I prefer to buy new and then "use it up, wear it out, make it last". (slogan from WWII era).
My outdoor propane grill is 19 years old and still works OK. I have had one bathrobe for at least two decades according to old photographs. My car is a 1999 model, as is my bicycle. I could go on. I believe this is much better even than buying someone else's used stuff.
A large portion of products we buy in second hand stores are children's toys and clothing. The prices of new toys are insane, we leave a second hand store about once a month with a large bag of stuffed toys, board games, worn in shoes, skates etc. for the cost of a single new item. Kids don't care at all and mine refuses to wear new shoes even.
That's how we got reintroduced to thrifting/preowned shopping/whatever you want to call it: we had a kid. It wasn't even so much a financial thing as it was this sense that otherwise there would be so much waste (the financial aspect is nice though too). So many clothes and toys that are just fine but they grow out of them. After that we started looking into stuff for ourselves.
Depending on what it is and how hard you use it compared to the average buying a bunch of pre-used ones and running them into the ground can be cheaper.
That's something I wonder about. Something to keep in mind with preowned items is that not all preowned items have been used heavily. Some have been used a bit and then someone doesn't like it for some idiosyncratic reason, and then wants to recoup losses. Sometimes this happens for a reason that's important to be attentive to, but sometimes it's just idiosyncratic to the purchaser. Clothes are a good example: someone might get a wrong size for a gift or something, maybe wear it a few times, and then decide it's not going to work.
A little use can be good too because it's already stress tested a bit. It depends on the item.
I've had good and bad luck with used and new items for different reasons. A new item can be more of a roll of the dice in some ways, but used items can be too in their own way.
Buying new means immediate depreciation on the value of the item. I prefer to buy used and be able to resell at (or sometimes above) roughly the price I paid if/when necessary.
Anything that is not fast fashion is welcomed. Fast fashion is morally corrupt and preys on younger generation to fit in with the latest trends. I bought 30 black t-shirts and 15 black tracksuit bottoms and never have to make the decision of what to wear.
It's also been nice to see retailers like Patagonia playing along the trend. Buying a $250 coat, trading it in for a $50 credit, Patagonia reselling it for $80. Unclear about the net gains when factoring in shipping + cleaning, but at least it keeps objects with a 20-year-lifespan out of the landfill by year 4.
The important change is that it used to be a low-status activity, but now it's becoming a higher-status activity — at least until middle-class people get bored of instagramming their thrift-shop finds.
Although, the upper classes have always valued re-use and handing down. Alan Clark (not a man who would have thrived in today's political environment) once said: "The trouble with Michael Heseltine is that he had to buy his own furniture" i.e., he was lower class. There was a similarly snippy remark made about the furniture in Katherine Middleton's (Duchess of Cambridge) family home—it was too neat and new.
Here is a catchy tune that was a pop hit (topping Billboard Hot 100 in U.S.) ten years ago, it can be the inspiration for your next trip to the used clothing store, the message is timeless. (lyrics are NSFW)
"The song's lyrics show Macklemore's esteem for thrift shops and saving money, rather than flaunting expensive items like many rappers. The song was met with universal acclaim, with various music reviewers praising its humorous lyrics and social critique. " [Wikipedia]
My outdoor propane grill is 19 years old and still works OK. I have had one bathrobe for at least two decades according to old photographs. My car is a 1999 model, as is my bicycle. I could go on. I believe this is much better even than buying someone else's used stuff.