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Planner Holly Gray at an event.
Photo: Jenn Emerling

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You Go to 30 Weddings a Year — What Do You Wear?

Wedding planners break down their special day style.

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In 2001’s iconic film The Wedding Planner, the titular nuptial organizer Mary (Jennifer Lopez) innocently crosses the street when her high heel gets stuck in a manhole cover — just as a dumpster gets loose and rolls down the hill, careening wildly towards her. In the nick of time, handsome pediatrician Matthew McConaughey pushes her out of the way, saving her shoe and her life, as she points out in that order. Real-life event planners find this scenario absurd — nobody wears stilettos.

“As much as I love the look and I would love to have the J. Lo movie be what we look like in real life, it’s just not possible,” says Renee Dalo of Moxie Bright Events in Los Angeles. “I can't wreck my feet one Saturday, because the next Saturday I'm gonna be doing this again.”

Planner Amanda Douglas with bride and groom.
Photo: A Moving Pictures Studio

Holly Gray, owner of Events by Holly Gray in Los Angeles and a planner with a signature colorful style, echoes this preference for comfortable shoes: “Never heels. Flats all the way.” For Gray, good shoes on their own aren’t enough — she wears insoles, and changes her shoes and insoles frequently, “so that my feet don't get used to them.”

Even the few occasional heel-wearers, like Amanda Douglas of Amanda Douglas Events in Winnipeg and Ellen Kostman of Sidekick Events in New York, stress the importance of a functional shoe. Kostman’s preferred Louboutins are “maybe a two-inch heel — I'm not a six-inch heel, or even a four-inch heel, type of girl.” By the end of the night she’s wearing Birkenstocks. Douglas mostly prefers flats and black Mary Janes from an unexpected brand (“Yes, they’re Crocs,” she laughs). “I don't bust out those heels for just any wedding,” she explains. But she will give herself a couple of inches if it “absolutely feels right.”

But for winter weddings, the Canadian planner’s shoe choice is sometimes limited: snow boots are necessary for running in and out of the venue — and they make dressing up a little more complicated. Douglas’s preferred cold-weather outfit is a floor-length black formal dress. “It’s got this really beautiful lace underlay on the top that's kind of a gray color, and it's got this really beautiful, almost ribbing pattern to it that makes it more interesting,” she says, “But I can hide things under it really well.” Douglas can conceal her boots and the Spanx, body suits, and even long johns she relies on to stay warm at chilly winter weddings.

Both Kostman and her team wear all-black suits — which can get a little hot in the summer. “I've had situations where we were doing outdoor weddings in the Hamptons and it's 100 degrees outside and we're still all in black,” she says. “But what I do say is wear a shirt that when you take your jacket off, you still look professional.” That said, suit pants — not a skirt, certainly not shorts — are non-negotiable. “We do a lot of heavy lifting and bending,” she explains. “If you have to bend over and you're in a dress, you don't want to embarrass yourself or any guests.”

Planner Joe St. Cyr with his team.
Photo: Craig Paulson

Not every planner insists on pants. Dalo, for one, prefers dresses. “I know a lot of wedding planners who disagree with me like, ‘You can't do anything in a dress,’” she says. “Well, I'm wearing Spanx under it, so it's not like I'm gonna show anyone anything. I'm fully Spanxed from head to toe.”

But, like the slacks-sporting Sidekicks, the Moxie Bright planners do have a standard outfit. Of the coordinating eShakti dresses her team wears, Dalo explains, “I don't want anyone to worry. ‘Is my dress red enough? Does this dress not look good on me? Does this dress not fit?’ It's just like, put it on and go. We have things to do.”

Joe St. Cyr, who brings a refined style to his Joseph Todd Events in New York City, doesn’t have a uniform for his team, but he does have a go-to outfit for himself. He prefers a J.Crew suit — “always a blue suit” — paired with “either light blue or light blue striped French cuff shirt, a great-looking print or striped tie, and great cuff links.”

Planner Mary Bell (center) with the band Cashmere.
Photo: Cashmere

Mary Bell of Asheville, North Carolina’s Mary Bell Events prefers all black for herself, and always with glasses. “I do typically look a little bit more like a librarian, to be honest. I have long hair and I keep it in a bun. I wear glasses on wedding days as opposed to contacts.” Bell explains that the glasses allow “people to view me more seriously.” She encourages her staff to wear if not all black, similarly understated colors.

But not every planner loves an understated look — or even having a default outfit at all. “I'm a hot pink and polka dots kind of girl,” Gray tells Racked. “I'm not an all black and blazer kind of girl. I really just try to be the best version of myself and display that to the world and it's worked so far.” Gray says that at the 18 to 20 weddings she plans a year, you can find her running around in a colorful dress and a light sweater — and, of course, flats.

“I try and wear a different dress every time.” Douglas says, “I do tend to get photos with my couples so I don't want to always be in the same dress.” As a result, she has quite the collection. “If I color-coded it, I bet you it would look like a rainbow.”

While styles vary, all the planners agree on one thing: they — and their employees — should not stick out too much. “Wedding days are not about me or my team,” Dalo says. “Wedding days are about my clients. We're never the star of the show.”

This principle guides some aspects of each company’s style, and many consider it a pretty good rule of thumb for everyone at a wedding who isn’t a bride or groom. In fact, more than one planner’s metric of appropriate wedding wear is, as Holly Gray says, “something that looks like you are a wedding guest.”

Renee Dalo of Moxie Bright in her eShakti dress (and Totty Belt work belt).
Photo: Juli Frankel

This presents one small problem, though: a planning staff that blends too seamlessly into the event means that they could be mistaken for such, keeping guests from asking them for help. While St. Cyr encourages this anonymity (“No one should know the wedding planner exists. The only person who should know the wedding planner exists is the bride and groom and her parents. That's it”), most planners like to find some way to appear available — but methods vary, and you’d be hard pressed to find a choice that another planner doesn’t disavow.

Some, like Gray, wear name tags: “I read a long time ago that they do something to your brain that makes you feel comfortable because you don't feel like you have to remember somebody's name.” But others are less keen on this addition. “I would prefer to introduce myself to folks and have the communication start that way, and I prefer not to have team members wearing a name tag,” Bell explains. Still others, like Douglas, carry a trademark clipboard (“It’s this nice kind of neutral brown faux-alligator skin, so it kind of blends in. I usually hold it outwards, so you can see my logo at the top, just as a like, ‘Yep, I'm the one’”), which doesn’t work for everyone either. “I’m not a clipboard kind of person,” says Kostman.

For Kostman and her team, lapel flowers do the trick. “Within each wedding or event that we're doing, we pick a color that seems to be a thread within the event, and every single one of my sidekicks wears a matching flower on our lapel.”

Ellen Kostman and her Sidekicks at an event.
Photo: Ira Lippke Studios

Beside the boutonniere, Kostman’s team has another key piece of gear: a fanny pack. (St. Cyr, a friend of Kostman’s, name-checks the pack as a no for him — proving that no one, even friends, agrees on everything when it comes to wedding-planning style.) The reason for the old-school waist purse? Practicality. “We can tuck all of our things in it,” says Kostman. “The timelines, the safety pins, the scissor, and a pen, and some mints and lip gloss. All the little things that we might need as a a little quick fix for the day.” Kostman’s own fanny pack is Prada.

In the end, keeping it functional is the name of the game for every team. “You don't need to be worried if your false eyelash is about to fall off or if your hair isn't holding the curl. Those are not important things on a wedding day,” Bell says. “If you can't focus on your job because of how you look or what you chose to wear, then you need to rethink your wardrobe.”


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