One of the principal problems in today's world is defining the phrase "better-dressed." As a recent Wall Street Journal article about dressing for job interviews puts it:
To complicate matters, things aren't as cut-and-dried as they were in the days of strict blue-collar and white-collar work uniforms. Following the old dress-for-success rules, with ties and starched white shirts, would create suspicion and awkwardness at Google's dressed-down headquarters today. Executive job seekers have to study more than the balance sheet these days -- they have to suss out a company's fashion ethos. ("Want to Be CEO? You Have to Dress the Part" by Christina Binkley, January 10, 2008, p. D1)
There are certain universals in defining what well-dressed means -- clothes should be clean and stain-free, for example -- but mostly, it's a matter of context. If you went to a job interview at IBM in the 1960s, well-dressed would have meant a clean, starched button-down oxford cloth shirt with a well-tied burgundy tie, a single-breasted charcoal wool suit, and black wingtips. Wear that to an interview with a software development shop today, and your interviewers will probably think you hopelessly stuffy and out-of-touch. It is useless raging about the decline of standards and how that outfit makes you better dressed than your interviewers wearing polo shirts and jeans. They'll still think it, and you will have gone in to your interview with a self-made handicap. And really, your raging would be wrong in any event. Those who own and run that tech company have just as much right to decide on the style of dress that's appropriate for their employees that IBM had back in the '60s. So be smart: ask the person setting up the interview what appropriate dress is for the company or person you're interviewing with, and wear it. If you can't bear the thought of dressing like that, then find another company to interview with.
And it's worth writing that there are almost no contexts where dressing for an interview like the guy in the picture above is appropriate. He's Lapo Elkann, heir to the Fiat fortune. Nobody is going to tell him that he's dressed inappropriately, even if he is.