Tween clothing (for kids 7 to 14 years old) has come a long way since my days of parachute pants. Yes sir, those things were cool. Their "whoosh-whish" sound was handy in notifying your neighborhood friends that you were outside and ready to play. Plus, the pants had the unique ability to disperse and hide your lunch money among the plethora of zipper pockets -- a handy feature if you ever crossed paths with the schoolyard bully.

The days of parachute pants and doing the worm (a classic break-dancing maneuver) on a piece of cardboard is long gone. Today it's low-rise boot-cut jeans and tight tees that are filling the seats of the yellow bus. Style comes and goes, but the one constant remains: There is money to be made from kids.

The Limited (NYSE:LTD) saw this market as a unique opportunity and launched the Too (NYSE:TOO) line. Since it was spun off by its parent company, Too has now amassed more than 600 stores (including its Justice units), attacking this part of the retailing industry with vigor. But store expansion has not resulted in a stellar investment.

I noted in a prior look at Too that the past five years have been filled with inconsistencies, equaling an average investment at best. However, the company was showing signs of gaining traction, and the most recent glance by fellow Fool Alyce Lomax suggests its concept may be turning the corner for the better. Shareholders certainly are feeling good right now, with the stock up about 50% over the past three months.

Is it time for Too in your closet of stocks? I still have my reservations. Of all of the age groups, the tween crowd must be one of the most difficult to satisfy. Parents don't mind spending good money on their child's back-to-school attire when their job and the economy are on the up and up. But spending $50-plus on a pair of jeans that their 10-year-old daughter will outgrow in a year isn't likely to happen when families are buttoning down their financial hatches.

This reality puts high-end private labels such as Da-Nang, Diesel, Juicy Couture, and Von Dutch at a greater risk. It's also why value-conscious mass merchants will continue to play a critical role in this market. Target (NYSE:TGT) and Wal-Mart (NYSE:WMT) will never be confused for fashion trendsetters, but for parents footing the bill, that doesn't matter.

Aside from the ups and downs of economic sentiment, Too also faces a significant challenge in remaining fashionable. Retailers such as Gap (NYSE:GPS) and Abercrombie & Fitch (NYSE:ANF) have the built-in advantage of catering to a broader audience. Since impressionable tweens strive to look older and wear what high schoolers and the college crowd are sporting, this puts increased strain on tween-specific retailers to be relevant and cool. Not surprisingly, research firm NPD advised in its report of the tween market that it is critical for apparel retailers to "diversify their target audiences."

And this has nothing to say about another critical risk Too investors must deal with: The premium of its valuation as noted by Alyce. Given the tremendous uncertainty in this market, those who want a piece of this tween retailer in their portfolio need to buy with a significant safety margin.

Gap is a Motley Fool Stock Advisor recommendation.

Fool contributor Jeremy MacNealy does not own shares in any of the companies mentioned.