The 411 On Stylish Kentucky Derby Outfits for Race Day

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Facebook, Fashion at the Races

The Run for the Roses is one of the best days to show off your love of luxurious fashion and feel like a Southern King or Queen for the day.

For decades, the Kentucky Derby and Oaks has been an event for fashion lovers to come and strut their style in their best Kentucky Derby outfits for the world to see. I mean, sure - the Derby IS about seeing horses race to obtain the winner title along with a few great prizes. However, the true phenomenon is the fashion and luxurious outfits we all get to dress in and see.  

Both female and male attendees pull out all the stops when selecting their Kentucky Derby outfits. It's the chance for every female to channel her inner Southern Belle and every man his Southern charm. In fact, it is the ultimate fashion event to let you (and everyone else) know that spring has finally sprung! Trust me, it’s an event you don’t want to miss when it comes to chic apparel.

Kentucky Derby Outfits Over Time

Horse racing and fashion have been tied together for centuries. The prominent fashion first started when Col. Meriwether Lewis Clark Jr.  had a vision for the Derby and Oaks that extended far past horses and racing. He thought of it as a social affair that the high-class could attend. This luxurious happening set out to be equivalent to European style racing events -- which mandated full morning dress for men and women.

During the first running of the Kentucky Derby, Meriwether actually used high-class women to recruit the type of clientele he wished to have at the race. With these women flooding the crowds, fashion quickly became just as important as the racing. To some, even more important! Being so, these women grabbed the opportunity to show off the latest spring fashion by synchronizing their hats, dresses, shoes, bags. While the popular styles may have changed, the focus on fashion certainly has not!

1920s

In the 1920’s, women at the Derby were seen wearing mainly dresses. However, daring women also wore modern suits, finished with a pairing jacket. The dresses were typically of a longer length and became a favorite for the Derby. To top off their Kentucky Derby outfits, the women added accessories such as hats and gloves. Men generally wore formal attire and let the women shine.

1930s to 1940s

This time frame didn’t change much from the previous years except for more women deciding to wear pants and suits. Formal was the way to go and man did they look bold! Back then, many of the jackets had ample space and room -- making them comfortable and hospitable. Even though those were the trend, of course there were also fitted jackets.

1950s

The 1950’s was an exciting time for America. The war had just ended and fashion mirrored those changing times. At the Kentucky Derby, many of the views consisted of women wearing chic suits that included skirts fitted to the body or swelled outward with help from a petticoat. Dresses became colorful and hats with gloves continued as a trend.

1960s

This is the time when hats and colors started becoming what you see at today’s Kentucky Derby and Oaks. Yes, women still dressed up in distinguished clothing for this respectable event. However, since Millionaires Row inception, high society women started wearing more spectacular hats.

The hats were bigger, crazier,  more colorful, and one for the eye to see. Fashionable women took pride in their hats and enjoyed picking them out to complete their Kentucky Derby outfits. As hats and gloves started to fade in the fashion world, the Derby allowed society women to continue these traditional trends. Besides the hats, prints, patterns, and colors were louder and hemlines rose.  

1970s to 1980s

At the 1970’s Derby events you could see a return to longer skirts for women. Other than that, the new casual attitude from the 1960’s remained the same. So much of the clothing was full of patterns, colors and grandeur hats.

1990s to Present

Through the 1990’s, women at the Kentucky Derby continued bringing dresses back to the front line where they belong. Of course there will always be women who wear suits, but dresses were (and are) most common -- especially with the younger crowd. By this time gloves basically dropped off the face of fashion. However, hats will always be in style.

For this reason, the hats have become the main show of the entire Derby event. They continued to get bigger, brighter, and more enthusiastic. On the other hand, clothing style seemed to relax a bit. Especially in the infield with women wearing cool sundresses, shorts, and cotton skirts.

