Boots.

The reason that the rich were so rich, Vimes reasoned, was because they managed to spend less money. Take boots, for example. ... A man who could afford fifty dollars had a pair of boots that'd still be keeping his feet dry in ten years' time, while a poor man who could only afford cheap boots would have spent a hundred dollars on boots in the same time and would still have wet feet.

A cute little passage from Terry Pratchett, but it holds very true if you ever need boots.

Paying for quality boot work, especially the kind that can be re-soled, is worth it for anyone who has to wear boots with any regularity.

When I first got a job that needed boots I was using an old secondhand pair. It was hell. Eventually I saved up for a quality pair and was totally worth it. I've not underspent on boots since.

As for suggestions as to what brand to go with these days for that... I'm less sure on that because I'm researching new brands myself since Red Wings are a joke compared to what they used to be. Danner still seems pretty all right these days.

Anything that separates you from the ground. So a bed, shoes, your health..

For most things in life I generally follow Adam Savage's advice: "Buy cheap tools until you know what you really need from that tool, then buy the best version you can afford."

However, when it comes to things that are related to safety or protect you from harm the more expensive/high quality they get, that advice goes out the window. Case in point, PC PSUs. You probably don't want your newly built PC to burst in flames because you skimped on it to buy a poorly rated PSU.

Kitchen knives, definitely. A good knife is a fucking godsend.

Quality underwear (once you're an adult).

A good office chair (not necessarily one of those expensive as fuck mesh ones - I hate those... But something quality).

Also, I'd distinguish between pointlessly expensive and quality.

Anything that separates you from the ground for long periods of time. Shoes, tires, mattresses, computer chairs, couches, etc…

It's almost always better to not buy a cheap sex toy. There's no regulation of the industry and many materials in cheaper toys are just straight up dangerous. Here's an article (it's NSFW, there are pictures) that goes over what materials are and aren't safe.

Custom building a computer? Don't cheap out on the power supply or you might end up with a smoke machine

I believe in the adage of, "If it sits between you and the ground, don't skimp".

Shoes, socks, desk chairs, lounge chairs, sofas, car( seat)s, mattresses...

You spend too much time in or on all of these things to be uncomfortable.

I also see posted here the Adam Savage advice of buying cheap tools first, and then upgrade after you better understand your needs. I also think that's great advice you can apply to most things. Just not the above things.

Escorts

Maybe not the expensive expensive versions but good headphones and earphones make a massive difference.

Laptops. Cheap and midrange ones defined how people perceive laptops in general: slow, hot and awful to use. Expensive ones are usually amazing, but you still have to do your research before purchasing it.

Also, cigars. Nothing comes close to proper Cuban ones.

For most things, imo, there's a middle ground. I don't think that getting the super-high end version of anything is worth it unless you truly use it enough to justify it, like for work or a serious hobby. But the cheapest option is usually junk that will do a poor job and won't last; if anything you'd save money by spending a little more for something decent, even if it's not world-class.

I'll say a vacuum.

When I was a college kid in an apartment I bought the bottom-shelf, bagged Dirt Devil vacuums and dealt with it. All the clogging, hair in the brush, cheap quality/you get what you pay for, etc. Then I moved into a house I got a mid-range Bissell to help deal with all the pet hair. The thing was questionably designed, still got a bunch of the hair in the roll, and needed regular upkeep to make sure it functioned properly. When that one went out I wasn't going to pickup the same thing even though it technically lasted for years.

I recently picked up a Shark Rotator and it sucks in the best way possible. Was it expensive? Yes. Was it worth it? Absolutely. I can vacuum my whole house knowing I'm getting as much dirt, dust, hair off the floor as possible. And I'm not going to have to deal with even half the problems the low-end vacuums have. It pivots and gets right up against walls. There is a clear window to see the brush roll from the top. It also uses fins that just don't collect hair anyway. The whole canister comes off in one easy motion and I can dump it without spilling all over the now clean floor. There are two roll speeds for hard floors and carpet. The brush roll doesn't spin when it's locked upright so it's not flinging stuff around or grinding into the carpet while I try to clean corners or the couch. And even though it's one of their "heavier" models it's still lighter than the Bissell I lugged around for years.

This is a case that better design and features comes with a price. And those design choices can directly make your life easier. So if you can afford it, go for it.

Mattress and shoes.

Both of which you use multiple hours each day, and can really break your body if they aren't ergonomic.

The cheap ones also break often, costing you more money in the long run.

Parachutes.

