When Eleanor Ylvisaker tried on her first custom-made wedding dress, she knew right away: It was all wrong. “It was a beautiful dress,” she says now. “But I had such a specific idea of what I wanted.” So specific, in fact, that Ylvisaker even had her vision sketched out by the design team at Earnest Sewn (the denim brand she helped launch in 2004) before meeting with her chosen dress designer. But something didn’t click. The designer—who Ylvisaker declines to identify—went for rhinestones where Ylvisaker had hoped for something subtler. “I probably didn’t know how to describe what I wanted,” she says in polite hindsight. “But I remember feeling sick.”

The wedding was only a few months away and a do-over dress was not in the budget—until Ylvisaker happened to find herself seated next to Zac Posen at the American Museum of Natural History benefit in NYC later that same week. When Posen heard the bedazzled tale of woe, he insisted Ylvisaker come to him for a new gown. The result, finished in just two months, featured ivory jacquard silk, a drop waist and a vintage lace veil. Although the Posen dress was not exactly a gift, Ylvisaker made the budget work by repurposing the first dress as a rehearsal-dinner gown. “It was everything I wanted and beyond anything I could have imagined,” she says.

Almost a decade later, Ylvisaker, now 37 and a mother of two, is amused by how heartbroken she was about the first dress. But her designer-in-shining-armor story (and the subsequent press generated) may have kicked off what is now considered the ultimate status symbol among brides who work in fashion or reside in certain zip codes: to have your wedding dress custom-created by a designer who ordinarily dresses only the biggest of bold-face names for far more public events. Posen describes it as a “rare luxury available only to those lucky enough to have the funds” and, presumably, the right connections—Posen takes on just a handful of custom wedding dresses per year. Meanwhile Francisco Costa of Calvin Klein has made dresses for several high-profile brides, including furniture designer Ana Meier, daughter of legendary architect Richard Meier, and Paula Bezerra de Mello, director of public relations for the famed Philippe Starck–designed Hotel Fasano Rio de Janeiro.

All designers and brides interviewed declined to comment on exactly what “funds” these dresses require, but high five and even six figures are reportedly not uncommon. Many designers view custom dress projects, however, as a marketing opportunity—for both sides. “A bride becomes an ambassadress of the house and this has turned into a PR tool,” Posen explains. “That’s not why I do it. But having a designer make your dress can also help the bride achieve a certain level of press or status.” Indeed, Ylvisaker considers herself “extremely lucky” to have had a Posen dress “because I was not nearly as high profile as the girls having dresses made for them today.” Still, Posen’s dress rescue mission piqued the interest of Vogue, which covered Ylvisaker’s wedding alongside the nuptials of socialites Plum Sykes and Vanessa von Bismarck.

Not every designer is dying to tie that particular knot. “I’ve only done a couple of wedding dresses for friends and to be honest, I’m a little bit cautious about doing more,” says designer Thakoon Panichgul. “It’s such a big day, and there are a lot of expectations.” A wedding dress, after all, is often the culmination of a fantasy decades in the making, and perhaps especially so for women who work in fashion or who frequent the gala circuit. As Ylvisaker says, “There is so much pressure on that one opportunity to wear the perfect dress.” For a designer, the pressure is doubled, as he works to honor both his own aesthetic vision and the bride’s—who may have standards that make Anna Wintour look laid back.

After all, any bride with the means to commission a custom dress is unlikely to be planning a low-key kind of wedding. When Meier married real estate investor Daniel Creighton at her family home in East Hampton, her 250 guests dined and danced under a clear tent hung with sheer white linen panels, designed by Lewis Miller. “Everything looked simple, classic and effortless, but there was a lot of very complicated planning involved!” says Meier now. And the same could be said of her dress, which Costa designed directly on Meier, draping and sculpting the fabric around her through six fittings. “The construction of my dress was complex and it was fascinating to watch how Francisco would make a tiny change, like tuck the shoulder strap a couple of centimeters and completely change the shape of the bodice,” she says. “But I think sometimes you get dressed up in these white dresses and it’s not necessarily you. At the end of the day, I felt like me.”

That said, control is in no way guaranteed when working with creative genius. Carolyn Tate Angel had her dress designed by Kate and Laura Mulleavy of Rodarte and, even after pulling together inspiration boards of favorite dresses, had to make peace with the Mulleavys’ fabrics. “I’d be like, should we have lace? And they’d say, ‘Let me daydream…I see you in tulle!’” Angel, who was an editor at W at the time, was nevertheless thrilled with the end result: “Working in fashion gave me the ability to design my own dress, but for someone who doesn’t work in fashion, it would be a lot easier to go to Vera Wang, Carolina Herrera or Oscar de la Renta.”

But other brides say that a chance to reject the classic Vera Wang–style wedding atelier experience—not to mention its Kleinfeld spawn—is the whole point. “I actually did go to Kleinfeld at first, more as a joke, and thought, ‘Wow, this solidifies all of my fears,’ ” says Joanna Hillman, the style director at Harper’s Bazaar. She ended up wearing a Rochas dress, which designer Marco Zanini gifted her from his archives. Paula Bezerra de Mello, who was married on the rooftop of the Fasano hotel, also eschewed the “big white dress” moment. “I love lace and tulle as much as the next girl, but that fairy-tale bridal ball gown was never an option,” she says. “I wanted to feel in charge of my dress. Francisco was a genius at empowering that feeling.” Empowerment aside, a big gown may have been more forgiving: “I was happy that I ended up losing enough weight to look good in the dress,” Bezerra de Mello notes. “Those 10 pounds made all the difference.”