The Triple Crown of Prep: The Kentucky Derby, Preakness Stakes & Belmont Stakes

The first leg of the triple crown
The Kentucky Derby, the Preakness & the Belmont Stakes

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The Triple Crown is the preppy sporting event that unfolds over a five-week whirlwind at the start of every summer. So what's all the hype about? At least nominally, the Triple Crown is about horse-racing (and giant hats). Most preppy connoisseurs and laypersons are familiar with at least the basics of the Kentucky Derby, the proverbial "fastest two minutes in sport." But as it turns out, all races are not equal in the Triple Crown, and are actually quite different. In preparation for the 2020 Triple Crown chase, here's a quick rundown of the festivities and culture behind all three races that make them so unique. If you're just here for a dress, a tie, or some derby pants, check out the Derby Collection.

The Kentucky Derby

Kentucky Derby Vineyard Vines

The Kentucky Derby kicks off the season at Churchill Downs. At only two minutes in duration, it's a very long celebration for a very short race. In Louisville, Kentucky (famous home to Churchill Downs), locals and guests celebrate the event on the first Saturday of May each year, starting a two-week-long festival. The Derby is celebrated for its long-lasting traditions, such as the winning thoroughbred being draped with a garland of roses, or sipping on the official drink - the every delicious and refreshing Mint Julep. Of the three Triple Corwn races, this one takes the cake for being the most festive and brigh. You can count on there being an abundance of bright accessories, pastel palettes, and seersucker patterns on attending patrons each year, whether in the infield of box seats.

Since at least the 1960s, it has also been tradition for ladies to sport large and extravagant hats, part southern style, and part spectacle. The style for men lies somewhere between jubilant and classy, with many seersucker suits to be seen on celebrities, and Nantucket Reds on more party-going patrons. And of course, Vineyard Vines boasts its role as the the official Derby style, so look out for foam VV whale hats throughout the crowd!

Preakness Stakes

Preakness fashion Pimlico Race Track

The second race in the series kicks off in Baltimore, Maryland at the Pimlico Race Course on the third Saturday in May. Known as the “middle jewel of the Triple Crown,” it boasts quite different customs than the Derby. For starters, there are no wide-brimmed hats like you’d see at the Derby. At the Preakness Stakes, they trade big hats for small, ornate ones similar to the Royal Family’s. Along with that, women go for bold, bright neons rather than typical preppy patterns like madras or seersucker. Heels are also more common than in Churchill Downs, where many revelers choose Jack Rogers for their shoe. For men, attire greatly depends on seating arrangements. In the Clubhouse, which is pricier and more exclusive, the dress code requires suit or slacks with a sport coat. If you’re living large in this section, many opt for a fun tie or unique belt (expect to see a TON of Smathers & Branson). Another entertaining seating option is the Grandstand, which is slightly more casual but still has great views. Here, you should dress in a light jacket with slacks.  The Infield is a completely different scene, featuring “PreakFest,” a music festival with large standing audiences. Recently, artists such as Armin Van Buren have played house or EDM music, making this a very rowdy experience. Here, shorts and comfortable boat shoes for men are fair game, while the ladies rock casual sundresses and sandals. If you opt for the infield, your rule of thumb should be not to wear anything you wouldn't mind ruining! 

Belmont Stakes

Fashion at the Belmont Stakes

The last, and oldest, of the Triple Crown races are the Belmont Stakes, taking place in Belmont, New York at the start of June. And going with the trend, this is the least whimsical or rowdy of the races. Continuing traditions from their first opening in 1867, the focus is more on the racing than festivities since the Belmont is also the longest of the races.

The Belmont Stakes is famous for its black and white appearance - mirroring their official flowers of red roses, black-eyed susans, and white carnations. Of which, the latter makes up the garland, deeming the race the “Run for Carnations”. Not only is it less ornate, but the crowd is much more intimate than Preakness or the Derby, with attendance at roughly half of its counterparts. In terms of attire, these very classy and understated New Yorker vibes arise in part because of a strict dress code for all guests age twelve and above. For men, in the Paddock and Box, pants and collared shirts are required. In the Grandstand and Clubhouse, shirt and shoes are required, and tank tops and not permitted. Because of this, men tend to be dressed to the nines in suits or nice jackets, with small touches of flair on pocket scarves or socks. Women on the other hand have a very distinct look to follow. Monochrome outfits of black or white are the trend, with pops of red in the forms of shoe, lip, or understated hat. The track is also padded, meaning heels are accommodated and therefore a common choice for ladies' footwear.

Final Thoughts

The Triple Crown! Not as uniform as you might have thought! Each race has its individual cultures and customs, while they vary within themselves a great deal as well. Some may think that the Kentucky Derby is far too wild or gaudy, while others may think the Belmont Stakes are uppity and drab. Each race is unique, but all are more than worth attending. For example, the Derby kicks off a huge celebration, while the final leg at Belmont can make or break if the Crown is won. To win the Triple Crown of Thoroughbred Racing, a horse must win all three races and be three years of age to even compete. To date, only thirteen horses have ever taken the crown.

Whether you attend for the betting, the booze, the styles, or the racing itself, the Triple Crown of horse racing is the original sport to boast a Triple Crown title, and it remains the best!


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