Remember when Gap's (NYSE:GPS) Old Navy concept was new? It's certainly been a while, and investors and retail watchers will be interested to note that Gap's got a new concept on the launching pad. It plans to open a specialty store chain that appeals to a more mature female demographic.

Gap, which happens to be a Motley Fool Stock Advisor pick, has been trying to pull off a turnaround for quite some time. It's been launching several initiatives to move away from its image of targeting a teenage demographic or khaki-wearing conformists, including an ad campaign with Sarah Jessica Parker and a plus-sized experiment at Old Navy.

After having experienced what one can only imagine are significant teenage defections to retailers such as the wildly popularAeropostale (NYSE:ARO), Gap may very well hope to ride on the coattails of the also-wild success of Chico's (NYSE:CHS) with its new concept.

Chico's most certainly has been on fire, thanks to its popularity with fashionable women around the ages of 35 to 55. Ann Taylor (NYSE:ANN) -- and especially its Loft concept -- has also struck a chord with women in their twenties and on up, and it's likely also been swiping some of those shoppers from Gap.

Gap's idea is definitely a logical one. Older women these days tend to have more cash in their wallets than their younger counterparts -- and the boomer generation is a crowd, by definition. However, challenges are there -- Talbots (NYSE:TLB) and J. Jill (NASDAQ:JILL) show examples of retail concepts that have struggled as older women's tastes and views have changed over recent years.

Is Gap up to the challenge? Personally, I've felt Gap has been out of touch for quite some time. My own occasional trips into its stores over the last year or two just haven't yielded any urge to buy, though that urge seems to occur awfully often a few stores down at Ann Taylor Loft (though I'll buy the occasional pair of jeans at Old Navy because they don't break the bank). Over the summer I ventured into Gap, and while a few items appealed a little bit more on style, I didn't like the way the material felt. These observations (as well as Gap's relatively empty stores) have fueled my own nagging doubts about the retailer's relevance today.

For investors who are banking on Gap turning around its fortunes to the popular days of yore, they'd better be hoping that it's been doing its homework. While it's picked a good demographic to target, it's also got formidable competition in that space.

Gap is a Motley Fool Stock Advisor pick. What other stocks are marked for success? Try it for six months, risk-free. Or, log onto our Gap discussion board, where you can give your opinion of whether Gap's winning or losing.

Alyce Lomax does not own shares of any of the companies mentioned.