Power supplies and motherboards for PCs

generally if either of them go the rest of your investment goes with it. Worst case scenario the power supply damages the motherboard meaning your cheap purchase made you lose more parts.

Toilet paper. Once you rip through cheap one, you'd pay anything to buy better one in the first plce.

I bought of pair of real, honest to goodness birkenstock sandals. They were stupid expensive compared to the shoes I normally buy.

.....now I almost never wear any other shoe. They fit, they're comfortable, the straps dont cut into my feet now that they're broken in, and I can take them to the store to get resoled for way cheaper than if I had continued my pattern of buying cheap sandals and running them into the ground every few months.

Pretty much all kitchenware is worth getting the good stuff if you can afford it, even if cheap versions will work.

Probably safety-related items.

Depends on your definition of "expensive", but in general, (semi-automatic) espresso machine under $450 is probably not worth getting. Most of the time, Areopress ($30) or moka pot will make better coffee than anything under this price rage.

3D printers. Yes, there are lot of $100-$300 models out there. Unless you want 3D printer repair and maintenance to become your new hobby, just go buy a Prusa (or other well supported, full featured printer).

Funny enough, I'll never use a Ninja again after getting a Vitamix.

Nearly everything, TBH. You just gotta decide which things are important to you. Like, do you do a lot of working on cars? Spend some good money on tools - totally worth it. Tinker with something once every couple of years? Cheaper tools will get the job done, and maybe last several years at that rate.

This is true of your blender too, honestly. I don't blend stuff often and don't really care, a cheap blender is fine for me. Anyone who likes blended stuff and uses it often? Totally worth getting something really good.

Motorcycle helmets, and lawyers.

Most other things, I cheap out on -- for example for my professional tools, I buy a lot of good midrange Chinese brands. Usually quality is high and price is affordable. Same goes for phones, laptops, gadgets, and so on. I live near China though.

Niche musical instruments. A "cheap" hurdy gurdy can cost up to 2000 dollars and still sound like a bag of cats in a washing machine.

Some new recent models that are relatively cheap and sound okay exist now, but you really need to do your research.

I haven't seen it mentioned, so let me say: Outerwear. Especially if you are into snow sports, the difference between quality outerwear and cheap garbage is not just getting wet sooner. It could very well save your life if you're wearing something that will keep you dry while maintaining breathability. And nothing beats lifetime no questions asked warranty where you just hand it in and it gets repaired for you. In the long term this saves a decent penny whil also reducing your environmental impact

Same goes for base and mid layers. Cotton will kill you, and lots of cheap synthetics don't breathe well. Spend money or higher end synthetics or merino.

Lastly, don't get cheap goggles from Amazon or eBay. Heck, don't get the cheapest models from even more reputable brands. You will want your goggle lenses to provide good UVA and UVB protection, while also providing contrast enhancing features like polarization and very importantly: fog resistance. You will not have a good time if you can't see where you're going. I can't stress enough how big of a difference visibility makes for your enjoyment and safety.

Lots of kitchen tools are like that. Expensive probably isn't the right word, more like minimum acceptable quality. Restaurant supply stores are great for this: a restaurant owner won't buy the fancy brands, but they also won't get something that won't do the job right. When you get something more expensive than the restaurant supply store, you are mainly paying for cosmetics.

Food processors and mandolins come to mind: they are a pain to clean, so unless they work really well, you're better off using a knife.

Stock pots you can get thin, crappy ones from Walmart that will never let a large volume of liquid get up to temp without scorching whatever is touching the bottom. Better to save your money for something with thicker material.

Also,

• Cookie dough and ice cream scoops
• Instant read thermometers
• kitchen scissors
• cutting boards
• enameled cast iron (cheap stuff flakes off)
• measuring cups (do everything you can by weight, but when necessary, you want them made from steel, and with markings embossed on them, not painted)
• charcoal (and probably propane) grills. Poor quality craps out so quick
• probably a lot more things

For non-kitchen stuff, one that immediately comes to mind cause I just bought one is plant grow lights. Even with LEDs, you need a pretty high power output for it to be worth anything, and power output isn't even the right metric. I'm far from an expert at it, but a couple of things to look out for is if it uses a USB port, it's junk. USB (specifically type a) cannot produce enough power to be remotely useful for plants, so all those weird no-name brands you see are just annoying purple lights. Good brands will tell you the wattage, the PAR, the brand of LED used, and so on.

blender yes. Vitamix is really good

Custom golf clubs versus off the rack. Took 30 strokes off my game.

Haircuts / hair dyeing