Mar 27, 2013 · 8 minutes

Sarah Lacy has written a detailed and persuasive takedown of Amazon's clumsy entrance into fashion retailing. As she mentioned, it grew in part out of a debate she had with me and Adam Penenberg. I agreed to offer a counterargument, because I still think Amazon has a good shot making a successful foray into fashion, despite what we've seen from Amazon so far.

I may be an idiot for making this case, if only because I am an idiot when it comes to fashion. I've been writing about business and finance for 20 years, yet I spent some time in vain this afternoon trying to find a single clip I've written about the fashion industry. Since college, my idea of fashion has been a steadily but barely evolving wardrobe of t-shirts and jeans. (There was a phase in there when I wore a denim jacket too, but let's not talk about that.) My idea of high fashion is lacing up a pair of Chuck Taylors.

I have spent far more time thinking about business models, what makes some companies succeed, and what makes others flounder. And there are several things about the juggernaut Amazon has built in 18 years that make me think that, given enough time and early missteps, Amazon will be a leader here as well as so many other places.

This isn't an idle, academic question. It's one that I'm sure is being discussed inside Amazon a lot these days. Amazon may have been content for years to leave fashion retailing to high-end boutiques. Now, newer stars like Fab and Gilt are not only offering Amazon competition in a growing area of e-tailing, they are pioneering a new phase of ecommerce that could soon make old guys like Amazon and eBay look staid by comparison.

E-commerce was one of the first online business models to catch on because it was all about value. Jeff Bezos understood this better than anyone, battling investors over things like deep discounts, free shipping and Amazon Prime because it meant building, first, customers and later on their loyalty. In ecommerce 2.0, as Sarah says, the focus is less on bargain-hunting, more on shopping. It's about generating demand, not fulfilling demand. It's bringing online one of the last advantages brick and mortars had over the Web: window shopping.

This shift is evident to even a fashion idiot like me. Last year, after hearing much buzz about, I visited the site in a spirit of skepticism and within the hour had become a Bonobos convert, kicking a lifelong Levi's habit. Right now, ecommerce 2.0 is posing an immediate threat to high-end stores and incumbent brands like Levi's. As it grows, it's going to pose more of a problem for Amazon too.

Given all that, it's worrisome that Amazon's entry into both fashion and ecommerce 2.0 isn't drawing much praise. Sarah saw it as confused – scattershot and half-hearted. Amazon may have fumbled its way into the fashion industry, but don't expect it to go away. Count on it to come back with a better, more considered plan that will challenge its chief rivals. I suspect Amazon is tiptoeing in because Bezos knows the company doesn't understand it enough. All-in-ballsiness would be foolhardy right off the bat. But not experimenting with what are essentially a few trial balloons would be even more risky.

Recognizing the need to move into a new market isn't the same as succeeding in it. Here are some things that will aid Amazon as it tries.

1. Amazon's fashion problems aren't insurmountable. Amazon's two biggest barriers to entering the fashion business are its image as a place for online bargains and its traditional weakness in creating content that can drive commerce.

As long as Amazon is seen as the Walmart of the Web, it won't be taken seriously in fashion. In a world where people pay $295 for a hamburger simply because it costs $295, fashion designers won't want to hurt their brand by selling discounts on Amazon. That doesn't mean they have no place there. Rather than driving for value, Amazon could push for exclusivity. For example, Prime subscribers could be given exclusive access to select new high-end products. That would give fashion brands exposure to 10 million Prime members, and establish Amazon as a place to find fashion without having to make the kinds of cheesy videos Sarah mocked.

Then there's the content problem. For window shopping to work in ecommerce, it needs engaging content with a strong point of view. Amazon's site has been designed to be simple and intuitive – that is, it's worked hard to be invisible to shoppers rather than a distinct shopping experience like a high-end brand. Shoppers go there more often to research and buy what they have in mind, not to be seduced into something new. Amazon's DNA is closer to search than discovery.

