Lands’ End launched its website in 1995, the same year Amazon and eBay were founded. Initially, the site featured 100 products as well as stories, essays, and travelogues. Today, the US site offers every Lands’ End product from all of its different catalogs. The company operates separate websites for the United Kingdom, Japan, and Germany. Through its “Business Outfitters” division, Lands’ End serves the corporate market.

From its modest beginnings in 1963 as a Chicago merchant selling sailing-related gear and clothing, Lands’ End has become a US$ 2 billion online retailing giant owned by Sears (more about that later). And virtually everything Lands’ End sells is branded with its own name. The company’s staple is still upscale clothing, but it has expanded into other merchandise areas, such as bedding, towels, luggage, and furniture.

Despite the fact that it is a big company, it’s the human side of selling that Lands’ End strives for. Lands’ End boasts some of the most personable customer service representatives in the industry, quality products that provide excellent value, a liberal return policy, and a lifetime satisfaction guarantee.

Lands’ End seems friendly, approachable, and customer-aware. They don’t just sell swimwear, they let you choose suits by “anxiety zones”—areas of the body you want to accentuate or camouflage. If you need your questions answered but prefer not to call, that’s okay—you can chat live online with a customer service representative.

Lands’ End has a kind of genuine down-home brand personality that can’t be artificially manufactured. For example, the company sheepishly admits on its website that the name “Lands’ End” was a mistake—the apostrophe is in the wrong place because of a typo in the company’s first printed piece. The founder couldn’t afford to have it reprinted. Now that apostrophe has become symbolic of the company’s individuality.

So why then, in 2002, did Lands’ End sell out to mainstream retailer Sears? A cynical but accurate view might be that founder Gary Comer wanted to cash out after almost forty years. (Comer died of cancer in 2006.) Another likely reason: Lands’ End had grabbed the lion’s share of the upscale online apparel market and the next best area for growth was in brick-and-mortar retailing.

At the time of the Lands’ End acquisition, Sears had about 870 stores and about US$ 40 billion in sales as the nation’s fourth largest retailer. (This was prior to its 2005 merger with Kmart.) If Lands’ End was looking for broad market penetration, Sears fit the bill. Sears, on the other hand, had a kind of bread-and-butter image that could only be enhanced by the quality offerings of Lands’ End.

The plan was to operate Lands’ End as a separate entity and leave its mail order business largely alone, but its celebrated clothing line would begin to show up in Sears stores. Today, you will find the “Lands’ End Shop at Sears” in about 150 Sears stores in over 20 US states. The stores are polished and upscale. The products are prominently yet elegantly branded in Lands’ End blue and white.

The fact is, to some Sears shoppers, the Lands’ End Shop might look out of place. Sears stores themselves do not have the same trendy elegance as do the Lands’ End Shops. It is, in effect, physical evidence of the disparity of two well-known brands that, despite a corporate marriage, target entirely different audience types. Sears’ existing customer is probably not a Lands’ End mail order buyer, and the Lands’ End mail order buyer typically doesn’t shop at Sears.

Yet Lands’ End clothing offers Sears a quality apparel brand that it can sell exclusively—and that could help it compete against other low-price retailers like Kohl’s and Target who have dominated the department store clothing market in recent years.

After the Sears-Kmart merger in 2005, rumors of a Lands’ End sale began to surface. But in April 2005, Sears chairman Edward S. Lampert told a shareholders meeting that he had no intention of selling the Lands’ End brand.

So for now, Lands’ End will walk an interesting, somewhat precarious line. The company will continue to market its products, as it always has done, via the mail order channel, where it remains one of the best-known, highest quality brands in the business. And, assuming it remains part of Sears Holdings, Lands’ End will also continue to market its apparel in Sears stores—where it has the potential to increase revenue via the traditional retail channel.

The impact on each brand will be worth watching. Will Sears move upstream because of the Lands’ End brand image? Or will the Lands’ End brand move downstream as it reaches more of a mass market through Sears? It will be interesting to see who sinks and who swims.

Barry Silverstein has been a frequent brandchannel contributor since 2007. He has thirty years of advertising and marketing experience and is currently a freelance writer and marketing consultant. He founded and ran his own direct marketing agency and held executive positions with Epsilon, a leading database marketing firm and Arnold, a major ad agency. Silverstein is the author of three marketing books, including the McGraw-Hill book, The Breakaway Brand, which he co-authored with Arnold CEO Fran Kelly.