Details wise, IEMs might be more detailed than any headphone at that price. However, it doesn't have the same soundstage

I would say for details and clarity, Iems might have an edge but for soundstage probably the headphones. I went with both at $250 each haha

I do feel that $500 and a small dongle that I can drive with is quite good enough for most IEMs. However, headphones for the $500 have yet to include the amp and DAC. The total cost of that gear will be around $200, or $700 plus or minus. Bear in mind most IEM can preform with phone or laptop just with the headphone 3.5mm jack.

I think much like speakers vs. headphones, they're just somewhat different animals.

I'm not a fancy IEM guy but I listened to someone else's Blessing2 the other day, and it still sounds like a thing you stick in your ear canal... soundstage, tactility, just not quite the same as a good $300 headphone (even as limited as that is with headphones).

@ that price point they become a question of do you like how IEM present sound or you like how headphones present sound cos you'd find great headphones and IEMs at that price point

To me, iems are better at every point. To some people over ear are better. Depends on what you like

And 500 hundred and under iem market is more innovative rn imo. So I think for most people 500 and bellow iem is a better bet. Unless Soundstage matters to you

I agree with u/No-Context5479 it is a matter of sound presentation that you prefer. I tend to prefer the headphone presentation myself but have heard many of the TOTL IEM’s and many are really fantastic but still gravitate towards headphone’s.

While tonality is preference based: The dynamic range, sense of space, and 'slam' created by a headphone can't be mimicked in an IEM.

In general: Speakers > Headphones > IEM at similar price points.

However, it depends on the listening environment. Most good headphones are Open Back. My house is old and my home office overlooks a busy street. I can't enjoy Open Back headphones due to the noise pollution. And I can't focus with speakers.

So I have a semi-open headphone that works most of the time (E-mu teak), an IEM (B2Dusk) for when its busy or I want isolation, and a pair of noise cancelers for piping in white noise when I have to focus on a high functioning task.

I have also put the nose cancellers overtop the B2Dusks for more or less complete silence.

TL:DR - Depends on use case more then anything else.

Depends heavily on comfort. Soundstage can be found in $40 Koss headphones.

Have some $15 Lenovo Thinkplus wireless buds from Aliexpress, I wear them frequently, rarely use my Sennheiser or Meze. 30x pairs for $500👍

I’d do headphones simply because I don’t like putting things in my ears.

depends on the use case, sitting at a desk i would take $500 headphones over iems for the comfort over long periods and sound stage every time, but i have a $300 pair of iems that i use almost every day at work where I'm always on my feet and every night in bed where headphones would fall off or get crushed. I love them both, but they each have their niche. If you have neither, I would split and get one of each for $250. hell, good iems are getting cheap so $150 on iems and $350 on headphones gets you into high quality stuff on both sides. I'd just browse r/AVexchange until something catches your eye lol

just sayin rn you can get HD6XX + LetShuoer S12 + Fiio BTR5 for about $450 total and be happy on all fronts

$20 Chu blows away almost any headphone of any price....