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

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

Behind these headlines lie three very different perspectives on how to reach a more tech-savvy, younger buyer. And the results are extremely mixed.

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

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