article which I considered to be excellent, so much so that I put you on my site as a favourite read, but lately I have found the articles to be very insightful, well written and thoroughly enjoyable.

Thanks for teaching me to understand how the other half ticks – and thank God you aren’t all as shallow as I thought! ;)

3 JC April 29, 2009 at 6:57 am

You forgot the classic – seersucker.

4 Rob April 29, 2009 at 3:55 pm

Yet another article that fetishizes the past instead of promoting individuality and independence, virtues that men *should* live up to. Dressing up like it’s the ’40s is just as silly as emo kids dressing up like vampires or hipsters dressing up like lumberjacks.

5 Jones April 29, 2009 at 5:15 pm

I suppose you’ve never been to the Kentucky Derby, but this is actually how people dress at the present day derby-in hats, trousers, and sports coats. It’s not fetishizing the past to dress as the tradition of the event dictates. You could show up in jeans and a t-shirt to watch, but that’s not being an individual, that’s just being a jackass.

6 Cowboy Bob April 29, 2009 at 6:13 pm

I tend to agree with Rob, that it’s silly to dress in that particular fashion for that event. Jones is being heavy handed because Rob did not say anything about jeans and a t-shirt, and Rob seems to support suspending individuality, and even caving in “as the tradition of the event dictates”. That means, to me, that if I’m not going to dress in that particular style, I either cannot attend or I’m a jackass if I do something different.

7 Jones April 29, 2009 at 6:58 pm


The fact that you would view dressing for an event as tradition dictates as “caving in” says a lot about the disrespect men have for others in this day and age. If a wedding is a black tie affair, you dress in black tie. If the event is a cowboy square dance, you don’t dress in black tie, do you? So if the event calls for old fashioned southern style, you dress in old fashioned southern style. These days, individuality has come to mean doing your own thing and not caring about others. A gentleman can be his own person, while respecting others at the same time. By dressing in a certain way for an event, you help contribute to the ambiance and experience shared by everyone.

8 cyber5 April 30, 2009 at 12:26 am

Since I have never attended the derby in person and usually watch it from the track in Phoenix or a casino in Vegas, I tend to break these rules. However, I do respect the Derby and the sport of horse racing itself. On a typical raceday I’ll wear any one of my Race related Tees and jeans – but on Derby day I usually opt for a trouser sportcoat look. This year will probably be khaki trousers and a white sport coat.

I think Bob and Rob up there need to understand this is 135 years of tradition, not conformity.

I have always asked my girl to come along to experience the thrilling 2 minutes that is the Derby – provided she wears a hat. For the last few years, I have invited my friends to join me at a table in the clubhouse – once again, Hat IS Required for all females.

During the day my cohorts can order any damned thing they like to drink – but EVERYONE drinks at least one julep first. Bourbon and mint…mmmm….what else do u want outta life – besides hitting the tri to pay for the day at the track?

9 Justin Luddington April 30, 2009 at 12:40 am

Well said, Jones. How you dress should have more to do with the respect you show others than yourself.

10 Horatio April 30, 2009 at 10:22 pm

Cowboy Bob said,

“It’s all about me me me!”

I might have paraphrased a little.

Other commenters have said, in their own ways, what the fine movie “Blast from the Past” pointed out: “good manners are just a way of showing other people we have respect for them.” That movie is also the source of something else we should always bear in mind: the “short and simple definition of a lady or a gentleman is, someone who always tries to make sure the people around him or her are as comfortable as possible.”

See, Cowboy Bob, by dressing appropriately for a situation, we are showing respect for them and their traditions. By dressing appropriately, we are making other comfortable. I don’t pretend to be something I’m not, and so I don’t wear cowboy boots and cowboy hats. However, if I were to go to an event where that was the appropriate garb, then I would either refrain from going or respect that tradition and dress that way. It’s only showing others the kind of consideration they deserve, and the kind of consideration I would like them to show me.

11 Horatio April 30, 2009 at 10:24 pm

By the way, who makes those wonderful spectators featured in this article?

12 Cowboy Bob May 2, 2009 at 4:30 pm

Sorry, Jones, I do not equate a horse race with a wedding. If the wedding is a standard, traditional affair, I’m going to follow along. But some weddings show the individuality of the bride and groom, and I may have to dress in a manner that I consider inappropriate to the solemnity of the occasion.

But you want me to “help contribute to the ambiance and experience shared by everyone”. It’s a friggin’ horse race, for crying out loud! I’m not going to buy a set of clothing for two minutes of racing, plus gambling and boozing before and after.

