Have you seen Ameriprise Financial's (NYSE: AMP) latest commercials featuring Dennis Hopper? Dressed in a sharp black shirt with the Spencer Davis Group's "Gimme Some Lovin'" playing in the background, Hopper tells boomers preparing for retirement: "Your generation is definitely not heading for bingo night."

Like many of the financial stocks, Ameriprise has taken it on the chin lately. But the company exceeded fourth-quarter expectations with a 49% increase in profits on growth in its wealthy-investor business. Based on these recent results, it looks like Ameriprise is onto something with this hip advertising campaign.

Contrast this success with the recent falling stock prices of "boomer-focused" retail companies like Chico's (NYSE: CHS) and Coldwater Creek (Nasdaq: CWTR). A new reality may be setting in: If 60 really is the new 40, it could spell big trouble for specialty retailers.

The mighty have fallen
The premise of these stores, and others in the same genre such as Stein Mart (Nasdaq: SMRT), Christopher & Banks (NYSE: CBK), and Talbots (NYSE: TLB), seemed like a smart one: Focus on boomer ladies who have strong tastes in fashion and expendable incomes. With the latest "mature" styles and sales staffs in attendance for every detail, these companies had great growth rates and seemed to be strong bets.

However, these stocks have fallen as hard as any in the retail sector. Christopher & Banks has lost more than 40% of its value in the past two years; the others are down a much steeper 70%-80%. An iffy economy has certainly contributed to these stock declines. But something else could also be to blame: Boomer women don't want to be considered "old ladies."

Granny pants: out; young and hip: in
In her new book, How Not to Look Old, style expert Charla Krupp provides what she calls the "boomer manifesto" for looking younger and better. She says, "Looking younger isn't just about vanity. ... Looking good is about our personal and financial survival."

As Krupp points out, wearing "mommy jeans" or "granny pants" lets the world know that you are an "old lady." To avoid that stigma, the book suggests tips on how to look "Younger & Hipper." Women are buying this advice in droves; the book is on The New York Times top-10 best-seller list of hardcover advice books.

What's ironic is that the same focus on mature styles that initially made Chico's, Talbots, and the others popular now seems to be what's keeping women out of their stores today. The question for investors is whether retailers will buy into the boomer "younger is better" mind-set. Ann Taylor (NYSE: ANN) has said as much with its recent announcement for plans to target modern baby boomer women in a new store concept.

Buy low, sell lower?
Even with attractive valuations, it's hard to predict whether these companies will rebound soon. While companies like Ameriprise can quickly give themselves extreme makeovers to acknowledge a baby boomer mind-set change, the retail cycle makes it harder for specialty retailers to regroup and change course.

For instance, as early as 2006, Chico's saw declining same-store sales growth attributed to "unexciting merchandise and tired marketing programs." Yet while the company quickly made changes to its advertising campaign by ditching the "make it a Chico's day" ads, leftover inventory and advance orders for next season's offerings made it impossible for Chico's to deliver a wholesale change in strategy with immediate impact.

Given those challenges, it remains to be seen how boomer-focused retailers will react to these trends. In the meantime, unless fickle consumers change their minds and decide that granny pants are in after all, the retailers have an uphill climb ahead.

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