Which lightweight headphones sound best w/ Discmans?

Yes, I understand that "sound best" is fairly subjective, but I would still be curious to hear from folks who are more experienced than I (and maybe have better ears than I) as to which lightweight Sony headphones of the '90s - early-2000s have the best sound. I'm sure that Sony had a range of qualities that were at least somewhat tied to price, so they must've offered some better ones as well as some more mediocre ones. I'm trying to pick a pair to buy to go with the CD Walkman I'm giving my girlfriend, and would like to get her the ones that are likely to sound best, given the limitations of the platform and the open-air design. I'd also like them to look cool (but no -- I can't afford MDR-3L2-level cool).
And just to be clear: I'm talking about the "on-the-ear" types with open-cell foam, not the padded-leather over-the-ear muffs.
The contenders that I know of:

the symmetrical egg-shaped MDR-027
the "hockey-stick"-shaped MDR-004, 005 & 006
the "inverted lollipop"-shaped MDR-110 & 201
the hybrid hockey-stick & circle-shaped TRH-1
the asymmetrical MDR-14, 23 & 25

I love the looks of the MDR-70, but I'm sure they're way outside of my budget

Any opinions would be welcomed!

 

Well, I don't have any of the old Sony headphones, so I shouldn't even be commenting...

(But I always use the cheap little Koss SportaPro for casual listening to Discman etc,. The SportaPro is quite a famous little headphone for its sound. It has been in production for nearly 3 decades I believe? Not to be confused with the Koss PortaPro. Google Sportapro vs Portapro for arguments over differences.)

 

@Hyperscope - thanks for the reminder, I was going to ask the community about Koss Porta Pro but somehow never did. What are those foam pads above the earpads are for? PortaPro even has an adjuster FIRM...LIGHT.
I bought a pair hoping that the idea is similar to those famous STAX ear-speakers. But No, in my case those foam-pads never touched my skull, whatever the setting, and were just hanging in mid-air. Like a useless extra for the cheapies mentioned in the OP. My Q: what are those pads for???



And Many Thanks to @RCH - thanks to your original question I tried to remember the model of my first 'not-a-freebie-MDR-5-style' headphones. All I could remember that it was a Pioneer, and for $30 I got myself these SE-A100:

 

I'm much happier with the Sennheiser on ear neckband headphones straight quality.

I did get a Koss KPH-40, sound is pretty GOOD BUT
3 three design flaws: the metal band might be too small for some heads which lead to the plastic slider on mine to split 1 clip pin (on the left side), and the left ear the plastic mount is snap clipped it bit its easy to pop out maybe they should have glued it on. I haven't done so because I love the sound and build quality of my Sennheisers plus they have no head adjustment which infact fits my head perfectly.

 

Good question, I always assumed they were "supports" of some kind. Rip them off and ignore them. Just a junk gimmick of some sort