I had learned from the store owner that you can tell so much from someone's shoes, often more than from their clothes.
Combined with that line in this very formative movie (for me), I still to this day can't help but check someone's shoes when I first meet them.
You can make educated guesses based on apparel of all sorts - but you are always guessing.
Shoes are indeed a valuable source of information about a person. I knew at least one BH case manager who really paid attention to them.
Shoes are expensive, very durable, and typically one of those items that people have only a few pairs of. So while someone can easily change their outfit to match a situation, place, or mood for the day, they may be less likely to change their shoes to match more than a basic purpose.
And shoes tend to accumulate evidence of where someone's been. Are they muddy, dusty, spit-polished?
Personally, I own about five pair of shoes. I have a pair of Oxford dress shoes, a very nice pair of white New Balance with hook-and-loop, some hiking boots I picked up at JC Penney, and a few others. My clothing, on the other hand, is mostly Adidas and Columbia and some tee shirts, but I don't own any Adidas or Columbia shoes. So you can tell a lot about me, no matter what I'm wearing, by studying my shoes for a while.
I met another BH professional who said he owned 52 pairs of Crocs. He said that he'd kicked an addiction habit, but it seems he traded something unhealthy for perhaps a less-detrimental dependence on collecting shoes. To each his own, I suppose, and surely a lot of information could be gleaned about this fellow if you paid attention to which pair of Crocs he'd selected for the day.
Maybe that used to be true, but modern shoes while expensive are not very durable, and most people have several pairs today.
Someone wearing pristine white Jordans, Red Wings boots, or bottom tier Cole Hann dress shoes can all say things about a person.
When I first watched this movie, I felt like this was a weak moment in the film. "Computer dating" at the time was laughably bad, so seeing a character regard it as infallible ruined the immersion.
With age and experience, I now see that some people just throw themselves behind certain technologies, and fail to find flaw. So maybe this character was just a misguided computer dating evangelist, blind to the technology's failings.
"...Fellas. Fellas, look at this man's trash. He's not looking for "buff." The man who folded this tube of Crest...is looking for someone...meticulous. Refined. Anal. ...What?"
I think Cosmo's comment - note he's extremely vain, how he dresses, his office is practically a modern art gallery, he's got the organization's Cray sitting on display, etc - just further shows how vain he is, thinking someone as attractive as Liz couldn't possibly be a good match for a nerd like Werner, when it's established that they're actually quite alike/compatible.
One could imagine that Liz also obeys all speed limits and comes to complete stops at every stop sign...
Cosmo has been in prison for a long time. His perception of dating service implications are unlikely to be contemporary.
Marty: Organised crime?
Cosmo: Trust me, it ain't that organised!* It's not about computers and them (Liz and Werner). It's about Cosmo.
* Computer dating is about algorithms and pattern matching. Cosmo didn't have any suspicion of Liz and Werner going on a date; even if he saw a type-mismatch, humans are complex and multi-faceted. But when he learned a computer program ostensibly made the match, his alarm bells went off.
A couple of scenes:
And another: