Justin Alexander was not only the designer of both of Tiler’s wedding dresses—he was also in attendance, celebrating the full-circle moment he inadvertently helped create.

For the ceremony, Tiler wore a dramatic ivory gown with off-the-shoulder swags and a sweeping train adorned in three-dimensional rosettes and vines. Pearl beading glinted from the centers of rosebuds and traced the curves of appliquéd leaves. Her hair, parted deep to the side, evoked the silver screen sirens of the 1940s. Completing the look: pearl-encrusted Jimmy Choo sandals with serpentine straps that shimmered as she moved with the control and elegance of a true principal. Roman wore a black Dolce & Gabbana tuxedo for the ceremony, then changed into a white jacket for the reception.

Her second dress, also by Alexander, traded structure for movement: a lace strapless gown with a sweetheart neckline over a soft beige slip. The sheer ivory overlay was embroidered with delicate florals and leafy vines—romantic, ethereal, and, as she put it, “built to dance in.”

The ceremony was deeply personal. Tiler carried a locket with a photo of her late father fastened to her bouquet, and walked down the aisle to his favorite song, played live by their dear friend and violinist Hilary Hahn. “I felt him strongly as I walked,” she says. “I will never forget the way Roman looked at me.” Roman’s vows included memories of the many cross-country trips he took with Tiler to visit her father in his final year—acts of quiet devotion that, in hindsight, revealed the depth of his love. “Even though I feel his love every day,” she says, “I had never heard it articulated like that before.”

Officiated by Reverend Timothy Weisman, the ceremony ended with cheers and kisses, and the couple stepped out into the sunshine. “It was a hot summer day,” Tiler recalls. “Quintessentially New York.”

Planned by longtime friend Claudia Hanlin of the Wedding Library—whom Tiler called “the MVP of our wedding”—the celebration was filled with thoughtful details and warm textures. Claudia sourced everything from hand-painted candles from Ukraine to custom block-printed cushions from India, and collaborated with Marcella Floral Studio on lush, painterly florals. “She knows my taste so well,” Tiler says. “I trusted her completely.”

The tented garden party behind Tavern on the Green struck the right note: elegant, unfussy, and anchored by a sense of place. Tables were layered in printed linens, softly glowing taper candles, and overflowing florals in blush, cream, and green. Escort cards, ceremony programs, and menu cards were all custom-designed by the Wedding Library in collaboration with Bella Figura.