The difference between listening to music using speakers or a headphone is striking.
When listening to speakers:
When listening to a headphone, each ear will receive 1 and 1 channel only. No mixing, no delay, no indirect sound.
The latter means that the room acoustics are eliminated.
More details can be found here.
You can simulate the HRTF by using a crossfeed.
Benjamin B. Bauer was one the pioneers.
A famous article by him: Stereophonic Earphones and Binaural Loudspeakers.
JAES Volume 9 Number 2 pp. 148-151; April 1961.
A crossfeed emulates the HRTF by taking the signal from one channel, EQ and delay it and feed it into the other channel and visa versa.
Your media player might have one or there is a plug-in.
A VST plug-in and a lot more about headphones can be found here: BlogOhl
A VST plug-in simulating both the HRTF and the room acoustics is Isone Pro
The same functionality as Isone Pro but now in hardware plus a little bit more.
HeaDSPeaker system consists of two main parts: tracking sensors and a DSP unit.
Tracking sensors should be attached to your existing headphones.
The provided DSP unit processes the multichannel input signal and produces a dynamically auralized stereo signal for the headphones.
HeaDSPeaker is capable of decoding 5.0 multichannel signal from 2.0 stereo sources (the analog output of modern game consoles, for example).
It can also act as a 5.1 or 7.1 USB sound device when connected to a PC or Macintosh computer.
In addition the HeaDSPeaker Home version can decode Dolby Digital and DTS encoded sound from optical S/PDIF.
Connections:

Includes Headtracking and In ear measurement
![]()
![]()

Bundled with a Stax SR-202

Manufacturers description:
In addition to its standard monitoring functions the Phonitor offers new controls such as “Crossfeed“, “Speaker Angle“ and “Center Level“. These are the essential parameters that create the width, balance and overall space within a listening field and how we recognize them coming from the loudspeaker. Crossfeed simulates the frequency dependent interaural level differences from both channels. Speaker Angle determines the stereo width caused by frequency dependent interaural time differences. Center Level regulates the balance between phantom centre and L/R stereo signals.
A review by Sound on Sound
HeadRoom has measurements of a lot of headphones.
They explain what these measurements indicate
and enables you to compare up
to four models on frequency response, distortion, impedance, isolation and
square wave response.
This won't tell you how it will sound but gives you a nice indication.

This graph tells you that Shure SE530 is louder at the low frequencies than Etymotic ER-4S.
It also rolled-off the highs much more so it will probably sound bass heavy.

Both in-ear models offer a better sound isolation than the open Sennheiser HD800

Both in-ears produces a lot of harmonics compared with the HD800.
Yes, Latin helps in case of headphones.
What kind of headphone do you have?
Oh, a circumaural one.
What the hell is that?
That’s one surrounding the pinnae.
Circumaural headphones surround the ear.
Sennheiser HD 800
Supra-aural headphones sit on top of the ears

Sennheiser HD 414
Intra-aural ends our Latin lesson.
These are placed in the ear.
Earbuds are placed directly outside the ear canal

B&O A8
IEM (In Ear Monitor).are inserted in the ear canal

Etymotic HF 5
You might conjecture up the Latin your self, one sitting on top of your head
Jecklin Float
The place to discuss headphones: