At Three-Sixty Westport, St. Louis Did Not Simply Observe the Derby; It inhabited It
by Grayling Holmes / Photos provided by Three-Sixty Westport and Grayling Holmes
I have never counted myself among the devoted followers of the Kentucky Derby. Like many, I have been content to observe the main event from the comfort of home, appreciating the spectacle from a distance. This year, however, was different. An invitation arrived to the Three-Sixty Westport Kentucky Derby Soirée, and with it came an unspoken understanding: one does not simply attend—one arrives properly.
Preparation, as it turns out, is part of the ritual.
Research quickly revealed that Derby style is its own language—one spoken fluently in color, contrast, and confidence. I ordered accordingly: a traditional fedora and a straw boater, the latter chosen for both form and function, given the well-documented climate of Derby Day. A powder blue blazer emerged from the closet, paired with newly acquired navy slacks—tailored not only to the occasion, but, candidly, to time itself.
The bow tie, however, proved the true test.
A pre-tied version, thoughtfully ordered, failed to arrive. What followed was a forty-five-minute negotiation with YouTube and muscle memory. The instructor, with enviable ease, described the process as simple—before inevitably arriving at the portion he described, somewhat ominously, as “tricky.” He was correct. But persistence, as it often does, prevailed. The result: a properly tied bow, aligned in both structure and spirit.
One dresses not merely for oneself, but for the room.
And the room, as it turned out, delivered.
My companion for the afternoon, Mary, arrived in a study of Derby elegance—her white fascinator poised with architectural precision, her blue-and-white ensemble a balance of restraint and statement. Together, we made our way to Westport Plaza, a destination that has, in recent years, undergone a transformation both deliberate and unmistakable.
Under the stewardship of Lodging Hospitality Management, the property has evolved into something altogether more current—without sacrificing its original sense of occasion. As Chairman and CEO Bob O’Loughlin has noted, the intention has been clear: to elevate Westport into a premier destination for both visitors and the local community. “The entire Westport complex is now home to some impressive offerings including the newly opened Basso Westport and the ever popular Westport Social,” O’Loughlin said,
On this particular afternoon, the vision felt fully realized.
We ascended to the rooftop of the Gold Tower, sharing the elevator with a couple dressed in striking red—a visual declaration that this would not be a subdued affair. When the doors opened, the atmosphere shifted instantly. What awaited was not merely a party, but an interpretation—St. Louis’ answer to the pageantry of Churchill Downs.
And it was convincing.
The details were intentional. Woodford Reserve mint juleps flowed with theatrical abundance, served in traditional pewter cups designed to frost at the touch—both aesthetic and functional. The effect was immediate: a sensory bridge to Louisville, constructed without compromise.
According to Vice President of Sales and Marketing Todd Hotaling, the goal was to create an experience that mirrored the refinement of Derby celebrations without requiring the journey itself. It is a delicate balance—to evoke without imitating—and here, it was achieved with notable precision.
The culinary offerings followed suit. The buffet was expansive, but more importantly, intentional—each dish presented with the kind of care that suggests it was meant to be seen before it was tasted. And yet, it delivered on both fronts.
But if the food was memorable, the crowd was definitive.
This was where St. Louis came to be seen.
The aesthetic directive was clear: arrive as though stepping directly from the infield or the grandstand at Churchill Downs. Women in sculptural hats and flowing silhouettes. Men in straw boaters and Panama hats, many accented with subtle flourishes—a feather here, a ribbon there. It was not costume; it was commitment.
The energy followed naturally.
What Three-Sixty Westport achieved was something more than replication. It was translation—capturing the spirit of an event 266 miles away and rendering it convincingly, elegantly, and with a distinctly local point of view.
For an afternoon, at least, St. Louis did not simply observe the Derby.
It inhabited it.
On Derby Day, one of the crown jewels in the LHM firmament of properties, Three-Sixty Westport, ran for the roses and brought them home.
