Kentucky Derby fashion is important to men as well as women. (Photo by Eclipse Sportswire) 

For thousands of people, the Kentucky Derby is far and away the single greatest event, sporting or otherwise, they attend in a given year. When preparing for an event as significant as the Run for the Roses, often the hardest thing (even for the gents), is determining your outfit.

Probably plenty of tough guys out there reading right now are thinking, “Do you honestly think I care that much about fashion?” In reality, if you’re attending the Kentucky Derby, you should.

The Derby is one of the oldest, most passionately celebrated traditions in the history of American sport. It’s truly a magnificent scene, whether in the infield standing shoulder-to-shoulder amongst thousands of screaming degenerates, or in the clubhouse sitting with … well, thousands of screaming degenerates, you have to keep in mind that everything about Kentucky Derby day is a competition.

For the guys, you want to win the most money, be seen with the most beautiful young ladies, and quite frankly, look the best you can possibly look.

I’ll remind you that looking your absolute best isn’t easy in this environment, especially after several hours in the blazing sun accompanied by numerous cocktails, so you have to be ready for anything. And when it comes to your outfit, the main objective is to ensure you not only look good, but that you feel comfortable with yourself throughout the day.

LOOKING GOOD ISN'T YOUR ONLY PRIORITY

Photo by Eclipse Sportswire

A couple quick pointers to keep in mind…

Know the weather. Unless the forecast calls for a constant torrential downpour, sunscreen is never a bad idea. If you’re lucky enough to have a covered seat for the entire day, this doesn’t apply to you so much.

Determine beforehand whether or not you’ll be venturing to the infield. Look, if it’s your first Derby experience, it’s definitely worth checking out. Pro tip: no matter how sunny it is on a given Derby Day, mud always is a possibility in the infield.

If there’s any chance of rain, bring a poncho. Another idea to establish a good covered spot to meet your friends in the event of rain. You could be spread out all over the place but when you know it’s time to get cover, it’s a good way to meet your individual Derby crew to regroup. A meeting spot also comes in handy when it’s time to leave.

If you know it’s going to be hot, Gold Bond is a man’s best friend. I won’t go into detail on this one; hopefully you guys can figure it out. The last thing you want to be on any Derby Day is a sweaty mess.

Pace yourself. This is probably the most important piece of advice I can provide. Remember that it’s a marathon, not a sprint and that no outfit can look that good when you’re eight mint juleps deep at 4 p.m. 

Dressing for the Kentucky Derby 

This photo from the Art of Manliness serves as a good base for how to form your Derby ensemble:

A major take away from this photo: none of these looks include shorts. Through my experience, multiple veterans of the game have repeated a saying: “horse racing is not a game meant for boys in short pants.” What I gather from that was that you have to have thick skin to be able to survive in this sport and if you wear short pants, you usually don’t have thick skin. Case in point: I don’t wear short pants to the Derby and neither should you.

Suits

One question you might ask after studying this photo is, “how do I know if I should wear a suit?” On Derby day, if you have any ticket that includes your very own personal seat, or any type of clubhouse admission, then a suit is appropriate. Obviously if you are in the Turf Club, The Mansion or the Jockey Club Suites, a suit goes without saying.

Side note: for those not lucky enough to have a seat in what I now can call the “suit section,” a tie also becomes optional. If you’re considering rocking the “Derby Casual for the Younger Man” look, check out this link from Dappered, titled “How to Wear a Polo With a Blazer.”

Photo courtesy mensstylepro.com

When it comes to wearing suits in Kentucky in May, think light. Cottons and linens are ideal for the heat. Seersucker is always a classic Derby look and khaki is very much in style right now. The last thing that comes to mind on Derby day is a dark pinstripe wool suit. Cottons and linens are also popular materials for ties now too.

Photo courtesy Dessy.com

Inspiration

Most of the looks I’m presenting are just ideas to provide inspiration on how to craft your own personal Derby Day look. Don’t forget the cliché saying, “It’s not what you wear, it’s how you wear it.”

I also want to remind you not to overdo it. Try and limit your color scheme to three colors if possible. You don’t need a tan suit with a pink shirt, green tie, blue pocket square, multi-colored belt, yellow socks and brown shoes - I repeat don’t overdo it. Brown goes with blue, tan/khaki goes with white and white goes with black. If you can limit it to one of those three two-color combos, you’ll be golden.

