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I don't know how people can buy clothing and shoes without trying them on. But then again, I'm not a woman. Many women, including my wife, love to shop by mail-order catalog. Ann Taylor Stores (NYSE : ANN) hopes that feeling spills over to the Web.

The clothing retailer last month opened its first online store, making the New York company unfashionably late to e-commerce. Other fashion retailers already have been playing dress-up on the Web -- some have been online for over two years. Early participants include Gap (NYSE : GPS), Macy's (a unit of Federated Department Stores (NYSE : FD)), and J. Crew. Last year, Neiman Marcus (NYSE : NMG-A) and J. Jill (Nasdaq : JILL) opened their Web stores.

Whatever the timetable, all of these merchandisers are pioneering new ground, for they must figure out how to hawk fashion in cyberspace to a notoriously fickle market. Unlike the poster children of e-commerce -- books, CDs, electronic equipment, and other easy-to-sell and easy-to-qualify items -- clothes are subject to intensely personal feelings, especially because a wrong choice could make you look fat.

Shopping online for clothes raises challenging issues, says Gomez Advisors analyst Barrett Ladd. How do you answer questions like, "How does this fit me, what does this material feel like?" Ms. Ladd asks. "If you see a picture of black pants, you can't touch it and flip it around to look at the back."

DOES IT FIT?

I asked Andra Ehrenkranz, a senior vice president at Anntaylor.com, about how her company designed its Web business. She says Ann Taylor, with help from the Boston Consulting Group, conducted extensive research by polling existing store customers in their homes, and in some cases, watching them surf the Web for a couple of hours.

Consequently, the Web site tries to provide many of the elements of an in-store experience, albeit in a virtual way. Click for a closeup of an item, for example, to see stitching on a handbag. Ask a virtual wardrobe advisor to see party dresses. Visit a "wardrobe room" to view different combinations of items, such as skirts, tops, and shoes. Customers can use tag numbers from Ann Taylor stores and mailings to order items on the Web.

A Web shopper can "look at any item and change it to the color of her choice," Ms. Ehrenkranz tells me. "On top of that, she can click on a zoom function and get details of any item. It's almost like looking at and touching a garment in a store."

Well, not really. Images on my PC looked flat and colors appeared muted. It was hard to imagine how the "Silver Beaded Camisole" ($118) and "Long Silver Ball Skirt" ($128) would look on someone, when my only real guide was a 3-inch-high image on a headless, armless mannequin.

It's not that fashion e-tail is doomed to fail. It's just that we don't really know yet in what form it'll succeed. One glimpse was provided by Ms. Ehrenkranz, who described a woman who browsed the online store, noted the clothes she liked, then went to her neighborhood Ann Taylor store to try them on. She eventually bought "hundreds of dollars" worth of merchandise, Ms. Ehrenkranz cheerfully informed me.

WORTH TRYING ON

For Ann Taylor and other retailers, the Web now is a big cauldron of experimentation, where they'll learn what works and what flops. Some early evidence of winners points to standard wardrobe items, such as jeans, T-shirts, and shoes from name-brand manufacturers that consumers trust for size and quality. Nordstrom.com (NYSE : JWN) sees its parent's reputation for quality helping to generate an expected $300 million in sales this year.

Retailers must continue rearranging their online storefronts to attract customers or risk being left behind. For Ann Taylor, that means juggling a finicky brick-and-mortar business with investing in a Web operation. Ann Taylor shares this year have been on a roller-coaster ride, and sales appear to be softening, which means the company must keep a tight rein on Internet-related expenses.

Consequently, Ann Taylor's Internet division consists of a modest 25 employees. By comparison, the company's 478 stores, which generated more than $1 billion in sales last year, employ 9,750 people. Many of Anntaylor.com's functions are outsourced. For example, JC Penney (NYSE : JCP)'s JCP Logistics unit handles order processing and shipping, Digitas (Nasdaq : DTAS) designed the Web site, and Convergys (NYSE : CVG) manages customer service and sales.

I asked my wife and a few coworkers what they thought of Ann Taylor, and a simple majority professed to being unabashed fans. I can only conclude from my limited and embarrassingly unscientific poll that there's an army of Ann Taylor shoppers waiting to be satiated online. Will they get what they want? In my wife's case, I fear she will, but not anytime soon.