No information has been given about the type of aircraft or operation, but that will help determine what's appropriate.
In particularly loud piston airplanes, I'll usually wear an earplug under a headset, which may be either passive or ANR. I like the Bose headsets, so tend to wear them in most light airplanes, often without use of earplugs.
With my helmet, I use one of two ear systems. I don't have ANR in my helmet, but good passive noise attenuation with with the helmet, liner system, ear seals, and cup inserts. I use the CEP in-ear system that places earpieces under the earcups and allows a backup hearing system as well as additional noise attenuation. I also use the Pro Flight Gear PACE in-ear system which can be fitted to a helmet or headset and uses a standard 3.5mm jack, with custom ear pieces. I use those up to 8 hours at a time and they improve not only communications but hearing protection.
In transport category cockpits, I use a Bose A20, because they're comfortable, quiet, and because at this stage in life, it's not so easy to hear communications with a good headset, even in jet cockpits. When it comes to foreign accents, I have to concentrate anyway, and it helps a lot to have the A20 vs. lightweight headsets like an Airman 750. Knocking out the background noise helps a lot.
As for having your tunes...there are times and places for it, but by and large, remember that you're not kicking it with the homeboys. You're a pilot. Any system that doesn't cut out with an aircraft radio transmission should probably be left at home.
So far as cost goes...it's your hearing and your job. You may not have hearing a few years down the line. Take care of it now. Invest in the tools of the trade. That includes a good headset. Bose, et al, have payment plans.