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The Dress Spot: Improving Online Retail for Women’s Apparel

The typical search experience isn’t necessarily what’s going to hit it out of the park for women shopping online.

Two years ago, Jeremy Penrod, the founder of The Dress Spot, watched his fiancé, Sierra, struggle to find the right dresses for her seven bridesmaids to wear on their wedding day. She was looking for slate blue dresses to match the couple’s wedding colors. Despite her best efforts, Sierra Penrod soon learned her task was impossible. She couldn’t find seven slate blue dresses that were all in the same style and the right size for each bridesmaid.

“We ended up changing the wedding colors because she couldn’t find the dresses,” said Jeremy Penrod. “There was a lot of drama because of it. People were crying. It was really traumatic.”

As he watched this scene unfold, Jeremy Penrod saw an opportunity. Maybe it was a grand romantic gesture, or maybe it was just this young programmer’s entrepreneurial mind at play. (It was likely a combination of the two, but it definitely wouldn’t hurt Jeremy’s professional or personal life if he played up the romantic side of the story a bit more.) Whatever the case may be, the idea for The Dress Spot emerged as his fiancé was living a bride’s nightmare.

“I was just like, jeez, these girls are ready to spend over $100 for a dress and no one is able to put one in front of them,” said Jeremy Penrod.

In a move that seems only fitting (dress shopping pun — nailed it!), Jeremy Penrod partnered with his best man, Craig Nordstrom, to co-found the new startup.

“I never saw myself doing dresses ever, ever,” Nordstrom told The Daily Herald last August. “I am not a fashion guy. I was thinking how did I get myself roped into this, but then I saw the potential.”

What do these two guys know about dresses?

“Very little,” said Jeremy Penrod. “I didn’t really know anything, and that’s actually been a challenge for the startup.”

A challenge Sierra Penrod has helped The Dress Spot overcome.

“She was very pivotal in the creative process — coming up with a lot of the design,” said Jeremy Penrod. “I would create a mock-up or a prototype, send it to her, and then she’d rip it apart and say what she liked and what she didn’t like.”

The couple repeated that process dozens of times until they eventually ended up with something Sierra Penrod loved. At that point, they put their product in front of other people and made even more changes.

Sierra Penrod is currently teaching English at Timpview High School, but she still gives her input, especially when it relates to the user experience and user interface aspect of the website.

“We’re kind of conditioned to feel like we can find anything within seconds online. But when it comes to women’s apparel, if you have any sort of criteria of what you’re looking for, it can actually take a very long time,” said Jeremy Penrod.

He believes designing a user interface for women is different than designing for men.

“The typical search experience isn’t necessarily what’s going to hit it out of the park for women shopping online,” said Jeremy Penrod. “At the same time, Pinterest, and other very female-oriented experiences, are not retail experiences. Your average online shopper is trained to treat sites like Pinterest not as a retail buying experience, but as an inspiration searching experience. They sort of turn off the purchasing part of their impulses. It’s a very interesting psychological difference.”

The Dress Spot has developed a very sophisticated image recognition and search technology in order to accurately portray the true colors of the dresses they promote on their site. They partner with brands — Macy’s, Dorothy Perkins, Forever 21, Tommy Hilfiger, and Nordstrom, to name a few — who give them access to their inventory (images, descriptions, pricing, and other valuable information) using a product feed. The Dress Spot then performs their own special tagging to figure out things like whether a dress has a cap sleeve.

“The most important part is we perform an image analysis on the image itself to extract the true color of the dress,” said Jeremy Penrod. “So it’s not just blue, red, or black. It’s sky blue, or late blue. It’s several different shades of blue. It’s very, very specific. That image analysis is performed and then we let people search through all of these inventories by ultra-specific criteria.”

The company is still trying to figure out its revenue model, but as of now they’re working with affiliate networks who track the analytics for the brands. Whenever a sale originates from TheDressSpot.com, they receive a commission. The company currently doesn’t handle any transactions on their own site, but Jeremy Penrod said that may change in the future.

“Everything is on the table. We’re a very small, lean startup. We’re constantly experimenting, and different revenue streams are constantly being talked about,” said Jeremy Penrod.

The first step for the company is to try to turn themselves into a channel brands are excited to leverage and be associated with. With that comes higher commissions and more opportunities.

“The problem we’re solving is online apparel search is old. It’s like 10 years old or older. Retail search for non-apparel items is typically really good, but when it comes to someone looking for a light blue, floor length gown for their daughter’s wedding, women will spend weeks — and they have to, there’s just no easy way,” said Jeremy Penrod.

It’s something Jeremy and Sierra Penrod experienced firsthand. They’re now doing everything they can to help women focus more on their life-changing event, and less on the challenge of finding the right dress, in exactly the right color and size, for everyone who’s attending.

It’s kind of romantic, don’t you think?

Published 1/2/2014