I understand you can't roll in looking like a slob but I have to think times have changed and the casually dressed founder wouldn't have a problem, even with Wall Street types.
The cultural differences b/t the two industries are pretty interesting though...
Not to mention that humans tend to trust others easier when they are more attractive, e.g., dressed snappy [1]. Imagine that.
It can. You want to dress for the impression you want to make. For Wall St. financial types you probably do want to dress like a banker, since what they're really looking for is professionalism and reliability.
But you wouldn't necessarily want to wear a three piece suit while pitching a media company in Northern California, since what you want to say is "We're not staid, boring people who can't tap into trends and fads."
Interviews are the same way. Overdressing is as bad as underdressing.
Would you be OK with someone in jeans and a hoodie representing you in court?
Would you be OK handing your life savings over to a money manager who was wearing a t-shirt and flip flops?
https://www.youtube.com/watch?v=yJFrkNY4n1g
If you have something of value and the people you are talking to are actually interested in making money, they will get past quite a lot.
(The lawyer question is more ridiculous, they have to work with the prejudices of the judges and lawyers they interact with so only in the narrowest of circumstances would a credible attorney walk into court in jeans)
Consider the duality of U.S. Marines, contrasting dress blues against combat BDU's. Or any military subculture for that matter.
Snappy dressers are trying to send a message about the money they burn on dry cleaning, and how early they get up to look sharp for their morning cup of coffee. How new their razor is, how orderly their coiffure seems. They have the time for this sort of thing, and they might have the time to waste on you ...if you're lucky.
And then there's nerd signaling. The next twelve hours to be spent scanning text, perched atop a swivel chair in comfortable clothes. Waking up possibly before before noon, because yesterday's dose of caffeine and inspiration carried through until 4:30 AM, when someone got their head bitten off in a forum by some cranky sleep-deprived rage about abuse of notation.
Meanwhile, in a court room, lives are irrevocably altered. People being hauled before a judge, to have their lives taken away from them, because they were born under a bad sign. There can't be any flippant hairstyles among the insiders of such a system. The whole point of showing up is to impress upon outsiders that a stone faced institution housed within a forrest of doric columns shall weigh and adjucate a decision. Clear voices in respectable, classic outfits must deliver verbal pronoucements with the reverb of a cavern older than the dawn of humankind. Janitors have mopped blood off these floors. This isn't some cluttered bedroom filled with the detritus of decades old junk.
Takes all kinds.
Why shouldn't it?
I have never seen a lawyer in court with jeans and hoodie or a MM in T and flip flops. However...
Every ambulance chaser lawyers ad I have seen has always had some guy in a suit.
Every big financial crook has been in a very expensive suit.
When looking for a lawyer or advisor I would much prefer to know their track record and referrals/recommendations by others than be impressed by their suits.
That said, because of these bad stereotypes, if I was on the other side of the interview table as a lawyer or advisor I'd be in a suit no questions asked.