Ashley Olsen Spills Her Secrets

There's something genius about seeing the chicest girl in New York all dolled up in tacky cowgirl fringe. I'm sitting with Ashley Olsen at a table in her Greenwich Village town house, looking through a scrapbook—compiled by her great-grandmother—that pretty much tells the story of her and Mary-Kate's blistering rise. The pages are filled with gently yellowed clippings from local newspapers chronicling their toddlerhood on the sitcom Full House through their early years as a two-headed pop-culture juggernaut: the Olsen twins on the publicity circuit in genie costumes; in fairy costumes; in terrycloth robes; in penguin suits; in trenchcoats; in mini-mogul drag; in, yes, cowgirl fringe ... "I look back at the things that we did and the clothes that we wore, and I think, Wow, we really were troupers," says Ashley—although, gazing at some hideous flowered overalls she was put in at age 6 or 7, she has to admit, "I remember really loving those."

What comes across in the photos is the degree to which the girls' lives were engineered. "It was almost like I was in the army," Ashley says. "School, work, homework, fly to New York, get in at 2 in the morning, do a morning show at 5 a.m., then another one at 7, then a radio interview at 10, you know?" Cutesy, coordinated outfits were just part of the drill. The pressure was intense and the scrutiny even more so — "That's why I look at Britney, and I'm surprised I didn't end up like her."

PHOTO GALLERY: SEE PHOTOS FROM ASHLEY OLSEN'S COVER SHOOT

To see Ashley now, it's difficult to fathom that part of her life. At 23, she is very much the master of her own fate, and an icon of defiant personal style. Today she's wearing beige corduroys made exponentially cooler by the fact that she's ripped them up the side seams from hem to shin—and the fact that she's owned them since she was about 15. (Understand: She never, ever throws out clothes. The genie and penguin costumes? All stashed in storage units in L.A. warehouses.) She's paired the beige cords with a signature piece from her and Mary-Kate's fashion line The Row—a supersoft white T-shirt with an artfully stretched-out neck, the short sleeves of which she likes pushing up over her shoulders. Add black flats without socks, tuck the fine blonde hair up under a floppy skateboarder's cap, and the look—at least on her—is just hip and effortless and right.

"I think you're either born with a sense of style or you're not," Ashley says in her small, soft voice, giving her knuckles a loud crack. "Either you care or you don't. And we"—she and Mary-Kate—"love fashion. When we were going to NYU, I think that was the first time we were aware of the power of our personal style. Not the power of it, but the result of it. Between the big sunglasses and the Starbucks cup and the big sweaters, the hobo-chic thing, we were more shocked than anything"—by the endless commentary and tabloid coverage. "I get it; we were fortunate enough to have really nice clothes, and we put them together in this raggedy way. My mom wears glasses this big"—she mimes massive goggles—"from the '70s, and you wonder where we got it from?" She laughs. "The dark eyeliner, the scarf around the head—it's just so interesting and natural." Her family, she says, was "very bohemian."

"Mary-Kate and I are very aware of trends and style, but at the end of the day, we don't even think twice about it. It's just, What do I feel like wearing today, and how do I want to put it together?"

To some extent, Ashley buys the theory that years of being manhandled and styled bred an intense desire in both girls to dress themselves. Eventually, that meant cutting down and altering designer pieces to suit their petite frames—a habit that persists rather feverishly to this day. "The amount of beautiful things we've ruined—not having the patience for a tailor and cutting everything ourselves … My sister once took an Alaïa dress of mine and just cut the whole thing, and then she was like, 'I cut it too short.'" Ashley has to laugh. "Mary-Kate and I don't think about fashion as these clean, beautiful objects. We just kind of wear it and live in it"—and make it their own. When she bought the Daytona watch that's currently on her wrist, she promptly changed the white face to black and the gold links to a crocodile band. In other words, fashion is a way the otherwise elusive Olsens express themselves—most notably through two clothing lines that are somehow thriving despite the cataclysmic retail climate. Ashley and Mary-Kate collaborate closely on Elizabeth and James (named for their siblings), a line that commingles softness and toughness—for instance, slouchy boyfriend jackets and shirts with a flirty ruffle. The idea is to create "a tug-of-war in something with a masculine spirit and a feminine attitude," says Neiman Marcus Fashion Director Ken Downing. "The girls keep nailing it season after season after season. And they single-handedly brought the legging back into fashion." While Mary-Kate tends to conjure the overriding concepts—playing with movie references from Oliver Twist to Hook for the fall '09 collection—Ashley hones in on zippers and buttons and fit. "Nothing gets by them," says their Elizabeth and James partner, Jane Siskin.

The Row, meanwhile, speaks more to their desire for a closetful of what Ashley calls "high-end basics": the perfect blazer, the just-so T-shirt, the cashmere sweater that sort of melts in your hands—with intriguing twists like a seam running up the back. "I just really wanted to make beautiful things," she says. "An educated garment." According to Debi Greenburg, owner of Louis Boston, "Because Ashley's a bit of a type A personality, there's perfection in the way the clothes fit, the way they're cut, that translates on the body beautifully. The Row has become one of my stellar collections here."

Ashley leads me through a few rooms of her town house, haphazardly decorated in battered leather chairs with arms worn down to the stuffing; on the walls are a rare Basquiat self-portrait and three works by Keith Haring that she got at a pawnshop for $30 apiece. In the corner is a drum kit from the Wii game Rock Band, Ashley's new obsession (she plays it at least two hours a night). "I swear to you, it's brought out this whole new thing in me," she says. "I can be a very serious person, and I take my job very seriously, but at the end of the day, I need a break." Her boyfriend, The Hangover's Justin Bartha, also helps in that area. He just called from a press junket in Europe; Ashley signed off with, "Keep your phone by the bed" and "I love you." To say the least, it's been a relief for this pillar of self-sufficiency to have someone she can count on, who puts her ambitions in perspective. "It's more important than anything else in the world," Ashley says.

To read the rest of the interview, pick up the September issue of Marie Claire, on newsstands now.