Three old-school brand names made financial news headlines thisweek, all for the methods they're using to adapt to a new economicreality.

• J.C. Penney Co. Inc., the place where mom usedto take you to do your back-to-school shopping, reported lousysecond-quarter results: comparable-store sales down almost 22percent, traffic down 12 percent, all leading to a $147 million netloss. Where did they go wrong? CEO Ron Johnson admits they felldown on marketing and pricing.
• Sears Holdings Corp., theonce-mighty retailer that was at one time synonymous with theMiddle American consumer but now struggling for a foothold in aWal-Mart world, announced plans to spin off its remaining Hometownand certain hardware stores, independently owned venues that offerSears-branded appliances, consumer electronics and lawn and gardenequipment. The move is expected to raise as much as $500million.
• Allstate is seeing online auto policies soldby recently acquired Esurance increase by 13percent through June 30. The strategy seems to be working: Allstatestock is up 39 percent in 2012.

Behind these headlines lie three very different perspectives onhow to reach a more tech-savvy, younger buyer. And the results areextremely mixed.

Penney's marketing campaign “overreached our core customer,” CEOJohnson admitted. I have no clue what Penney's customerdemographics are anymore, and I get the feeling Penney's doesn'tknow, either. Earlier this year they rocked the boat by runningprint ads featuring same-sex parents; and its plans for thedepartment stores feature a combination of the traditional and thewacky. While customers will be able to use mobile checkout in allstores, Penney also seems to be banking on building abricks-and-mortar atmosphere that sounds like a mash-up ofStarbucks, Apple and I don't know what. Johnson said thechain will expand its aisles to 15 feet wide, calling then “TheStreet” and “creating a place for customers to engage.” The Streetwill feature coffee and juice bars, couches and tables with IPads,and the store's center — called “The Square” — will host activitieslike Pilates and yoga.

This from a man who admits that the store's second-quarterlosses resulted from ignoring the core customer.

I don't know about you, but when I'm in the mood to pick out apackage of underwear, I don't want to “engage” withanyone, drink juice or do yoga. I want to pay for my underwearand get the hell out. But maybe JCP's targeted demographic isedgier than I am.

Meanwhile, admittedly stodgy old Sears may have the right idea.By unloading its Hometown stores, they'll still get the revenuefrom selling Kenmore appliances, Craftsman tools and DieHardbatteries, without the overhead of running a franchise.

And then, of course, there's Allstate. The Good Hands' purchaseof the digital Esurance brand for $1 billion late last year hasstuck in the craw of its agents, who see their clientsdefecting to the cheaper brand.

On the face of it, Allstate's investment in Esurance seems to bea smart move, at least for the company. Second-quarter net incomerose to $423 million, compared with last year's net loss of$624 million due to huge cat losses.

But in 2012, loss trends have worsened at Esurance, andAllstate's big marketing investment in the online insurer meansEsurance spent $1.22 for every dollar of premium it collectedin the first half of 2012.

Independent insurance agents know all about the risks inherentin “churning” business, a practice that Esurance and other onlineinsurers are learning for themselves.

In its attempts to be all things to all people, Penney's isconfusing itself with Starbucks, Sears with McDonald's, andAllstate is hedging its bets between the traditional distributionsystem, Flo and the gecko.

Freud once famously asked what women want. Old-school brandsmight ask the same question about customers in general. They mighteven want to ask independent insurance agents about how theyfigured out quite a while ago that they can't be all things to allpeople.