Below are the ten items of clothing/accessories to consider (in the order I’d typically put them on): 

1. Shirt

Gitman Bros. Shirt

When deciding on a shirt, one of the first things I consider is the fit. I prefer something more slimming for a more modern look. Whether you decide to rock the button-down or non-button-down collar, make sure it’s not too long and floppy. Also this may just be my personal preference, but if you are going to wear a collar without buttons, wear a tie with it. 

2. Socks 

Brooks Brothers Crew Socks 

Although they won’t be the most visible item in your Derby outfit, getting a little creative with your sock game can add that extra touch to get you noticed. I’ve noticed people doing this more today but I’m not a proponent of mixing black socks with brown shoes, or vice versa. Also, the only time I feel it appropriate to match your socks to your pants is when you’re wearing black. 

3. Pants 

Slacks from GAP

If you’re not going all out with the suit, then I recommend something lightweight and comfortable, usually flat-fronted like the khakis shown above from Gap. If you are rocking a suit, sometimes pleats aren’t a bad idea as they can provide a little extra breathing room where it counts. If you go with pleats, be sure to go single pleat, not double. And generally just make sure the pants don’t look too baggy or bulky on you.

 

4. Tie/Pocket Square 

Ties and Pocket Squares from The Tie Bar 

As I mentioned before, linen and cotton ties are trending, so if you’ve never tried those before I recommend it for this Derby season. If you live under a rock and haven’t heard of The Tie Bar yet, they have some great ties for deals I’ve never seen. Also for a little fun, check out Chipp Neckwear’s novelty tie selection. 

5. Belt

Left to right: Belt from Bluegrass Belts, Belt from Vineyard Vines

If you’re really trying to get into the Derby spirit, Bluegrass Belts has the classy looking “hoof pick” style buckle, and as the official sponsor of the Kentucky Derby, Vineyard Vines has offered up this signature multi-colored belt for the uber-preppy race fans out there. The obvious rule of thumb here is to match the leather color in the belt to your shoes.

6. Shoes 

Left to right: DSW Shoes, Aldo Shoes 

When it comes to kicks, I favor the more traditional styles above. The Aldo link takes you to a page with several different color options. Horse-bit loafers and traditional boat shoes are some other options to explore if you don’t go the suit route. Personally I wouldn’t go an entire day without socks, especially in new shoes, but some guys can pull it off. Don’t forget the Gold Bond if you plan on going sockless.

7. Jacket

Left to right: J. Crew Sport Coat, JCPenny Sport Coat, Uniqlo Jacket

The jackets above seem like they’d fit in better with a more casual look, but don’t be afraid to throw a tie on with one of these. I prefer a sport coat with thin lapels. I probably wouldn’t go as loud as the middle photo but there are people out there who want to stand out, which is perfectly fine. I could be in the minority on this, but it is my preference to tuck the flaps of the front pockets into the pocket. It allows for easier access into the pocket and I think it’s a slimming look.

8. Watch 

Revolveclothing.com Watches

The three watches above and several others can be found on revolveclothing.com. It’s safe to say that if you’re going to be wearing any leather (belt, tie, shoes), make those leathers match accordingly. You can try and match the colors on the Winston Print Series band to the colors on your tie, socks, belt, pocket square, or all of the above.

9. Shades

Revolveclothing.com Sunglasses

I also found these different pairs of shades I liked at revolveclothing.com. They have a great selection of some really unique styles. It is my position that going to any race track on any day without sunglasses is inexcusable. Besides combating the actual brightness of a sunny day, shades also come in handy to disguise the fact you might be a little tipsy or hung over.

10. Hat

Blake Collection from Christine A. Moore 

Personally, I’ve never been a huge fan of Derby hats for two reasons: my head is huge and I have phenomenal hair. But if you’re in the market for a hat, Christine Moore is the go-to designer for Derby hats. She actually designed a fedora for me when I was a Brand Ambassador for ABR. When she asked my hat size, she didn’t think I was serious when I said “eight.” Lo and behold she fitted me up; let’s just say it was a big hat.