Ten Dresses That Are Perfect for the Preakness Stakes

Events / Travel
Fans at Pimlico on Preakness day. (Eclipse Sportswire)

Walk around Pimlico Race Course on Preakness Stakes day and you’ll learn something about Maryland race fans: They love their state colors — and they dress to prove it. 

Everywhere you look, locals will be decked out in the colors of their state flag: yellow, black and red. Similarly, the state flower, the Black-eyed Susan, is well represented on hats, scarves and novelty ties. 

To help you pick out the perfect Preakness ensemble, we’ve pulled together 10 looks that are perfectly color-coordinated for the historic Maryland track. 

Everything here was selected for style and function during a day at the track. The hemlines are long enough so your legs won’t stick to your seat. And the shoes are wedge heels or flats – because when you’re walking back-and-forth to the betting windows all day, you need speed and comfort.  

Similarly, while ostentatious hats may now define the Kentucky Derby, at the Preakness Stakes, wide-brim hats serve a real purpose: They providing a bit of shade on what can be a scorchingly sunny, hot day.

Of course, to really fit in with the Maryland crowd, you’ll want to add some DYI detail. Creative and thrifty Marylanders are currently hard at work – glue guns in hand – embellishing their hats with yellow ribbons, Black-eyed Susans and even tiny horses. 

With so much state-color enthusiasm in the crowd, it’s practically unsporting to show up wearing anything else. So here is some inspiration in yellow, black and red to set you up for a perfect Preakness Day.

As an added bonus, all 10 looks are inspired by prior winners of the Preakness Stakes, the second jewel of the Triple Crown.

1. Faultless

This simple yellow sheath dress, worn with a wide-brim red hat and delicate accessories, is so flawless, it’s worthy of a tribute to Faultless, the 1947 Preakness winner.

Preakness 1


Maggy London dress


J.Crew j crew earrings
$53 - jcrew.com


Banana Republic red scarve


2. Whirlaway

You’d be twirling all over Pimlico in this full-skirted dress — plus a glamorous hat worthy of a film star circa 1941, the year that Whirlaway swept the Triple Crown.

Preakness 2


Sleeveless dress


Eugenia Kim hat


Forzieri silk scarve


3. Bold Ruler

With stripes this wide and a hat this red, prepare to have your photo taken. You’re going to boldly rule Instagram – in honor of 1957 winner Bold Ruler.

Preakness 3


Heart bangle


Gucci rosebud hat


4. Red Bullet

Not everyone feels comfortable wearing yellow. So a swingy red dress, topped with a jaunty men’s hat, is a solid option. Hint: Tell everyone you’re a one-woman tribute to Red Bullet, the Preakness winner in 2000.

Preakness 4


Ann Taylor red dress


Lands' End wedge shoes


Hermès hermes scarve


Gucci straw hat
$205 - gucci.com


5. Pleasant Colony

Preakness Day is long. Baltimore is hot. This flowing summer dress will keep you cool and comfortable – as if you’re relaxing in a Pleasant Colony, which happens to be the name of the 1981 winner.

Preakness 5

6. Summer Squall

A totally feminine look, this charming floral print and chunky red necklace is going to kick up a storm the likes of a Summer Squall, who won the Preakness in 1990.

Preakness 6

7. I’ll Have Another

With a short, casual dress and an easy pair of flats, you’re ready to rock out in the Pimlico infield – where plenty of people will be saying “I’ll Have Another,” the name of the 2012 winner!

Preakness 7

8. Tabasco Cat

Hope they like some spice in the clubhouse: Though tempered with some mellow yellow accessories, this red dress is hot – as sizzling as Tabasco Cat, who blazed to Preakness glory in 1994.

Preakness 8

9. Charismatic

The little print flowers on this full-skirt dress are a tiny detail, but on Preakness Day, they let everyone know you are in Black-eyed Susan country – and that you’re Charismatic, just like the 1999 victor.

Preakness 9

10. American Pharoah

With a simple sheath dress, this ensemble is sleek and charming – much like the 2015 winner American Pharaoh, who went on to win the first Triple Crown since 1978. A classy look in honor of a classic winner.

Preakness 10

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