How to Dress: Kentucky Derby Outfits 

There are NO rules when it comes to dressing for the Kentucky Derby and Oaks. That being said, there are some important considerations to make: 

Color Palettes

Phenomenal fashion will seep into your system as you take in the fabulous view around you. Most Kentucky Derby outfits will have wondrous, bright colors. Many of these include pastels, greens, blues, pinks, etc. Leave any black and white or dark colors for fall races later down the road. You need to remember - it's SPRINGTIME! Floral print or patterns will NEVER be wrong at the Derby and Oaks.

Check the forecast!

Something you won’t want to forget about when deciding what to wear is checking the weather. Weather in Kentucky can change day to day and even throughout the day. That is why it’s important to stay up to date with what the expected weather will be like so you can make sure you dress accordingly. Best tip would be to always check the weather in advance before gathering your Kentucky Derby outfits.  

Dress Code by Section

While there are no specific limits on what you can or cannot wear, certain sections and areas do require a particular type of attire to be worn. Below are those sections and what you are expected to wear there.

Boxes in the Trophy Room, Turf Club, and Millionaire's Row

These areas will be between air-conditioned dining rooms and outdoor terraces -- some covered, some not. Business casual is required if you'll be watching the race from any of these sections. Crazy colors, gold, ruffles, and patterns will do you justice.

Women, dresses are the best option for you -- but a business casual suit would be okay too. Guys, you must have collars on your shirts. No athletic shoes, denim or inappropriate clothing is allowed. In the Derby Room and The Mansion, jackets are also required.

Clubhouse and Grandstand Seats

Casual attire is permitted in these areas. Even so, the chances of you seeing casual dress are slim to none. It's completely understandable though. Part of the fun is for everyone to dress up in luxurious, chic fashion at this affair. Be mindful of these sections though. Their areas have stairs and such, so think of comfort if possible.

Infield

For those of you in the infield, there is no dress code. Just as the above section though, some of this crowd will also want to dress up. You’ll be doing a lot of walking and sitting on the grass (or mud). So if you’re going with heels, they should be practical (wedges work well!).

The Major Fashion Components for Women and Men

As mentioned, there are no rules to dressing at the Derby and Oaks. Yes, you do have to wear business casual apparel in certain areas as listed above. But otherwise, there are no particular limits on colors, patterns, styles, or anything else!

There will be plenty for your eyes to feast on -- such as dresses, rompers, skirt suits, suits and more. Along with the clothing, you will see the most extravagant of hats. Mainly because they are the most important piece of clothing or accessory at these renowned races.

Women

Dress or hat. Hat or dress. Which comes first when picking our overall outfit? The real answer lies with the Derby fashion Gods, because with us common folk, many disagree. Some say you should get your clothes first and then design and coordinate your hat to match. Others say pick out or create your hat first (because it’s most important in Derby world) then coordinate your clothing with it.

Which one is correct? What should you do? Well, I say don’t worry -- be individual and do whatever you want! Look ladies, in the end, your entire Kentucky Derby outfits must tie together. So whether you synchronize the hat with the dress or the dress with the hat, it needs to blend in a sweet, harmonious vision. So how you get there? Doesn’t matter! Just make it work and make it tremendous!

Dresses

Since hats are famously known at the Kentucky Derby and Oaks, most make them the main attraction of their entire outfit. Meaning, you should pick amazing clothing but keep it simple so it doesn’t completely take away from your hat. Kentucky Derby outfits should be centered around Spring. Incorporate a dress full of bright colors and fun floral or equine patterns -- they never disappoint.

Remember, this day is all about channeling your inner Southern Belle. A bold style is specifically good for those who would rather have their dress be the main conversation piece. Interpretation varies, with women sporting anything from a strapless sundress to mid sleeves, jumpsuits and rompers. Dress length bears no rules but stay classic and keep it just above the knee or mid-calf. Too short doesn’t fly at the Derby and Oaks!