For Amazon, fixing that image will be the toughest part of becoming a fashion etailer. It means changing how people see the company at a fundamental level. But Amazon has evolved its image many times over the years: as a bookseller moving into CDs and DVDs; as a media-focused site that became more like an online department store, as a store that began making its own gadgets like tablets, and as a ecommerce giant that is also one of the biggest cloud companies. Given all those earlier shifts in Amazon's identity, this one seems relatively subtle.

2. Amazon is nothing if not patient. Compare Amazon's entry into fashion with its move into device manufacturing – a bigger, riskier leap for the company, but one it made only when it saw it was necessary. Skeptics underestimated the Kindle on its debut, and they doubted it again when the iPad arrived as a kind of e-reader on steroids – a Kindle killer. Amazon delivered a popular e-reader right off the bat because it spent several years making it as booklike as possible.

Bezos discussed the Kindle's development in a 2009 interview with Charlie Rose, who asked him what factors most accounted for Amazon's success. Bezos answered,

I think it’s willingness to be long-term oriented and willingness to be misunderstood. Those two things go together. So, you know, we do things that take five, six, seven years -- Kindle is an example -- before they have any meaningful positive impact on our financials. They start out small. We see potential in them. But they’re tiny and they often require great investment. Oftentimes they’re disruptive in some way to an existing industry, and so we, you know, there can be criticism when that happens.
That was the approach Amazon took to online video. Ten years ago, Amazon began working with Microsoft to stream videos on its site. In 2006, it launched its “Unbox” site for downloading movies, a venture quickly overshadowed by iTunes, Netflix, and Hulu. Only recently, after building up a library of TV shows and making shows free for Prime members, has Amazon become a bigger player in online video.

Amazon's enters new markets the way water leaks into a house. It keeps moving, being pulled where the gravity of market forces guides it, eventually finding a way in. Once it finds that, it just keeps on flowing in. I doubt fashion will be any different.

3. Ecommerce still needs fulfillment, and fulfillment is cheaper for Amazon. Sites like Fab have grown quickly because they've figured out how to bring the experience of window shopping online. But they still face the same costs of any etailer, which means either contracting with a third-party logistics company or building the fulfillment infrastructure yourself.

It doesn't cost Amazon nearly as much as a percentage of revenue to move into a new area as it does a startup like Fab to build operations from scratch. As First Round Capital's Phin Barnes explained on Bloomberg TV, Fab faces capital-intensive costs like carrying inventory, building logistics and warehouses and acquiring new customers. Amazon has already built all that in the course of becoming the biggest etailer of them all. More than any single company, it shaped the logistics industry of today. It can expand into fashion with significantly less financial risk than a startup faces.

Startups will also have to spend on marketing to acquire each new loyal customer, and it may need several years before the lifetime value of that customer pays off. Amazon has already established this with Prime.

4. What Amazon can't learn, it can buy. Even if everyone inside Amazon proves incapable of finding a way to offer fashion that resonates with shoppers, the company still has options. Amazon has a strong history of building alliances by making its technology available to others. Making its cloud available to startups through Web Services has established strong ties with developers. Opening its infrastructure to retailers like Toys R' Us has built bridges with rivals.

Amazon can do something similar with the new generation of fashion startups. In the way that an investment in LivingSocial presaged – and probably influenced – Amazon Local, Amazon could buy a stake in a startup hungry for capital. Or it could buy a proven one to give a distinctive face to its fashion storefront. Such acquisitions are rare for Amazon, and a leader like Fab may not want to be bought, but if Amazon is desperate it could easily acquire a second-tier player.

Given the evolution of ecommerce, Amazon will have to make a bolder push into fashion sometime soon. It will face stumbling blocks and speed bumps as it moves down this road. It has several things going for it: A patient, deliberative approach to new markets, an ability to expand cheaply, and the wherewithal to partner or invest in promising startups. If there is durable, steady growth in an area of retail, Amazon will find a strong foothold in it. And will eventually come to be a leader. That was true for ecommerce before, and it will be true for this new wave of ecommerce.