Attending the 2016 Kentucky Derby? What You Need to Know!

The Kentucky Derby is a unique event. It can’t be compared to baseball, football or even NASCAR — despite the fact that horse power is involved and everyone goes counter-clockwise around an oval.

Unlike other sporting events where all the focus is on the competitors, the Derby is as much about the crowd as it is the horses. Celebrities, big hats and designer dresses and suits are all part of the unique Derby atmosphere. So with that in mind, here are a few tips for those attending the Most Exciting Two Minutes in Sports.

Guys, Keep it Classy

When you go to the track, what do you usually wear?  If you’re a typical guy, depending upon where you live, it’s probably jeans or shorts, a t-shirt or maybe a polo shirt, and some sort of comfortable shoe or sandal (if the latter, hopefully, sans socks).

(Photo via

(Photo via

That doesn’t fly on Derby Day, especially if you’re taking a lady — yours, someone else’s or a friend. Save the t-shirts and shorts for the Kegasus fest at the Preakness. The Kentucky Derby is all about class. Any ticket better than general admission or the infield calls for it.

Yes, that means a suit, dress shoes (with socks) and a tie. If you want to make a good impression, match the tie colors to what the lady is wearing. If you really want to make an impression, wear a hat. No, not a beer holder, a fedora.

Stop whining.

The noose, er, tie can come in handy later if your betting picks land you in the red.

Men with general admission tickets without a seat can skip the tie and dress a bit (just a bit) more casually — sport coat, either collared shirt or polo, and khakis.

If you’re in the infield, well, just about anything goes.

As a guy, at least you have it easy figuring out what to wear.

Ladies, Do’s and Don’ts

Fashion magazines are what we grew up with; they were our style bibles and taught us everything we knew. Who could ever forget Glamour magazine’s “Do’s and Don’ts” with the hysterically funny black bar partially obscuring the poor victim’s face who found herself in a national magazine as a “Don’t?”  I eagerly awaited each month when a newly minted tome would arrive, heralding in the next month and new season of fashion.

When dressing for an event as specific, timeless, and traditional as the Run for the Roses, I can’t help but go back in my mental Rolodex of Glamour “Don’ts” and think how they might apply here. Of course, it’s easy to say wear this, don’t wear that, but let’s dig a little deeper so we are sure to put our best pedicured foot forward on the first Saturday in May.


(Photo via

(Photo via

Let’s talk about the day dress. One of the biggest “Don’ts” I see at the Derby is that women who mistakenly think this is the time for dressing like they are going to the hottest nightclub in Manhattan or Los Angeles. This is especially prevalent among the twenty-something crowd. For those thirty-somethings and older, there is no need to show endless amounts of skin at the races, even if you think you have the body for it — major Don’t. At this stage, we’re most likely not going to be in the infield with the throngs of frat boys and sorority girls chugging on beer pongs. You don’t want to be the woman everyone points at and says, “her old @#^* should know better.”

The Don’ts include club-wear: skin tight, high-thigh-baring miniskirts, daringly low-cut dresses, over-the-top sparkly or sequined cocktail dresses, skimpy lingerie-inspired slip dresses, 6″ stiletto heels and heavy makeup. Add to that too many mint juleps and you’re teetering around the track looking like, in the words of my ultra-chic and perennially fashionable aunt, a “shameless hussy.”

I’m not saying wear a plain, boring, solid-color straight dress with no embellishments.  It’s definitely not the office or the boardroom. Now more than ever, the style options are endless. So by all means use imagination, your own sense of personal style, and a touch of whimsy to put together a classy, original and standout look.


(Photo via

(Photo via

Keep it simple. It’s a long day. Wear a dress that fits you today, not one that would look great when you lose those pesky ten pounds. You don’t want to deal with the too-tight, constricting, riding up, tugging and pulling down or fiddling-with-straps pitfalls we’ve all experienced.

A light, flowing spring dress or a classy sheath is perfect. The great thing about the flowing fit and flare style dress is that it is universally flattering. It’s a super-comfortable style to wear all day while accentuating the waist, and playing up any curves you may have. Fit and flare dresses in a floral print or bright color are your best bet on Derby Day.

One of my other all-time favorite silhouettes is the classic sheath dress. In our mothers’ day, it was known as the wiggle dress. It’s a figure-flattering look with clean, classic lines that is modern, sexy and understated at the same time. There are so many variations on this classic.

Peplums are a great addition — abstract flower prints, modern contrasting piping, embroidered trims, and lace detail to name just a few. Every fashionista you see running around during Paris fashion week will inevitably be wearing a version of this dress. Think about the appeal of a woman in a pencil skirt and heels. The sheath dress is nothing more than a pencil skirt with a top added. Pair it with a light jacket or shrug for cooler days.

