Guide to Derby Attire Part One // The Classic Chic

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The Kentucky Derby is weeks away, and I sent out a poll in my Instagram stories questioning my readers whether they would be interested in my take on dressing for the derby; the results were overwhelmingly positive I’m happy to report! 

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The Kentucky Derby is a horse racing event (yes, classified as a sport) that takes place the first weekend of May at Churchill Downs in Louisville, Kentucky. Horse racing has long been an elite gathering to socialize, bet on horses, and drink mint juleps (read my favorite recipe here!). The Kentucky Derby is the first leg of the American Triple Crown and is followed by the Preakness Stakes and the Belmont Stakes. The Kentucky Derby has been run every year since 1875! They still ran the races during both world wars, in fact. This tradition is not only about watching 2 minutes of horse racing history go down--the derby is a social event that welcomes individuals from either end of the spectrum, from the drunken college students in center field to the most upper crust socialites and celebrities in the Millionaires Row.

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That's what is so grand about the derby. It serves as an opportunity to put on your Sunday best, don an incredibly ostentatious hat, and wine and dine with the finest! Sounds like an environment I'd thrive in, right? ;)

So you're going to the derby, or you've settled for a fabulous watch party instead (same concept, but about $600 cheaper!).

Now what to wear?

For starters, you need to decide whether your outfit will be inspired by your hat or vice versa. I personally like to decide on a color scheme and go from there: do I want to be monochromatic, caught up in the little details, or keep it simple with a daring hat? Of course, you can go with all three.

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For example. One year for the Belmont Stakes, I opted for black scalloped dress shorts, a black lace camisole, black silk tuxedo jacket, black fascinator with a sleek pony tail, and black lace gloves. Y'all, heads turned. Probably because Long Island had no idea what kind of creature was walking into their relaxed midst! I emphasized a monochromatic look with intimate details and a unique fascinator. 

If you're beginning with your hat, here are some tips to follow:

  • Fascinators are all the rage every year. But opt for a wide brimmed hat if your seats are in the sun. 

    • The derby is an outdoor event. Let me repeat: the derby is an outdoor event. You will be uncomfortably warm if you are under the mezzanine covering, and unbearably hot if you are out in the open. So dress accordingly! Fascinators are a wonderful alternative to big hats and look extremely contemporary and chic, but they offer zero protection from the sun. If you know you will be exposed, I suggest the largest, widest hat possible! You'll turn heads (in a good way) and keep your shoulders from burning in the process. 

  • Hats with accessories (feathers, flowers, etc.) are encouraged, just be courteous of your neighbors. 
    • I adore hats with feathers or any sort of embellishments. However, you will be walking around a lot and brushing up against people (and other enormous hats). Keep in mind that embellishments may fall off or invade what little personal space other derby-goers may have. Tall feathers may breach the view of any spectators behind you as well. Better stick to a low-threat design!
  • The derby is no place for a simple, straw beach hat. Be loud, fabulous, and daring!
    • With the above bullet point being said, the derby is no place for your vacation hat that you throw on with your cover up! I see so many women make this mistake each year. A simple straw hat is very anticlimactic for the rest of your ensemble, and the atmosphere of the event in general. While the Kentucky Derby has no formal dressing guidelines, it is expected that men and women are prepared to look their best, hats included!
  • Hats are expensive. Unless you have the cash to spend or plan on wearing your hat multiple times, don't feel the need to splurge on a professional milliner to design a work of art. 
    • In your search for that perfect hat that is equal parts appropriate and over-the-top, have a budget prepared before you start shopping! Hats are expensive--the millinery profession is no joke and those experts work extremely hard to provide meticulous and scrupulous detail. Some women like to reach out to our friends across the pond for a hand-made design that fits the criteria and vision they have in mind for a hat. Others like to bargain hunt for anything less than $20. In my case, I think there's a sweet spot somewhere in between! Amazon has an extensive selection and hard to beat prices, while Etsy offers more elaborate designs at slightly higher prices, but most hats remain under $100. 
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If you're beginning with your outfit, here are a few pointers:

  • Monochromatic looks (like mine in this post) are a great way to make a statement.
    • Monochromatic looks are not everyone's thing, but I think it is the first step in creating a truly chic look that turns heads. From your hat to your heels, I recommend blending hues of the same color throughout your outfit. This way, once your ensemble is together, it won't be impossible to find a hat in just the right shade of periwinkle...
  • Dress for your seats (inside/outside).
    • As I mentioned above when considering your style of hat, deciding whether or not to sport chic pants, or spaghetti straps, consider where your seats are. If you are not in the covered mezzanine section or inside the boxes, I recommend a strapless look for those that don't burn easily and capped sleeves for those that do. Long sleeves are a no! The day is sure to be hot, and how can you enjoy the wonderful day if you're miserable in what you're wearing?
  •  Dress for the long day ahead.
    • While it is usually guaranteed to be hot, I've seen my fair share of rain-soaked Derby weekends. Check the weather and dress accordingly! Bring plenty of sunscreen with you, even if you don't have open air seating or are in the center field. Likewise, if you aren't 100% comfortable in your ensemble, you won't be able to enjoy the day. The races begin around 8 or 9 AM and go non-stop until around 5:30-6 PM when the actual Derby race begins. Until then, smaller races are happening all throughout the day. You will be there all day long so bring a pair of flats or sandals in your handbag to change into. The wait is well worth it though, I promise! 
  • Try out runway styles
    • It's time to consult your Pinterest fashion board for those dreamy runway looks you feel like you could never wear in your day to day routine. The Kentucky Derby is a pinnacle of your fashion career! All gates are open (pun intended), and there are no rules. Now is the time to try out that daring style, or experiment with different items in your closet. The fancy-factor is at a all-time high at Churchill Downs, so this is one occasion you never have to worry about being overdressed. 

Shop Fascinators 

Shop hats

That's not all! Stay tuned for  P A R T  T W O  of my Derby guide on the blog! 

. . . . . 

Next up: dressing like a million bucks for next to nothing at the races & racing etiquette and best practices ... 

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Obviously, 

Olive