First things first: Maxing out your budget for headphones only makes sense for folks who really love music, because with a great headphone you'll get more out of it. You'll hear "deeper" into the mix, details the band and the engineers sweated over for weeks or months, fine-tuning the sound of the music that was always there, but unheard by you.
If up to this point you've just bought "disposable" headphones that suffer premature deaths, and replaced them with another cheap headphone, the cycle repeats, and you live with one crap headphone after another. Maybe it's about time to break the cycle and buy a better-sounding headphone from AKG, Audeze, AudioQuest, Beyerdynamic, Bowers & Wilkins, Focal, Grado, Koss, MrSpeakers, Oppo, Sennheiser or Stax that might last 10 or maybe even 20 years, and deliver amazing sound along the way.
These headphones are usually a lot more durable than the cheap stuff, and most high-end companies service their out of warranty headphones for reasonable prices. Koss goes the extra mile an offers lifetime warranties on almost all of their headphones for the original owner.
Sure, the best headphones are expensive, but since they're built to last you might want to consider buying a used one on eBay or Audiogon, and save a bundle. Many high-end companies sell replacement earpads for their older models.
I know lots of folks who still use their 20-year-old Grados all the time. I cherish my original Grado RS-1 headphones; they're more than 10 years old. I recently bought a 45-year-old Sennheiser HD 414 headphone from its original owner, and it still sounds great!
Some people use the excuse that they lose headphones, and that's why they never get really good ones. I'm sure it happens, but do you only use the cheapest smartphones or cameras because you lose them on a regular basis?
I'd love to hear from folks who took the plunge and bought a great headphone; go ahead and share your experience in the Comments section below.