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Meet The Topshop Alum Who Could Change How You Dress At Work

Whistles CEO Jane Shepherdson is bringing some surprisingly chic wardrobe staples to American women.

  • <p>Zippy Jacket, $575, and Zippy Skirt, $500</p>
  • <p>Audrey Striped Crop Top, $155 (shorts not available at Bloomingdale’s, $155)</p>
  • <p>Audrey Striped Crop Top, $155</p>
  • <p>Daisy Foil Skirt, $195, and Foil Patchwork Vest, $190</p>
  • <p>Lovebird Jumpsuit, $325</p>
  • <p>Verity Large Rucksack, $500</p>
  • <p>Tiger Print Crop Top, $240</p>
  • <p>Tiger Print Culotte, $425</p>
  • 01 /09

    Zippy Jacket, $575, and Zippy Skirt, $500

  • 02 /09

    Audrey Striped Crop Top, $155 (shorts not available at Bloomingdale’s, $155)

  • 03 /09

    Audrey Striped Crop Top, $155

  • 04 /09

    Daisy Foil Skirt, $195, and Foil Patchwork Vest, $190

  • 05 /09

    Lovebird Jumpsuit, $325

  • 06 /09
  • 07 /09

    Verity Large Rucksack, $500

  • 08 /09

    Tiger Print Crop Top, $240

  • 09 /09

    Tiger Print Culotte, $425

The concept of "work clothes" is almost comical in an era when office environments vary so widely from disturbingly casual (your living room couch) to uncomfortably conservative (the oldest old-school firm on Wall Street). Yet people tend to need—and more importantly, want—a specific set of clothes that they wear for work and work only. And women in particular often complain about the lack of wear-to-work options for those who can’t afford Armani suits.

Jane Shepherdson, the CEO of British women’s clothing retailer Whistles, provides such options in the U.K. and is now trying to expand into the U.S.

A protege of Arcadia Group billionaire Sir Philip Green—who owns British stores like Miss Selfridge, Dorothy Perkins, and BHS—Shepherdson worked her way up the company’s steep ladder, landing at the fast-fashion emporium Topshop in the early aughts. She helped transform Topshop into a major shopping destination before departing in 2006. In 2008, she bought a 20% stake in Whistles, a then-middling store in need of a significant revamp, becoming its CEO.

That’s exactly what Shepherdson pulled off: Whistles became the go-to store for polished-but-still-fashion-y separates and dresses for professional women. (Prices—comparable to a Club Monaco or J.Crew—start at $125 for a stripy silk tank, and land at just under $1,000 for a leather jacket. Dresses hover in the $300 range.) With a mix of good design and on-trend ideas, Shepherdson’s Whistles saw 2013 U.K. sales increase by 24%, year over year, to £49.3 million.

Some pieces are conservative enough for Kate Middleton, while others are so ahead of the curve that street style stars, including Style Bubble blogger Susie Lau, wear them to fashion parties and runway shows. Perennial favorites, according to the company, include the "Harlow" varsity jacket—available this season in pink and black for $500—and the "Lauren" A-line leather skirt, $745, which is currently offered in unexpected sky blue.

Now, Shepherdson is betting that the Whistles look will translate in the U.S., where she opened up concessions in three Bloomingdale’s locations last week—with more rollouts along the way. (The retailer’s e-commerce site already ships to the States, and Shopbop.com also sells a selection of styles.) But will American women get it? Shepherdson gave Co.Design a grand tour of Whistles’ offerings at the Bloomingdale’s flagship.

Co.Design: When you joined Whistles, what did you set out to accomplish?

Jane Shepherdson: When we started, Whistles was channeling a bit of a boho thing. Our vision was to create something that was effortless, trend driven, and that provides solutions. "Solutions" is kind of a horrible word, but we wanted to make clothes that were absolutely contemporary but totally appropriate for the kinds of events where you often end up dressing like someone else. You don’t have to look like your mother in law.


You seem to understand the needs and wants of whatever kind of woman you’re trying to attract. Where does that instinct come from?

My starting point was slightly different from most people who run businesses. I was a buyer for a long time, so I come from the creative side. All I want to do is create the most beautiful, perfect things that I myself would want to wear. For me, that’s success. Success is creating something that’s so much better than anybody anticipated or expected. And that was certainly the case with Topshop. We were given total freedom to do whatever, and it worked. And then the profits started coming in and we thought, "Hang on a minute! This is amazing!"

But is it amazing? Not really. Because if you’re creating something that you want and everyone else wants, then of course they’ll want to buy into it. That’s my philosophy. It’s not, "I’m here to make this amount of profit, so therefore I have to drive the margins." The real starting point is the "wow" that makes people stop in their tracks and gets people excited. Because, why else would you do this? If you’re in the fashion business, that’s the kind of thing that gets you up in the morning.

Why did you choose Bloomingdale’s to launch brick-and-mortar in the U.S.?

I think it has an incredible mix of the right contemporary brands. And also, incredible [foot traffic]. It’s rare to find a department store that combines fashion with huge mass appeal. If it can work here...it’s a barometer, I suppose. Also, they’ve got 68 stores around the U.S. We don’t only want to see if we can work in New York, we also want to see if we can work elsewhere, which I’m guessing will be very different.

A lot of U.K. retailers have had trouble building a real business in the U.S. What is your strategy to escape that fate?

I’ve been coming here two or three times a year for the last 20 years, so I know it a bit. We have a lot to learn, and have been humble in our knowledge. We know it’s extremely difficult. I do think the Whistles aesthetics is quite similar to that of New York [women]. The rest of America will be different, but that sort of slightly sporty, laid-back aesthetic is shared. We’ve set ourselves up to be totally flexible so that we can add things in, take things out. I know that other brands have found it hard, but I think some of them come here with a bit of arrogance. Every country’s different. We have a country manager who is amazing. She’s teaching us the nuances of how Americans shop.

One thing American women complain about is that there aren’t enough wear-to-work options out there. That the stuff isn’t cool enough, or it’s not polished enough.

Right, that they’re not representing themselves. I want a woman to be able to just grab a Whistles piece from closet, throw it on, and look amazing. [To feel like] she doesn’t even have to think about it, that it’s not difficult. I also want her to feel like she’s going to stand out just a little bit. Whistles should provide a core wardrobe of pieces that are just easy, comfortable.