15 Stylish Ladies' Outfits to Wear to Preakness Stakes

By Liz Flynn Jun 18, 2024

Preakness Stakes is at the Pimlico Race Course in Baltimore, Maryland, on Armed Forces Day every year. While the Kentucky Derby kicks off the Triple Crown with its formal derby hats and sundresses, Preakness is known for its party atmosphere and adventurous dress code.

Preakness Stakes is the second leg of the Triple Crown, making it an exhilarating event full of high stakes and even higher fashion.

Preakness is a major event where racing fans go to see and be seen. Planning the perfect race day outfit is of utmost importance. After all, you don’t want to show up wearing the wrong thing to one of the most fashionable events on the East Coast.

Have no fear. We have the best tips and outfit ideas for what to wear to Preakness Stakes.

Get ready to shine in first place with these 15 stylish outfit ideas and tips for Preakness Stakes this year.

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Preakness Stakes Dress Code

Preakness Stakes was first run in 1873 and remains the second-most popular racing event in the United States. It is a huge event where people want to dress to impress.

Although Preakness does not have an official dress code on its website, there is an unspoken dress code that most people follow. Preppy, bright outfits are the norm for this lively event.

Men are encouraged to wear khakis, pastel polos, boater hats, and other summery attire. Women can’t go wrong with sundresses, floppy hats, and a Southern chic aesthetic.

Basically, dress with a preppy edge that would work well for a garden party if you want to turn heads at Preakness.

Dress for the Weather

May weather in Baltimore can be unpredictable. The weather can be incredibly hot or mildly cool, depending on the year. Check the weather forecast before planning your outfit.

It’s also a good idea to plan layers or a backup outfit because the weather is getting more unpredictable as the years go on. Just in case, have a lightweight blazer or an umbrella ready in your closet.

A Fitted Cocktail Dress

When dressing for Preakness Stakes, you can’t go wrong with a fitted cocktail dress.

This outfit is classic, elegant, and timeless. You can wear anything from a patterned knee-length cocktail dress to a shorter pastel dress with wedge heels. Accessorize with a showstopping derby hat, and you’re set for a day at the races.

Check out our selection of the best cocktail dresses for any occasion.

A Flashy Fascinator

15 Stylish Ladies' Outfits to Wear to Preakness Stakes

While horse race enthusiasts love to wear giant hats to the Kentucky Derby, Preakness Stakes is a little more flexible.

You can wear a small, playful fascinator with your race day outfit as a fun way to incorporate a garden party vibe.

Match your fascinator with your dress, or play with contrast by adorning your head with a unique work of art made by a local milliner.

Explore more outfit ideas with our guide to race day women’s fashion.

A Mod Dress or Pantsuit

Play with patterns and streamlined silhouettes by wearing a mod dress or pantsuit.

Peter Pan collars, geometric prints, and cropped hemlines are all a must when doing this look. Wear a tailored checkered pantsuit with round-toe heels and Jackie O sunglasses, or turn heads in a simple babydoll dress.

Check out more ideas on how to dress like the ‘60s if you’re looking for more fashion inspiration.

An A-Line Skirt & Delicate Blouse

An A-line skirt and delicate blouse are perfect for a day spent at the races. This look is preppy and feminine. It also looks great with any kind of creative hat.

Wear a pastel or floral skirt with a neutral blouse, or take a walk on the wild side by mixing bright colors and patterns.

Explore our selection of sustainable midi skirts that are easy to accessorize with a delicate blouse.

A Polka Dot Dress

A classic polka dot dress is a must-have for any woman’s wardrobe. Wear an elegant polka dot dress to Preakness Stakes for a timeless look with a fashionable European vibe.

Polka dots work with just about any dress shape. From wrap dresses to maxi gowns, a black-and-white polka dot print always looks good.

Complete your look with a wide-brim sunhat and black sunglasses for the perfect Baltimore summer look.

A Showstopping Hat

Although most people associate the Kentucky Derby with showstopping hats, Preakness Stakes is host to tons of creative millinery.

Turn heads and make a statement with a bold hat. You can wear a larger-than-life sunhat or an artistic fascinator. Whatever you choose, make sure it has an artistic flair that matches your Preakness outfit.

A Wide-Brim Hat & Colorful Coat

Wear a colorful coat and a wide-brim hat if the weather is rainy and cold during Preakness.

A colorful, bold coat livens the atmosphere, even if the event is cold and dreary. Complete your look with closed-toe boots and a sturdy umbrella if needed.

Explore our selection of lightweight trench coats that work for all types of weather.

A Classic Sundress

A classic sundress is one of the best outfit options for Preakness Stakes. This look is effortless and looks fantastic on everyone.

You can get creative with this look, from delicate floral patterns to unique silhouettes and cuts. Wear chunky heels or designer sneakers that can withstand the grass and mud.

Shop our selection of US-made sundresses that won’t break the bank.

A Backless Dress or Blouse

Add an element of surprise to your Preakness outfit with a backless dress or blouse.

This surprise silhouette adds a touch of sensuality to your preppy look. Wear a backless blouse with a flared A-line skirt, or mix modern and vintage with a backless floral boho dress.

An Elegant Jumpsuit

Women aren’t required to wear dresses to Preakness Stakes. You can think outside of the box with an elegant jumpsuit.

Wear a pastel or colorful jumpsuit with a floppy sunhat for a simple yet elegant summer look. You can also make a bold statement by wearing a patterned jumpsuit and high heels.

Don’t miss our selection of organic cotton jumpsuits.

A Sheath Dress & Pearls

Preakness Stakes is the perfect opportunity to dress like a Southern belle. Wear a simple sheath dress and a strand of pearls for an elegant look.

You can’t go wrong with this outfit formula, especially when it comes to a day at the races. This look plays it safe while keeping tradition alive.

Explore more options with our selection of affordable elegant dresses for special occasions.

A Vegan Silk Blouse & Tailored Pants

Be understated and elegant in a vegan silk blouse and tailored dress pants.

This look is a little business casual with a dash of coastal grandma vibes. Tailored pants are a comfortable option for a day outside on the stands. The delicate fibers of vegan silk add a feminine touch to any outfit.

Learn how satin can be an affordable, vegan alternative to traditional silk blouses.

What Kind of Shoes are Best for Preakness Stakes?

Preakness Stakes involves a lot of walking and standing on grass. In addition, the possibility of rain promises the potential for mud. Make sure your shoes are comfortable, sturdy, and waterproof.

Chunky heels, espadrilles, and comfortable sandals are just a few of the best shoe options for Preakness Stakes. Wear shoes that won’t sink into the grass or risk a twisted ankle.

Thankfully, plenty of shoe styles, such as wedge sandals, boots, and fashionable, waterproof sneakers, provide support.

Shop our selection of the best vegan sandals and heels.

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About the Author: Liz Flynn

Liz Flynn is a freelance writer, fiber artist, and amateur art historian. She is passionate about making sustainable, ethical fashion accessible to everyone. In her spare time, Liz can be found crocheting, reading, hiking, or hanging out with her beloved dog, Atwood. She holds a bachelor’s degree in Art History and Education from UC Riverside.

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