Ann Taylor (NYSE:ANN) has been busting at the seams lately when it comes to having aggressive plans. The latest example is its strategy to offer a new high-end fashion line that will feature apparel priced up to 40% higher than its regular merchandise.

The new collection, which includes about 50 items, will be called Collection (rather uninspiring as far as names go, but it shares the name with J. Crew's (NYSE:JCG) high-end, limited-edition brand called Collection, oddly enough). The higher-priced pieces will be featured in 24 of Ann Taylor's best-situated, highest-performing stores, set aside in a separate section from the regular merchandise. (The Collection collection will also be available on Ann Taylor's website, for those of us who aren't near places like New York's Madison Avenue.)

Targeting an affluent customer is nothing new in retail, since there's the argument that wealthy customers are always willing to spend, regardless of the macroeconomic environment. Truly wealthy shoppers just aren't going to experience the sticker shock that others will.

There are many signs that retailers and brands covet the high-end and discount markets, since it's the middle-of-the-road brands that seem to have trouble these days, judging by the situation at department stores like Macy's, and even Ann Taylor's sluggish growth recently. Consumer goods company VF (NYSE:VFC) is reaching for the stars, too, making moves like selling its Vanity Fair brand to Berkshire Hathaway's (NYSE:BRK-A) (NYSE:BRK-B) Fruit of the Loom, trying to give its Nautica brand a more upscale sheen, and snapping up premium denim brand Seven For All Mankind.

Many savvy female shoppers who aren't rolling in the dough play both sides and avoid the middle -- get some cheap chic someplace like Target to save a few dollars, yet pay up for some irresistible, pricier item somewhere like Nordstrom (NYSE:JWN) or Coach (NYSE:COH). However, these are the same women who just may balk at high-priced goods at Ann Taylor, and these may be the same women who will make or break this strategy.

Ultimately, Ann Taylor's news came as a surprise to me, considering the fact that the retailer recently said it's launching a new concept for the "modern" baby boomer. I suppose it occurred to me that maybe Ann Taylor's got plenty on its plate already between a new concept's strategy and reinvigorating its core concept and Loft.

Furthermore, I can't help but wonder if launching a high-end brand side by side with its existing merchandise isn't a risky proposition. The Collection's pieces will reportedly be made with higher-quality materials, ostensibly making them worth the markup. But will that really convince Ann Taylor's existing customers to pay up, and what does it say about the retailer's other apparel -- and will it draw truly upscale shoppers who may have an entirely different impression of Ann Taylor's brand?

It should be interesting to see if Ann Taylor can pull off all its high-flying plans. It's got plenty of them, but that doesn't mean they will necessarily spark growth for the retailer. 

This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.