“These days, individuality has come to mean doing your own thing and not caring about others.” Those kinds of “individuals” are irresponsible, immature school kids. Or at least have that mentality. True, manly individuality shows respect for people and the occasions that deserve it.

13 utbna98 May 4, 2009 at 3:10 pm

I guess you can wear whatever you want in some places at the track. But one reason some people wear a sport coat and slacks is that the doorman won’t let you in if you are wearing anything else. So, wear jeans and a t shirt and show your individuality, but you won’t do it upstairs.

14 Ryan May 24, 2009 at 8:01 pm

Horatio, I second that, anyone know who makes those shoes?

15 Mike at The Big Stick July 21, 2009 at 9:50 am

Unfortunately i missed this post back in April, but I can’t resist commenting now…

I’ve lived in Louisville for all of my 34 years and I’ve attended the Derby probably a dozen times. Here’s my two cents:

I agree that if you are doing the Infield then you should just dress comfortably, wear sunscreen and try to not drink yourself into the hospital.

For the grandstands there is no ‘required dress’ but the local logic is that the closer you are to the center of the grandstands, the nicer you should dress. Derby tickets aren’t cheap and it seems pretty silly to pay all that money and not get the full experience. And the dress is part of the experience. We have seats every year on the far end of the grandstands. In that section it’s a mixed bag. I see people in shorts and polos and people in three-piece suits. As you get closer to the center where all the owners are, most men wear a suit or a blazer and tie.

As a Southern man I prefer the blazer and contrasting pants to a suit most of the time. One thing about Derby is that ‘loud’ or extremely colorful blazers are encouraged. I have one searsucker and one madras plaid blazer that I rotate for the Derby and that’s pretty much the only thing I wear them to (the searsucker is appropriate for church in the spring). Also, loud ties are a regular sight, usually with a horse/racing theme. Hats are becoming more common among the men. Mostly straw fedoras that aren’t too hot (the weather for Derby can range from the 40′s to high 80′s depending on the year).

All of the comments about being unique, etc are pretty silly IMO. For the Kentucky Derby the dress is a big part of the experience. Stand there in a good outfit, sing My Old Kentucky Home with 200,000 other people and tell me it’s not a moving experience. We’ve had friends in town for the Derby many times and they all say they are glad they went for the more formal attire. It’s sort of like if I ran with bulls in Spain I would wear the typical garb for that. You’ve got 364 other days to be ‘unique’. But respecting tradition is about being a part of something…not deliberately ignoring it.

16 Chris October 6, 2009 at 2:59 am

Wow. The lack of respect for tradition. I know it’s an American thing, to reinvent the wheel every generation, but not respecting something that is valued by many others just to “express your individuality” is just plain rude. But then again recognizing when one is rude requires that one has manners in the first place. Manners dictates you dress appropriately for the event you are attending. Thank God for my Grandmother who refused to believe good manners should be relegated to history…like these gentlemen think should happen with Derby tradition. I would love to attend the Kentucky Derby someday and dress up for it. Saying it’s just a horse race belittles the long history and tradition that go with it. The Queen of England attended the races a few years back. That’s the thing. We wanted this derby to rival the big ones in England, Australia, etc. Well those races have a dress code too and it sure ain’t jeans and a t-shirt. Tradition is not something that need be stifling, but you can express your individuality within its bounds quite easily. It’s just plain rude and lazy to refuse to do so.

17 Sam June 25, 2010 at 7:18 pm

You know why jeans and a T-shirt are called street clothes? Because you wear them on the frickin’ street and not the Kentucky Derby. I don’t understand how you would not just be embarrassed to death to be the only person there who was being a “unique” idiot.

18 Clint May 3, 2013 at 9:21 am

The thing is that it is a lot less like dressing up for a Renaissance Festival and more like just wearing nice, semi-formal clothes. We live in a world where instant gratification and being a perpetual teenager is the acceptable lifestyle for men. What’s wrong with wearing clothes that are more formal than what your boss expects you to wear to work? After Prom or our Weddings, unless you count funerals, there is no reason anymore for men to put on the dog. So, sure go nuts at this, and if you don’t want to dress like it’s the 1940′s go ahead and refrain, but once you realize YOU are the anachronism, you can tell yourself how cool you were while you drive home alone.

Leave a Comment

Previous post:

Next post:

Site Meter