Shoes

Kentucky derby outfits for women are never complete without a stunning spring heel or sandal. Want to wear a super high heel or stilettos? DON’T! Churchill Downs historic territory can be dicey to navigate due to cobblestones and other surfaces. Now if you can’t live without some type of heel, choose something lower with more surface coverage. Not to mention, it’ll be more comfortable with all those long lines and walking.

A few options I enjoy that go well with the luxurious Southern style are open-toed heels, gorgeous summer sandals, or a chunky pair of espadrilles. These will provide support throughout the lengthy day while keeping you looking chic as ever. Another tip is to bring a backup pair of flats in case you want to give your feet a rest. Just make sure those are stylish too!

Hats

Part Southern tradition, part extravaganza, the Kentucky Derby and Oaks hat parade is exactly what makes the “fastest two minutes in sports” so unique to watch. Crazy hats became associated with the Derby and Oaks back in the 1960’s when social fashion norms slackened. Attire became brighter, enthusiastic and more ornate -- and what we're really talking about are hats.

Fascinators also came out in 2011 and have been making a grand appearance ever since. If you’re curious about fascinators, they are a for sure yes! Even though they are more of a recent trend at the Kentucky Derby, they bring the shazzam that is expected of your headwear.

In my opinion, they’re fabulous. And we have Kate Middleton to thank for these elegant pieces of art! Plus, they are much easier to wear than a hat and on top of it all they won’t give you horrendous hat hair!

Breathtaking, elaborate and fashionable -- each hat makes all Kentucky Derby outfits astounding. Typically, women wear wide-brimmed hats that hold a Southern Belle charm. Many of these hats are decorated with bows, ribbons, flowers, feathers and more.

When it comes to the infield area, hats are even more idiosyncratic! We have seen hats with dolls, flamingos, horses and more rested atop of them -- always giving you something to be surprised by! You can go for something simpler if you want your dress to stand out, but most like their hat to be the main attraction. Either way, try and find something that isn’t too hot and heavy.

Derby hats need to look stunning, chic and lavish. Buying a high end piece of headwear is always a great choice, but creating your own is the perfect option too. Look online or go to the store and find a regular wide-brimmed hat. Once you get the hat, top it with ribbons, flowers, feathers and more. Honestly anything you want can work, as long as it’s elegant and a show stopper!

Bags

Southern queens, bags at the Kentucky Derby and Oaks should be simple yet chic. Taking away from your Kentucky Derby outfits is not something you want to do. Best options include a stylish tote or clutch that matches well with your entire outfit. However, other than keeping the purse simple to let your ensemble stand out, there are no specific style rules.  

The Derby website does have size restrictions on bag and purse size though. Those restrictions include a bag that is no larger than 12 inches in any dimension. My recommendation is to bring a larger bag if you plan to carry any essentials for the day. That way, extra shoes, your program, sunglasses, and other necessities are always on your person. A clutch works too and is perfect to hold cash for quickly making a wager.

Jewelry

Let your hat be the main attention point at the Derby and Oaks. Keep any and all jewelry plain, simple, and small -- but still completely beautiful of course. Depending on your outfit, the jewelry can vary. Some Kentucky Derby outfits might call for a gorgeous strand of pearls while others need exquisite silver bangles and earrings. No matter what you choose, make it unified with your overall look.

Men

Back in the day men might not have taken fashion as seriously as the women did. But in today’s Kentucky Derby world, you can bet they pull out all the fashion cards too! It is the perfect excuse for men to get dressed up just as much as the ladies do and man do they love it.

Vibrant hats and animated suits flood the Clubhouse, Millionaire’s Row, and the infield. Just as the women, men partake in wearing pastels and stimulating colors in expression of Spring. Their apparel includes tropical vibes, loud plaid, and fearless stripes. Trust us, if you’re a gentleman going to the Kentucky Derby or Oaks, you’ll want to join in on this festive fashion!

Pants

For men at the Derby, pants should be in sun drenched, rich colors. My favorites would include the classic key lime, blue sky, orange and bermuda pink. Pastel chinos are a crowd favorite and other linen trousers will do you just fine as well. Any of these options accompanied by the perfect shirt and blazer will make you the best looking guy around.

