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I'm no audiophile. I can't always tell the difference between compressed and lossless files. However, I love listening to lossless audio. I feel like I'm getting everything the artists intended for me to hear. It doesn't matter if my ears can't always hear the difference. You can test your ears here. I've enjoyed Apple Music Lossless even though it has its querks.
Let's get one thing out of the way. You can't listen to lossless over bluetooth. Lots of blogs and youtube videos talk about this, so I'm not going to go through the technical side of things.
For most cases, listening to lossless is simple. Almost every computer or device with a 3.5mm headphone jack is capable of playing back regular lossless (16-bit or 24-bit, 41,000khz-48,000khz). For devices without a headphone jack, you'll need an adapter. You've seen what I'm talking about.
These have a DAC inside that converts the digital signal to an analog one like we hear coming through the headphones or speakers. The DACs in these adapters max out at sample rates of up to 48,000khz. If you want to listen to Hi-Res music, which is just about everything with a higher sample rate, you'll need a different DAC.
There are some similar dongles that you might see on Amazon that advertise to be capable of sample rates up to 384,000khz, but I ordered a few—they don't work as well as I'd hoped. Fortunate for me, I purchased the perfect pocket size DAC about a year ago.
The Fiio BTR5 is an excellent portable DAC. It has a USB connection to connect to a bunch of different devices. It comes with a USB-C to USB-A cable, but if you are all on board the USB-C train, you can use your own USB C to USB C Cable. It has both the 3.5mm headphone jack and a balanced 2.5mm jack (I still haven't gotten into the whole balanced headphone game). In addition to being a DAC, it's also a bluetooth receiver. If you want to make some previously non-bluetooth headphones bluetooth capable, this little thing can help. You can even use it to add bluetooth to your car. (Remember, lossless and bluetooth aren't quite friends yet.) What's more, it has a clip case and built-in microphones.
So, plug this thing into your device and plug in your headphones on the other end and you are set. If you are on MacOS (and maybe even Windows or Linux), you'll need to set your audio output to the desired bit rate. But, this is were iPhones and iPads come in. These devices grant exclusive audio control to the DAC. This way, the DAC will adjust itself to the correct sample rate on the fly. Darko Audio recommends listening on an iPad.
For iPads with a USB-C port, you can connect the DAC via USB-C. If you have a lightning port, you aren't out of luck but you will need to purchase a special cable. It is not MFI certified, but it works like a charm. The USB DAC OTG Cable by Meenova does the trick and is a must have for anyone wanting to listen to Hi-Res Audio on a device with a lightning port.
Finally, headphones and speakers matter. I don't have lots of money to pour into headphones, but a friend recommended two pairs to me, both by Phillips. The Philips Fidelio X2HR Over-ear Open-air Headphones sound great and can't be beat for the money. You could also spend some extra cash and get its successor, the Philips Fidelio X3, but why spend more money?
If you want something a little less expensive, try the Philips Audio SHP9500 HiFi Precision Stereo Over-ear Headphones. It will be hard to find a more comfortable headphone, and while they don't sound a rich and full as the X2HR, they do sound pretty great. You can also try its successor, the SHP9600.
Before purchasing any of these headphones, you should know that they are open-back headphones. That means they leak sound everywhere. It makes for a wide soundstage for the listener, but fellow commuters, roommates, and family members will hear some sound coming from these.
Lastly, we come to speakers. As I mentioned previously, I don't have a lot of cash to throw down on equipment. If you are looking for a budget speaker system, I recommend the Dayton Audio B652s. They are usually about $50 or so on Amazon. If you want a slight upgrade get the Dayton Audio B652-Airs for an extra $10.
And of course you'll need an amp to run these on. There are a lot of good and bad inexpensive ones out there. If you get something like the Lepai LP-2020T, you'll be content with the value to cost ratio.
That's about it really. I've got all of these items except for the X3 and SHP9600. I love them all. I hope this was helpful to someone. Regardless of your equipment, listen to music. Music changes hearts and minds!