It’s All About the Hat!

(Photo via Christine A. Moore Millinery)

(Photo via Christine A. Moore Millinery)

Which comes first, the hat or the dress?  Fortunately, hats are “in” right now, even when it isn’t Derby Day. There are as many styles of hats and fascinators as there are dresses.

The Kentucky Derby is all about the hat. If you have never worn a hat and are shy about doing so, don’t be. Perhaps, if this is your first Derby experience, you are a neophyte, or hovering under the age of 20, you could be excused for wearing a floppy hat, or worse yet, no hat at all (the horror!). But in the hallowed grandstands of Churchill Downs, looking your best will make the experience special. You will feel confident as you stride amongst the beautifully turned out ladies and men to not only attend one of the greatest parties ever, but to watch the best 3-year olds in the country compete for the prestigious gold trophy, the $2 million purse and a shot at the Triple Crown.

(Photo via

(Photo via

A friend of mine adamantly proclaimed for many years: “I don’t look good in hats! I’ve tried them on, I don’t like them, I look silly in a hat.” Then, she met Christine Moore, the Official Kentucky Derby Hat Diva who has been christened “The Milliner to the Triple Crown” by NBC Sports. Christine knew exactly how to fit my friend for a beautiful, elegant hat that could take her to the races, an event at the country club or even to church. My friend is now a mad hatter; the last time I checked, she had purchased two more.  No matter your size or shape, the right hat gives you and your outfit an instant lift.

To go with your comfy, flowing spring dress, choose a beautiful Parisisal Straw wide-brimmed hat, trimmed in a glamorously show-stopping oversized silk bow. Another option is an ultra-feminine wide-brimmed hat with fluttering silk roses, ruffled edges, and French netting. If you prefer to wear a fascinator, chose a simple one that mirrors the colors in your dress.

You can get away with practically any style hat, fascinator/hatinator when wearing a simple sheath dress.  They are sculptural, statement-making and gaining in popularity in the U.S., as we see how fashion-forward and altogether stunning the ladies at Royal Ascot, the Dubai World Cup and Melbourne Cup look on race day.

Shoes and Accessories

(Photo via

(Photo via

Unless you’re sitting in a seat and are fortunate to have someone at your beck and call, you’ll be on your feet a lot during Derby Day. The trek from the parking lot alone can feel like a marathon. During the day, you’ll be standing in long lines at the betting windows, standing in lines to order food and drinks and standing in line to get into the bathroom.

Wear low sandals — no greater than a 3-inch heel — or chic flat. As you probably have learned, an all-day event with lots of walking and standing is not the time to break in new shoes. They will break you in first.

When you’ve got a lot of pattern going on in your outfit, it’s best to keep the hat in a simpler shape, with fewer embellishments, picking up on one or two colors in the dress. If you opt for a solid color, a bright or jewel tone works well, contrasted with something unexpected, like a patterned shoe, a statement necklace, big hat or embellished fascinator.

Be careful with accessories. In the immortal words of Coco Chanel, before you leave the house, look in the mirror and remove one accessory. Because a big, flowered Derby hat is a statement unto itself. In the case of accessories, less is more. You don’t need dangling chandelier earrings, plus a necklace, plus the flower and feather-embellished hat, stacks of bracelets, fringed high heeled sandals and a beaded clutch. It’s like spangles on top of spangles everywhere the eye can see. It overwhelms and confuses the look. The most stylish ladies always edit. 

The Best Thing to Wear

The best thing to wear to the Derby is your own brand of personal style. It’s not about slavishly following the latest trend or what the hottest celebrity is wearing. A sense of self confidence, an adventurous spirit and a great group of friends to share race day memories with will ensure you have a winning day!

See you at the races… if my hat isn’t too big.

Laurie Ross
Laurie Ross is a handicapper, pedigree consultant and published author. She is also a member of the National Turf Writers and Broadcasters Association. Laurie maintains her pedigree website Iron Maidens Thoroughbreds and pedigree handicapping blog, IMTBreds, where she focuses on two-year-olds and maidens through the Triple Crown Trail.

Since 2008, Laurie has been a featured writer and pedigree analyst with Horse Racing Nation. Laurie’s yearly publications contain tremendous insight and value for bettors and horsemen. The Freshmen Sire Guide has received accolades from leading trainers and handicappers. Her Triple Crown e-books continue to be a best-selling feature. Laurie’s work has been featured on numerous websites and she is a recurring guest on sports radio programs.

Laurie has been around horses for most of her life, working in racing stables as a hot walker and exercise rider in her teenage years, and later as a volunteer with rescued and retired racehorses. She attends thoroughbred auctions year round on behalf of clients and manages the breeding operations for a racing/breeding syndicate.

Posted on

Proudly featured on: