What to Wear to the Preakness

Here’s some fashion inspiration on how to dress to stand out for that unique horse racing event like the Preakness. Providing some helpful tips to make sure your outfit impresses from the starting gate down to the final stretch.

This is a sponsored post with America’s Best Racing. As always, my reviews remain honest, and all opinions are my own.

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All photos by Vernon Davis of VSDavis Photography.  This Maryland-based photojournalist specializes in portraits, weddings, and street photography. You can follow him on Instagram @vsdavisphotography or his website.

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I’ve been invited to the Preakness happening this Saturday. I’m looking forward to attending and seeing all the different people wearing the latest fashion, especially when it comes to fancy headpieces! 

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The Preakness, which is the second jewel of the Triple Crown, will be held in Pimlico Race Course located in Baltimore, Maryland.  Did you know that the Preakness has been
around since 1873 (Kentucky Derby started in 1875, and Belmont Stakes began in 1867)
and was named after the horse that won the Dinner Party Stakes in 1870?

Thanks to America’s Best Racing, I have the opportunity to attend my first horse racing event!  America’s Best Racing is a source for those interested in learning more about the sport of Thoroughbred horse racing events in North America.  The main focus of the platform is on the sport’s lifestyle and competition.  It was created and funded by the Jockey Club.  If you will be in town for the Preakness and new to the Baltimore area, here’s an article they featured on food and drink guide to the city.

OK, I’ll stop horse-ing around (pun intended) and get to the point of this blog post.  Let’s talk about what to wear to horse racing events such as the Preakness (or Belmont or Kentucky Derby).

  • Spring dresses, blazers, jumpsuits are among the favorites.  Depending on your hat or fascinator, you might want to keep this simple and let the hat be the highlight of your outfit.  Keep an eye on the weather in case of rain and don’t forget to pack that poncho (FYI – umbrellas are not allowed for the Preakness)
  • We know the hats are really the standout accessory for this event!  Unless you live in England, where you might be able to wear it to more than one occasion, this is the time to showcase that fascinator you’ve been eyeing.  Go big, bold, or colorful; this is the time to wear it proudly
  • As for shoes, keep in mind the grounds might be a little difficult to walk around, so consider wearing wedges or block heels as opposed to stilettos.  Bring comfortable back-up shoes since this is an all-day event.  In case of rain, pack a pair of rain boots for safe keeping
  • Jewelry can be kept simple (or even omitted) especially if you have that showstopping fascinator or hat on display
  • Find a clutch or small over the shoulder bag that matches your outfit perfectly.  You can also put that small bag inside a bigger bag (for Preakness, it can’t be bigger than 18×18) to carry sunblock, change of shoes, extra phone chargers, and any other essentials

I’ve put together a few looks for inspiration from my recent
visit to Misty Manor in Marriottsville.

Maxi Dress

Beautifully colored in red with tropical print, this maxi dress has tiers of ruffles that add flowing movement.  Pair with modern elegance of a chunky heel.  Finish with a simple fascinator for that touch of elegance.

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Shop This Look



Wrap Dress

Simple elegance goes a long way such as this lovely blue and white polka dot wrap dress with hi-low ruffled hem. Finish off with a fascinator or hat.

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Shop This Look

The fascinator in the picture is sold out, but I have linked similar items



Off -The-Shoulder Dress

Want to look extra special? The floral lace adds rich depth to this off-the-shoulder dress. Wear this wide brim hat and chunky heels as the perfect pair to complete the look. 

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Shop This Look

I’ve linked additional hats as well



Special thanks again to America’s Best Racing for this fantastic opportunity

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