Weddington Way is marrying data with dresses to make weddings less painful

When Ilana Stern was in Stanford Business School, she knew she wanted to start her own online fashion business, and she started thinking about dipping her toe into the wedding industry. So Stern started holding focus groups at her Palo Alto house, inviting women to come by to drink wine and eat cheese, to bring their friends, and to tell her their wedding stories.

Soon, the not-yet-married Stern learned that the conception that she and most other people held regarding bridesmaids dresses — that they’re a way for the bride to inflict torture on her friends — wasn’t exactly the whole story.

“One of the common themes I heard was, brides are saying that picking the bridesmaids dresses was the worst part of the wedding,” she said. “I knew bridesmaids think [the process] sucks. I didn’t know brides did too.”

So Stern took her experience as a buyer for Bloomingdales and launched Weddington Way, a company wants to create a platform for group shopping around bridesmaids dresses and wedding attire, connecting a bride and her friends who might not live in the same physical location, but who want a painless purchase experience.

And maybe, even a pretty dress they would *actually* wear again.

Weddington Way launched in early 2011, and since then, Stern said they’ve shipped over 15,000 dresses, registered half a million brides on the site, and sold merchandise to more than 10,000 wedding parties. The company raised $2.5 million in venture funding in 2011 and is now experiencing a period of growth, getting ready to launch an exclusive line of dresses later this year, and attracting attention as a company changing how people think about wedding attire.

Ilana Stern stands in the offices of Weddington Way in San Francisco.
Ilana Stern stands in the offices of Weddington Way in San Francisco.

I sat down with Stern in the company’s San Francisco office to talk about the state of e-commerce right now and how companies can use technology to change what and how we buy. But we didn’t start off talking e-commerce: We got on the subject of college — she graduated from the University of Pennsylvania in 2005 — and the next thing I know, she’s telling me about her senior thesis in international relations on monetary policy and the spread of globalization. So I had to ask her — how did you end up selling wedding fashion?

Getting to Weddington Way

Stern did an internship at Bloomingdale’s during college, at one point emailing the company’s CEO with her thoughts on the program and landing a meeting with him to discuss how it could be improved. After graduation, she realized she realized it was where she wanted to work, even as her friends were heading for consulting or finance jobs.

“I thought, what if I could do the numbers stuff I really like with a widget I really enjoy? And that widget happened to be fashion?”

So Stern worked at Bloomingdales for three years, where she was one of several people on a team of buyers who were ultimately responsible for the failures or successes of their individual category.

“I learned it’s an extremely gratifying experience to sell physical goods to a customer,” she said. “They tell you pretty quickly if they’re happy — they either buy, or they don’t buy.”

Stern left Bloomingdale’s after three years to go to Stanford Business School, because she knew that retail businesses at the time didn’t have a full grasp of technology’s power, and she thought there was an opportunity to marry the two.

“One thing that drove me to leave was the lack of imagination around technology,” she said. “With traditional retail — and it’s starting to change – but there’s a lack of imagination around what’s possible with technology. I just felt really strongly that technology can be leveraged to create better experiences around fashion.”

Stern spent one of her summers in business school interning at Bonobos, the booming men’s fashion e-commerce company (one of the company’s co-founders later invested in Weddington Way.) The following summer she began working on the company, and it launched in January 2011. Stern raised some seed funding from classmates to get started, and then Weddington Way raised a $2.5 million round from firms including Felicis Ventures, Battery Ventures and Trinity Ventures in 2011.

Why it works

What’s key to Weddington Way is that Stern quickly figured out the common process that most brides go through to plan a wedding (heavily influenced by planning guides on wedding websites like The Knot), and then she structured the entire company around that process to best hook the customers at the right time.

Stern said the average bride will start with a color scheme (often inspired by something she likes or sees on Pinterest), and then the first item she usually looks for are the bridesmaids dresses. Once she has the dresses, she goes on to structure most of the wedding and most of her purchases around that color theme and those dresses. So Stern realized the dresses were key to beginning the process of buying a whole wedding’s worth of merchandise.

“We’ve got this beachhead into the downstream purchases,” she said. The company has now expanded to sell other merchandise like flower girls’ dresses, men’s ties and pocket squares, and other wedding attire, but starting with the bridesmaids dresses was key.

A bride and groom get married with the wedding party in Weddington Way attire. All images from this wedding © melissa mcfadden photography
A bride and groom get married with the wedding party in Weddington Way attire. All images from this wedding © melissa mcfadden photography

But even if the bride knows what she wants, she’s usually not acting alone in her purchase, which is where Weddington Way comes in. The bride might want a particular color or aesthetic, but she has to organize a group of people to select and purchase clothing that fits around it. Which isn’t easy if bridesmaids are scattered across multiple cities and countries and have vastly different body types and fashion preferences.

The company has devised a platform for group shopping — it allows the bride and bridesmaids to all contribute ideas for dresses and colors to a group board, where they can comment and share ideas. The dresses retail for an average of $200, and Stern said she wants them to be fashion-forward but accessible (she said about 75 percent of brides ask the bridesmaids to purchase the dresses themselves). Once the dresses are picked out, the bride can log in to track when everyone has purchased their dress and when those dresses will arrive.

Interestingly, Stern said one of the reasons bridesmaids have historically worn identical dresses is that it was the easiest way to buy them — a bride could buy ten of the same dress and ship them to people, and have them altered to fit. But now, with more sites like Weddington Way or J.Crew offering a single dress in 50 colors and styles, brides are accepting the idea that you can create a unified aesthetic without matching uniforms. Stern said 80 percent of brides that come through Weddington Way have had bridesmaids wearing similar colors, but not necessarily styles, of dresses.

Weddington Way bridesmaids dresses fashion e-commerce Ilana Stern
Bridesmaids dresses in the Weddington Way offices in San Francisco.

Using technology to sell dresses

There are some aspects of selling clothes that are still best done in the centuries-old style of looking at a fabric swatch and feeling the texture between your fingers, and Weddington Way is no different. The company sends out fabric swatches to customers for free, along with handwritten notes, because Stern said holding up a piece of fabric is crucial to knowing what will work.

“It’s about having that tactile experience,” she said.

But there are other ways technology can change how people find the right item. For instance, customers put in all their measurements when they register, so when they order their dress, the company compares the person’s measurements to the measurements of the dress, as well as data on how that dress usually fits customers. The company can automatically flag any orders where the numbers don’t match up, indicating that someone might have bought the wrong size.

And when a bride first registers on the site, entering her name and wedding date, the company will track the colors and styles she’s looking at, and then have a personal stylist contact the bride making suggestions based on that history.

But oddly enough, one problem that Stern found they didn’t need to fix was ship times. Unlike other companies competing with Amazon Prime’s news shipping standards, she said she found that people were ordering dresses so far in advance, adding rush orders to the custom-made dresses wasn’t necessary. Although if someone comes to the company with a last-minute emergency, they’ll figure out a solution.

“We’ve never missed a wedding,” she said.