Three questions with Cynthia Rowley

On a cold Monday evening last week at the Sony Hall in NYC, a lineup of women comedians gathered to do stand-up on stage.

But the women were there to show off more than their comedy skills. Away from the typical Spring Studios venue that hosts the majority of New York Fashion Week, the occasion was actually Cynthia Rowley’s Fall/Winter 2023 show.

After hosting a few comedy nights at her Montauk, New York, store last summer, the designer sought the help of her friends from Saturday Night Live, among others, to curate her fashion stand-up and present her latest collection.

On stage were seven comedians, including Rachel Feinstein and Nikki Glasser, dressed in Rowley’s creations, who also did mini comedy routines. “People are like, ‘Why did you do stand-up comedians?’ And I said, if it’s not a 50-50 chance it’ll be epic or the end of my career, why bother?” Rowley told Retail Brew after the show.

We spoke to Rowley about the motivation behind showcasing her designs as part of a comedy show, her evolving customer base, and adopting new retail strategies. And she had some insightful takes.

This interview has been lightly edited for length and clarity.

Why did you pick a comedy show concept for your fashion week presentation?

Every time we have a show, I say, “Well, guys, I hope you enjoyed it, because it’s never gonna happen again.’ And the next week, I’m like, “Where are we going to show?”…It’s really a lot of work. But in September, we do a more traditional runway show because we show outside, and we invite the public as well as guests. So that is more people at those shows…and then in February, it’s a little more intimate and has to be indoors. So that’s where we try to experiment with a different form of entertainment. There’s two things in fashion: It’s the product, and then the spectacle. I think designers go into the industry with two different points of view. And a lot of designers do create spectacle with the product. It’s entertaining, but harder to monetize—or harder to relate to, maybe—for an audience. So my way of thinking about it is to create the clothes that people want, but then entertain our audience with something that is a spectacle, but that includes the clothes.

Who is the new Cynthia Rowley customer?

It’s really interesting, because it’s evolved immensely. We started a whole new strategy, a whole new way of working. During the pandemic, we knew we weren’t going to show collections, where you present a whole thing and then you ship [it] six months later. I just never really believed in that idea anyway. So we started shipping every week, multiple times per week, doing smaller quantities, selling out, and then either reinventing, reimagining, [or] replenishing the really classic ones. It’s brought a whole new audience or our audiences have gotten younger. It’s very intergenerational now. It’s really, really fun. I think you can see there’s joy. We work with a lot of color. We do all our own original artwork for the prints. We continue with all our surf stuff, but we’ve added a little bit of home. And when more categories come…we’re trying to open more stores, just because it’s a great touchpoint for people now that we’ve really grown our DTC audience. It’s great to pop in and have people be able to experience the brick-and-mortar experience as well.

Why the shift to DTC?

We really just doubled down on our e-comm. We shoot new things every few weeks for the site. And again—the same as [the] shipping cadence—where we design and ship within two to three months. And it’s really a lot of work. It’s really a hustle. It’s like running in front of a moving train. But it makes it really exciting. I think it’s less of a singular vision. It’s a singular vision, through the filter, but we’re able to experiment with new ideas much more easily. But we don’t have a better way of listening to our audience. We really have data and all the analytics, the social media—and that’s been really helpful.—JS