At any number of high-tech companies I’ve worked for, wearing any kind of nice clothes (especially a suit) to the office immediately put you under suspicion of interviewing at another company.
These days you don’t even need to wear nice clothes for an interview.
One thing DH has noticed, the people who wore tee shirts twenty years ago now wear very casual but very expensive tee shirts etc. You can usually tell by the sweaters and shoes how successful someone is. Many are wearing jeans and a shirt, but the jeans are hip and the shoes cost $800. Suits have been out forever ( except for meetings in Europe and Asia). Even at the larger companies this is the case at the higher levels. For VC’s and CEO’s, it’s not just a tee shirt, it’s a certain type of shirt (even if it it is a tee) . It starts to look a little silly when you are in your 50’s wearing sneakers. For the techy types, the nerd look is still mainstream. But again with success comes a bit more style ( not always but often). The I’m so hip I wear dirty tee shirts and the sneakers I had in college can be seen somewhat negatively.
Usually, I saw this kind of thing with men interviewing out of college, or student summer interns, where they probably look worse in “dressier” clothes than they would in the casual clothes they usually wear. (They might also not have, or be willing to spend, the money to buy better fitting “dressier” clothes.)
But then it probably is not surprising that if you have someone wear something that they normally do not wear, the cosmetic result is less than optimal.
My S and SIL work in New York where the dress code is more formal than Silicon Valley and how you dress is more relevant according to whether you are servicing clients or you are the client.
My S is an investment professional at a hedge fund (no retail business) and he invariably is always the client. He usually wears a collared shirt and khaki pants but on casual fridays, he wears t shirts and jeans. He tells me at meetings and conventions people wear more sports jackets than suits.
I remember his undergrad business school (Wharton) requested all incoming first year students to bring a suit. That was almost 20 years ago. He worked at an investment bank after graduation where people generally wore suits.
Meanwhile my SIL is a partner at a Vault top 5 law firm. He services clients and always wears a suit, no tie unless he is making presentations. My D took a recent photo of him zooming with his shirt, tie and suit jacket top half and shorts below.
Attorneys still wear suits in court to my knowledge. And I have some clients who still expect me to be in a suit (even on Zoom calls). You can argue suits have been out forever. But don’t be surpised if you find youself transferred off that client at some point. Number of clients with that view is shrinking but they still exist. Ignore that at your peril.
Point to my son with all of this was to think what you are wearing. May not be what you want to wear. But what is expected and who are you seeing. “I wore what I wanted to wear and was really comfortable” isn’t so great if you lost or didn’t get the business. Unless you are either so busy you don’t need the additional business or are a driver of expecations.
At one point I would always advise guys to have a decent suit (doesn’t need to be expensive) that fits. If nothing else you will go to funerals and weddings. But now you see them less often at those events. So now maybe you take a step down and say a decent pair of dress pants (again that fit) and a couple decent shirts and a sport coat/blazer. You may not wear them often but you likely will need them at some point or another.
@saillakeerie Perhaps you are referring to the legal industry where suits are still worn and de rigeur. But the previous posters were mainly speaking about those in tech and more specifically in Silicon Valley. There you would be the only one wearing a suit and you might feel strange. And not to mention, you would likely be very warm.
It is good to know what a client expects. It’s also good to be on the better dressed side. If you are wearing something in between like the high end business casual look, it’s likely it’s a non-issue. If you are wearing old sneakers, it’s likely the client is going to hold you to a higher standard.
Not to mention client facing and non-client facing. In many fields, there are client facing people and those who are very very intelligent who would not be put in front of a client for any reason ( it often has to do with manners and dress/personal hygiene). Some don’t realize they are not client facing or don’t wish to be. Others would like to be promoted but are contained in a more technical role (often for the same reasons). When kids are younger they focus a lot on how much they make and what they do. As they get older, it gets harder to break out of some molds. So while your kid might be casual and think it’s cool to have holes in their shirts, somewhere someplace is likely thinking they aren’t client facing. This can have negative long term implications for their career.
I think the old business attire actually made it easier for most. Now, clothing has an entirely new aspect in terms of careers esp for men.
I didn’t think people in Silicon Valley ever wore suits. So they were never in to be out. 
I agree that it makes sense to error on the better dressed side. When in doubt, take the better dressed option. If you have confirmation its the lower dressed side, have at it.
My son may work in SV, but there are family functions that need a suit and nice shoes. Also, long sleeve shirts &decent pants.
Everyone needs something appropriate for “marryin’ and buryin’” (weddings and funerals). Though, I know even some of these events are casual now.
We bought our son a suit before senior year of college, but he was an engineering student so never needed it for interviewing (on campus interviews, which were directed to be business casual or sometimes Tshirt/jeans). He has worn it a few times for formal events, but I think the blue blazer, from same purchase as “2nd item free”, has gotten more use.
My daughter’s boyfriend is in a wedding this weekend. They rented suits. Not tuxes, suits.
If you only needed a suit for marryin and buryin ?, then a rented suit would be just fine. Especially if you are like my husband and seem to be a different size every time an event happened.
He hasn’t even worn a suit to a funeral lately as he doesn’t have any dress shoes at the moment.
My D’s wedding had the guys in rented suits. My S didn’t want to be in the wedding, but he walked me down the aisle in a suit … no tie. I think he got his fill of ties in parochial school! He is a lab chemist, so he definitely doesn’t wear a suit/tie to work. H was an engineer for an auto company, and they dressed quite casually by the end of his career.
Times have changed.
Went to a funeral in February, small town Texas. My H asked if he needed to wear a suit. I said yes! All the other men were in khakis and polos. Oops. Small family funeral.
Allbirds rather than sneakers in that crowd. At least earlier this year.
As you point out @Happytimes2001, people figure out how to signal prestige or create a caste system even out of jeans and a t-shirt.
Has anyone mentioned the 25x Rule in the previous posts? I find it may be applicable to some of us.
“The 25x Rule To Early Retirement” by Rob Berger (2/23/2017)
https://www.forbes.com/sites/robertberger/2017/02/23/the-25x-rule-to-early-retirement/#6386ce736faf
But at the same time, you need to be cautious about “how retirement affects your health.”
https://www.livescience.com/40976-how-retirement-affects-your-health.html
It was probably mentioned earlier in the context of FIRE (financially independent retire early).
Not everyone wants to retire early. But being able to retire early does add some financial protection against job obsolescence, age discrimination, seniority discrimination, etc. that can end your current career involuntarily. Since it can take a while at low or no income to change careers, having retirement level savings and investments can give you that opportunity, rather than being forced to take whatever subsistence job is available to pay the bills in the short term.
The 25x rule has been mentioned a few times. It’s a good place to start, and it does help people saving for retirement realize they need to save a lot.
As pointed out in the article, it would be 25x the amount you need after pensions/SS. But how much does a couple need, once they are no longer saving for college and retirement? It’s a good idea track spending for a few years while getting into retirement planning mode. That can help validate your retirement financial model.
When tracking spending to estimate retirement spending levels, be sure to consider:
The 25x rule is just a restatement of the 4% rule, and there’s a lot of debate about whether a 4% after-inflation return is really feasible any more without excessive risk, given the current low interest rate environment that isn’t going to change for the foreseeable future. We debated it here quite a bit in the past. 3.5% or even 3% may be a more conservative approach to make sure you don’t run out of money.
I pulled a bunch of money out of the stock market last week (I’m now about 50% in stocks) so of course the market has continued to climb since then. Y’all are welcome. 