Whether you’re a Kentucky Derby regular or it’s your first time at this grand “Run for the Roses” event, you’re going to need a master plan to look your Derby best this year.

This sporty weekend at Louisville isn’t just about racing thrills – it’s an outright fashion tournament and we’re here to arm you with the best style tips to glam hard at the historic Churchill Downs Racetrack.

The first lesson? Pay special attention to your hat and keep it unapologetically flamboyant! That said, it’s now time to plan your Kentucky Derby outfit. But first…

What is the Kentucky Derby?

The Kentucky Derby is the longest-running and (the most thrill-inducing) sports event in America. It unfolds every year on the first Saturday in May. Held at Churchill Downs racetrack in the good ol’ Louisville, this event features a race of three-year-old thoroughbreds across a distance of 1.25 miles. Each year, the winner takes home a grand blanket of 554 red roses, which is why the Derby is also dubbed “The Run for the Roses.”

Why the massive spotlight on fashion for a racing competition, you ask?

Over 150,000 ultra-stylish fans flock to Louisville, flaunting their over-the-top hats and extra-stunning outfits to watch these “greatest two minutes in sports.” So, looking your absolute best at the event is non-negotiable.

How Should Women Dress for the Kentucky Derby?

Here’s your no-fail guide to piecing together a Kentucky-Derby-worthy outfit:

The Dress

  • Patterns and Prints. Prints and patterns are the most important Kentucky Derby signatures. Floral designs, stripes, and polka dots are three of the most popular choices for patterns. If you’re picking a patterned piece, ensure that it comes combined with a bright color.
  • Most Kentucky Derby outfits feature a heavy dose of floral prints and polka dots. But if you choose to stick to no-print pieces, go for single-colored outfits or pieces painted in bright or pastel hues. Red is the most popular choice for this event because “red rose” is the official Kentucky Derby flower. Hues like shrinking violets or dull nudes have no place on the track. Instead stick to shades like bright yellow, pink, indigo, orange, purple, blue, and greens.
  • Length and neckline. Go for lengths that are knee-level, mid-calf, or above the knee. Pick flowy pieces or stick to the popular figure-flattering A-line dress. As for the neckline, a Bardot neckline is an excellent choice.

The Hat!

Hats are a must-have item for this sports event for both men and women. A simple “rule of hat:” Go big or go home. Your hat can never be too over-the-top. In fact, the more flamboyant it is, the better. Just be sure to match the hat with your overall outfit. For instance, if you’re donning a solid-colored dress, get yourself a hat that flaunts florals complementing the color of your dress. If your dress features loud patterns, pick a minimalistic hat to balance your attire.

The Accessories

Your hat is undoubtedly going to steal the spotlight at the derby. To avoid any other outfit element from clashing with your jaw-dropping headpiece, steer clear of statement pieces. As for the bag, follow the Derby’s rule of carrying a purse that’s not over 12 inches in height or width. Luckily this size is just enough to toss a pair of flats in if your heels get too overbearing.

The Shoes

The sunny May day of the Kentucky Derby is going to be hot and humid. There will be lots of standing and walking. You want to make sure the pain in your feet doesn’t distract you from the awesomeness of the event. So, ditch those stilettos and pick something comfier like block heels, flats, wedges, or even flip-flops!

The Hottest Kentucky Derby Trends

Bright colors, pastel hues, floral patterns, stripes, fancy hats, and comfy shoes are a timeless Kentucky Derby trend.

Looking for the hottest Derby trends this year? Kentucky Derby’s official page says there will be “a lot of powdery, icy pale blue,” and “florals with a plethora of 3D surrealist embellishments and motifs” will rule the Derby this year. They also add, “polo shirts, sports blazers, and preppy plaids will be prevalent!” For shoes, “the breakout star of this summer will be wedges!”

A Few Life-Saving Tips for the Derby

Consider the weather when picking out your outfit. Louisville May days can be hot and sunny, cool and rainy, or a combination of both types. The safest option here is to choose fabrics that are breathable and comfortable such as linen, cotton, silk, and gauze.

Because you can never know how exactly Derby Day will unfold weather-wise, be prepared with three different outfit options:

  • Dress or jumpsuit.
  • A shrug or wrap (if morning or evening temperatures drop).
  • A rain jacket or poncho and rain boots (if it rains).

Because comfort is a priority, it’s recommended to ditch the shapewear and welcome breathable outfits instead. This doesn’t mean you can pick a pair of jeans and athletic shoes. The sun will be shining over your head throughout the day so don’t forget that sunscreen. Keep your makeup setting spray handy to ensure your makeup looks fresh all day.

What Should Men Wear for the Kentucky Derby?

Similar rules apply to men when dressing for the Derby. Go for a bright pastel or tropical-hued shirt, pair it with a lightweight sports jacket, and finish off the ensemble with a colorful bowtie or necktie.

If you’re looking for the safest possible option without having to piece the entire outfit together, go for a seersucker suit! Not only are these suits a traditional Kentucky Derby choice but they’re also perfect for staying super-comfy during the hot and humid race day.

Over to You!

Whether you’ll be sitting in the grandstand or watching the thrill unfold from the infield – make every attempt to look stunning on Derby Day. Shoot for bright hues, let your hat steal the show, and wear comfortable shoes so nothing can stop you from having the best time of your life.

If you haven’t decided on what to wear to the Derby already, we suggest you start finding an outfit ASAP! Head over to New York Dress now to snag that designer floral beauty and look like a million bucks!

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