First Timers' Guide to the Kentucky Derby

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The Ladies Guide on How to Dress for the Kentucky Derby


It’s that time of year again! April is here meaning the 2014 Kentucky Derby is just a few short weeks away! Now, I know what you’re thinking. What do I pack? What do I wear? To wear a hat or to not wear a hat? Don’t worry! We’ve got you covered, ladies.

We’re going to help you plan the perfect Kentucky Derby outfit so when the first Saturday in May rolls around you’re ready! Read on to get an idea of how you should dress for the Derby this year, and don’t forget to bookmark the page so you can come back to it when you’re packing your bags in a few weeks!

The Gentleman's Guide on How to Dress at the Kentucky Derby>>>

It All Starts with the Hat!

First up on your Kentucky Derby fashion must have list is an epic hat! Horse racing draws in a unique and high fashion crowd, and since American horse racing draws from its British ties, there is a large amount of pageantry aligned with the sport. There is just as much interest regarding who attending the race and what they wore as there is about the actual race!

So what does this mean? It’s time to bring out your most elegant attire and polish it off with a hat!

Derby Experiences Kentucky Derby Fashion and Pagentry Womens Hats

Wearing a hat to the Kentucky Derby will not only add a certain class to your outfit that will help you fit in around Churchill Downs, but it’s also a great way to show your creativity! All kinds of hats are seen at the Derby! Hats donned with ribbons, bows, flowers, tulle, frills and flowers alike can all be seen inside Churchill on Derby day. And remember, the bigger the better!

Not to mention, your hat will work dual purposes to protect you from the Kentucky sun while you’re outside at the track on race day.

Plan the Attire!

253197 582842058415701 1049257181 nWomen’s Kentucky Derby fashion continues to change with the ages and becomes more modern year after year. But with that said, there’s always a sense of class and elegance to the attire to keep with the tradition of the Kentucky Derby.

Whether you’re in the mood to wear a maxi dress, short dress, flowy skirt, pencil skirt, pants or a romper, they will all be seen at the Derby. However, there are two things to remember when picking your outfit:

  1. Pick something cool and comfortable – the Kentucky Derby is held in May so the weather is likely to be warm, and once you get to the track, changing isn’t an option. You’ll want to make sure you select an outfit that you’ll be comfortable wearing all day.
  2. Plan around your Kentucky Derby hat – don’t forget that your hat is your biggest feature at the Derby! Spring patterns are fun, but you’ll want to select an outfit that doesn’t contrast with your hat. When in doubt on whether or not your outfit goes with your hat, it’s safer to go with solid colors.
And don't forget if you're also attending the Kentucky Oaks, include the color pink in your outfit choices!

Don’t Forget to Accessorize!

972123 582837891749451 1909942563 nAccessories are a big part of dressing for the Kentucky Derby; after all, they complete your outfit! When choosing your accessories, it’s important to remember to compliment your outfit and don’t select anything to loud that it draws attention away from your main accessory, your hat.

A few necessities you’ll want to remember? A small purse to hold your personal items (you can go for a bigger purse, but remember you’ll have to hold it all day), sunglasses and jewelry! When selecting your jewelry, remember, it should make a statement, but not pull focus.

And last, but not least, footwear. When you’re seeking an outfit that screams class, it’s natural to want to pair it with your best pair of heels. But unless you’re used to walking in heels all day, we wouldn’t suggest this.

Churchill Downs is a large track and you’re guaranteed to be on your feet all day long, so search for shoes that go great with your outfit, but also offer comfort. Opt for a pair of flats or wedges that will be kinder to your feet than those stilettos. And if you are determined to wear those pumps, purchase some gel insoles to add cushion throughout the day. Trust me, your feet with thank you!

… And You’re Kentucky Derby Ready!

The important thing to remember when selecting your 2014 Kentucky Derby outfit is that you want to match comfort and fun with your own sense of style! If you have any questions about planning your perfect Kentucky Derby outfit or if you’re looking for more style tips, let us know in the comments below.

Get More Kentucky Derby Fashion Tips

How to Look Chic at the Kentucky Derby [Women's Fashion Edition!]


When people hear Kentucky Derby™ two things usually come to mind: Horses and Fashion, specifically those hats!

My first glimpse at the spectacle that is Derby Fashion came during one of my all-time favorite movies, Pretty Woman. Who doesn’t remember that scene with Julia Roberts wearing a gorgeous, belted, brown and white polka-dotted dress with crisp white gloves, beautiful earrings and a matching white hat (with polka dot detailing)? Although times and fashion have changed, this still remains the recipe for a great Derby Day outfit.

Kentucky Derby Fashion: Julia RobertsDerby Fashion: Modern Day Julia Roberts 

The Hat

You could probably show up to the Derby in a garbage bag, as long as you had a fabulous hat to match! (We’re just kidding about the garbage bag) however, the hat is as much a part of the Derby as the race itself.

Derby Fashion: Elaborate Hat Derby Fashion- Pink Hat Derby Fashion: Feather Hat

Hats are usually wide-brimmed to protect the wearer from the sun, but also to accommodate all the ornate accessories and embellishments usually laden upon it. Some choose simpler hats with a single flower or ribbon accessory.

Derby Fashion: Feathers and Tulle Hat

Others go all out including a combination of different flowers, ribbons, feathers, tulle, bows, frills and just about any other design element you can think of! With a Derby Hat your imagination and creativity are your only limits.

Derby Experience: Derby Hat Derby Experiences: Elaborate black and white hat


The Dress (Skirt or Pants!)

While the tradition of Derby Hats has remained consistent the standard for an outfit has changed. It’s a safe bet to go with a simple but well fitting dress (let the hat steal the show), however as fashion has evolved, so have the outfits seen at the Kentucky Derby.

Derby Fashion: Maxi Dress Hat  Derby Experiences Fashion: White Pants

Guests are now more daring and some great Derby Fashion moments have been born from those adventurous few. Maxi dresses and rompers which have never been the norm, look amazing paired with a Derby hat. Also a pencil skirt or full skirt with an in-season neon top and simpler hat would fit in at Churchill Downs.

At this year’s Macy’s Kentucky Derby Festival Fashion Show, the runway was populated by dresses but surprisingly shorts made a well-received appearance as well. Proving that fashion this year will be varied, unpredictable and fun! 

The Accessories

If you want to be the topic of a blog like our girl, Julia, then do as she did and accessorize! Her gloves, belt, jewelry and shoes made her outfit. It’s not uncommon for ladies to wear gloves of lace or other materials, and the skinny belted-dress trend will certainly be seen a great deal at Derby.

Derby Fashion: Casual Sandals HandbagDerby Experiences: Sophisticated Derby Fashion


Other accessories to keep in mind are jewelry and shoes. Jewelry such as watches can serve two purposes of both practicality (don’t want to miss those post times) and fashion. Also donning the in-trend statement necklaces, earrings or more unconventional pieces can add to your Derby Day look. Shoes will range from sky high heels to comfortable, cute flats or sandals. Personally I like wedges, as they give you great height and are usually kinder to keep your feet in for an entire day versus regular heels.

Derby Fashion: Sunglasses

Finally as a note to the practical: sunglasses and shoulder bag would be a great way to complete your outfit, protect your eyes and store all your stuff (also it’ll keep your hands free for cheering and holding Mint Juleps!)

The main thing to keep in mind is that Derby Day fashion is about incorporating your own style into the traditions of Churchill Downs AND having fun!


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