When it comes to emotionally charged characters in Chicago P.D., few compare to Detective Hailey Upton. Played by the immensely talented Tracy Spiridakos, Upton has become one of the show’s most compelling figures—tough as nails, fiercely loyal, and constantly wrestling with inner turmoil. So when fans were left heartbroken by the unraveling of her relationship with Jay Halstead (portrayed by Jesse Lee Soffer), there was one thing we never got to see: Hailey’s wedding dress.
But now, thanks to an exclusive reveal from the show’s costume designer, fans finally have a glimpse into what could have been. And it’s more beautiful—and more symbolic—than anyone could have imagined.
Upton and Halstead’s relationship, affectionately dubbed “Upstead” by fans, was one of the emotional anchors of the series. Their bond was forged in trauma, trust, and time spent in the trenches of Chicago’s most dangerous neighborhoods. So when they secretly tied the knot in Season 9, it was a quiet but meaningful moment—no lavish ceremony, no flowing gown. Just a simple, courthouse union.
What makes this never-worn dress even more poignant is a tiny detail only Hailey (and eagle-eyed fans) would have noticed—a small blue stitch sewn into the inner hem, representing the traditional “something blue.” “It was a nod to Jay,” Kaufmann revealed. “Blue is often associated with loyalty and trust, both of which defined their relationship. Even though the wedding was never meant to be traditional, that one hidden detail gave it meaning.”
So if the dress was conceptually ready, why didn’t we ever get to see it? “It all came down to narrative,” Kaufmann said. “The writers decided that a quiet, private ceremony was more fitting for Upstead. And later, when the storyline pivoted toward Jay’s departure, it didn’t make sense to include the full wedding visuals.” Still, the design team kept the sketches—and now they’re giving fans the closure they never knew they needed.
Since the reveal, Chicago P.D. fans have taken to social media to share their thoughts on the design, and the consensus is clear: it’s perfect. “This is EXACTLY the dress Hailey would wear,” one fan tweeted. “Classy, strong, no-nonsense but still beautiful.” Another fan wrote, “I’m crying over a dress that doesn’t even exist. This is the emotional damage Chicago P.D. has done to me.” Some even expressed hope that the dress could make a surprise appearance in the future—perhaps in a flashback or dream sequence. With Chicago P.D., anything is possible.
More than just an outfit, Hailey Upton’s imagined wedding dress is a metaphor for her character arc. She’s not showy, but she’s strong. Not flashy, but full of depth. She leads with logic but carries heartbreak beneath the surface. The design says everything about who Hailey is: a woman shaped by pain, but still capable of love. A woman who wears her emotional armor but allows small, meaningful details to slip through. A woman whose quiet resilience makes her unforgettable.
While fans never got to see Hailey Upton walk down the aisle in that breathtaking dress, the reveal by the costume team gives us a touching glimpse of what could have been. It’s a reminder that even in stories unfinished, beauty lives in the details—and sometimes, in the designs we never got to see. One day, maybe Hailey will find her moment again. And if she does, we’ll be waiting—ready to see her finally get the wedding she deserves. Until then, the dress remains a beautiful “what if” in Chicago P.D. history—a piece of unspoken storytelling that lives just outside the frame, in the hearts of fans who never stop hoping.
