What to Wear to a Horse Race | Style Files | Preakness Edit

What to Wear to a Horse Race
What to Wear to a Horse Race

FAVORITE BALTIMORE WEEKEND

For over the past ten years the third weekend in May has been my most favorite weekend in Baltimore! It’s when our city shines for the Running of the Preakness Stakes. Normally thousands of Baltimoreans and guests would have spent the past several weeks determining what to wear to a horse race. Because unless you are running a horse the most important thing about attending a horse race is your outfit! And maybe how much money you are willing to gamble. Due to the coronavirus the Triple Crown races are being rescheduled to the fall. The Kentucky Derby has already been rescheduled for September 5th and we are still waiting to hear the Preakness and Belmont dates.

In honor of my favorite Baltimore weekend I decided this week’s Style Files should be all about deciding what to wear to a horse race. Whether you are attending for the first time or frequent attendee these tips will help you select a show stopping look!

HEADWEAR

If there is one absolute about your ensemble it is that you 100% need a headpiece! Typically headpieces are “derby” hats or fascinators for women and fedoras for men. Each can range is size from small and petite to extremely oversized. Trust me you will see it all at the races! Depending on your budget and effort level there are several options to obtaining a horse race worthy headpiece. My first recommendation is to work with a professional milliner. For the past 4-5 years I have been working with Kentucky based milliner Nicole from Finchy Baby Hats. She offers pre-made hats and fascinators in her Etsy shop or she can create something custom to compliment your outfit. You can also purchase ready made headpieces through Etsy and retailers such as Nordstrom or Amazon.

THE DRESS

When it comes to selecting your outfit think elegance and sophistication. About 85% of women attending the races are wearing a dress. I recommend a mini or midi dress since you will most likely be walking a good bit and possibly on non ideal grounds for a maxi dress. Your dress selection could be bright and bold or something more subtle like pastels and florals. If dresses are simply not your style opt for a modern jumpsuit or pants suit. I styled one below for an example.

Purchasing an outfit, headpiece, possibly shoes, clutch, jewelry and more can easily add up! You’ll find you can certainly spend a significant amount of money pulling your look together but you can also show up super stylish on a budget! In 2016 I won first place as the Most Elegant Lady at Preakness wearing a $60 two-piece set!

WHICH COMES FIRST

It’s like the age old question which comes first the chicken or the egg… or in this case the headpiece or the dress. Of course there is no right or wrong answer. If you fall in love with a headpiece then start with that and find an outfit to match. Or if you choose your look first find a milliner to create a custom headpiece specifically for your outfit. The latter is my personal preference. Each year I start with my dress and Nicole creates a masterpiece based on what I am wearing. Before I worked with Nicole I would select my dress and then purchase a pre-made headpiece to match.

Are you ready to head to the next horse race yet? It’s definitely a bucket list worthy event! Below are six styled outfits perfect for attending a horse race in style! Bonus all the items styled below are currently available.

Now is a great time to start thinking about what to wear for the fall races. Mostly because there are so many sales but selecting your look now reduces the likely hood of someone else showing up in the same dress you are wearing!

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