Shirts

Great dress shirts are very important for men at the Kentucky Derby and Oaks. Choosing to wear a quirky jacket means you should keep your shirt on the simpler side. On the other hand, if you keep your jacket simple go ahead and pick a patterned shirt to add some contrast to the color of your pants and jacket. Good options for a shirt include striped or gingham. Suspenders also add a nice touch to any great dress shirt!

Jackets

Jackets are a must at the Kentucky Derby - even being mandatory in the Mansion and Derby Room. A jacket is what brings all the Kentucky Derby outfits together. You’ll never go wrong with a classic navy blazer. Still, finding something with a unique pattern that gives everyone something fun to talk about.

Now if you want something uppity that’s not too out there, grab something striped to remain fun yet chic. A seersucker will never be wrong and is my favorite choice for any of you gents going to see the Run for the Roses this Saturday.  

Ties

Usually the majority of men wear neckties. Go with something simple if your jacket or shirt is patterned and stands out. If your jacket and pants are more subtle, choose a patterned tie. Bowties have also become a norm and make all the Kentucky Derby outfits extravagant. The same rules apply for the bowtie as the necktie when matching it to your complete look. Vineyard Vines is the official tie maker of the Kentucky Derby and can help you pick the perfect tie.

Hats

To complete your ensemble, you must include the perfect hat. As we’ve explained throughout this entire article, hats have become a legend at the Kentucky Derby and Oaks. Men typically wear a luxurious fedora or bowler hat to give themselves that perfect Southern gent appeal.

Safe bets come in a solid color and have been inspired by the fashion styles of the 1920’s. Others have feathers, bows and more exotic features. If a loud statement isn't your speed, the traditional and classy can take you a long way paired with the perfect outfit.

Shoes

The most important thing to mention about any type of shoe you wear at the Derby is that you MUST wear them sock-less. You will be the odd man out and might catch a few silly looks if you don’t! Besides that, there are numerous types and styles from which to choose.

If you are wearing a suit, I enjoy penny loafers. They look great and pull together the entire outfit above. Horse bit loafers are specifically good for the Derby. Wingtips, oxfords or strap shoes would also work well. Just remember, NO SOCKS!

The Longines Fashion Contest

To prove how important fashion became at the Kentucky Derby and Oaks, they even created a contest. Longines is the official partner, timekeeper, and watch of the Kentucky Derby, as well as the the Longines Kentucky Oaks.

Just as Churchill Downs, Longines believes “elegance is an attitude”. They promote the sophisticated look shown at the Derby and Oaks and renewing their fashion contest invites even more women to look their most elegant and chic.

Maximize your chances of winning.

For the contest, hats and fascinators continue to be the most important and traditional accessory on Oaks fashion day. Although hats are central, all Kentucky Derby outfits should be on point.

Pink is the color of the day. All guests are asked to incorporate it in their clothing to help raise funds and awareness for breast and ovarian cancer. There is even a march, the Survivors Parade, that takes place on the racetrack prior to the Kentucky Oaks race. Due to this, make sure you pull out all the pink you can for awareness and to earn those extra points for the contest!

Wondering what you’ll get for winning this fashion contest? A beautiful timepiece from Longines, of course! Walking away with a heavier wrist is nice, but we think the bragging rights of being the best dressed at the Kentucky Derby reigns supreme.

Overall, the Kentucky Derby has become a place to see and be seen.

With numerous Kentucky Derby outfits for your eyes to behold, there will never be a dull moment when viewing the crowds. All colors of the rainbow will collide together as they become one picturesque sight. The Kentucky Derby outfits flooding Churchill Downs are a true spectacle that you will never want to miss.

Are you going to the Kentucky Derby and Oaks? If you are, what are you wearing?

Even if you’re not, do you plan on watching? Say you could go, what would you wear then? Tell us in the comments below and share with all the fashionistas in your life!  

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