When trying to change potential customers’ misconceptions about your brand, do you address those misconceptions outright or avoid them altogether? Sister brands Kmart and Sears take opposing approaches in the September issue of Vogue.

One doesn’t expect to see ads from Kmart and Sears in Vogue. Vogue is the aristocratic doyenne of the fashion magazines, and the September issue is where luxury brands and designers must be seen—if not on the editorial pages, then definitely among the advertisements that far outnumber the articles.

Of course, that’s exactly why Kmart and Sears bought ads in the issue.

Neither Sears nor Kmart is perceived as a place to shop for stylish clothing. Sears has a great reputation for its Kenmore appliances and Craftsman tools. But people who come to one of its stores or Sears.com to buy a fridge or a power screwdriver rarely mosey over to the women’s apparel section to browse through the dresses or purses. Kmart, meanwhile, was long known for its “blue-light specials ” and as a place for cheap knockoffs and inexpensive housewares.

For the longest while, neither brand was able to do what Target managed: to give its wares an aura of fashionability.

But they’ve been trying. Kmart in particular, with its Kmart Design initiative, which includes a dedicated Website and Facebook page, has been working to “get people to rethink the apparel and home businesses,” Jeff Fagel, director of brand management, told me a few months back.

Which brings us to the Vogue ads. First, the four-page Kmart insert. “It’s true,” reads the headline, in green against a black-and-white close-up of a fashionably tousle-haired model. “The best looks of the season. Right here. Right now,” is the follow-up copy, atop the Kmart logo. The logo and/or the URL kmart.com/it’strue appears on each of the remaining three pages, which feature the same model posing in wearable, on-trend separates.

Conversely, the Sears logo appears only once on its four-page ad insert, tucked away like a wallflower in the lower left corner of the final page. The only text on the opening page, “Why take sides,” appears beside a color photo of another fashionably tousled-hair model. The inside spread features the same model posing in wearable, on-trend separates alongside the URL themanysidesofme.com. When you do finally come across the Sears logo on the final page, it doesn’t clarify matters. I wasn’t sure whether the ad was for Sears or for an apparel brand called the Many Sides of Me that happened to be sold at Sears.

So I input www.themanysidesofme.com and was directed to a landing page on Sears.com featuring a slide show of images from the ads (see above). The ads go to great lengths not to have these fashionable items “tarnished” with the Sears brand, so I was startled to see the creative from the ads surrounded by the same page headers, tabs, and navigation as the rest of the Sears site.

All of this reminded me of when I’d be out with my college boyfriend. He was smart, fun, friendly, but the worst dresser I’d ever seen. If we were out together and I spied someone from high school, I’d remove my hand from his clutch and walk a bit apart from him so that my former classmate wouldn’t think I was actually dating this loser. (Shallow, I know. Eventually I matured enough to marry the guy, and he was willing to submit to a makeover. He became a pretty sharp dresser, just in time for him to meet the woman he married a few weeks after our divorce was finalized. I believe she owes me a thank-you.)

In short, these fashionable togs don’t want to be associated with Sears in public (the pages of Vogue), but in private (when trying to close a sale) it’s a different matter.

The call to action on the landing page is a button labeled “Shop our collection.” This takes you to the women’s clothing section of Sears.com. The main image is still a slide show from the ad insert, and beside it is the link “Shop Apostrophe.” Apparently these items are from Sears’ Apostrophe range.

So why didn’t Sears simply highlight Apostrophe in its ads? By being so coy about the branding in its ads, it seems to be promoting the perceived gap between its top-quality hard goods and less-favorably viewed soft goods.

Kmart, on the other hand, not only recognizes the proverbial elephant in the room—the perception that its clothing is hardly fashion-forward—it saddles the elephant and takes it for a ride. Upon hearing that Kmart has a team of designers who have worked with designers such as Oscar de la Renta and Ralph Lauren, Fagel said, people tend to react with “curious disbelief.” With its copy, and even the name of the dedicated URL, Kmart makes that curious disbelief the centerpiece of its efforts.

Typing into your browser www.kmart.com/it’strue, by the way, takes you to a landing page on Kmart.com, just as Sears’ special URL did. But this time you’re expecting it, so it’s not at all disconcerting. In addition to allowing you to start shopping then and there, the landing page includes links to a behind-the-scenes video and to Kmartdesign.com, where you can “shop the trends” as well as learn more about Kmart’s design pedigree.

I prefer Kmart’s overall approach. There’s something furtive about Sears’ effort, despite its presence in Vogue (and several other big-name fashion magazines as well). If you want to destroy misconceptions, do it boldly, like Kmart does. Otherwise some people might wonder if your hesitancy indicates that there’s more than a little truth in the misconception after all.