[How about vintage Preamps?]
It is an interesting question. I only have one preamp with a headphone output (Hafler DH-110) and it can drive high impedance phones. I never thought that the sound from the headphone jack was lacking, just not very engaging.
You will find that most vintage tube preamps do not include a headphone output, as they are designed to provide buffering (impedance matching) and gain (voltage) but little in the way of current capability and therefore power to drive headphones. The classic Marantz 7C all-tube preamp does not provide a headphone output, while solid-state Marantz 7T (The "T" stands for transistor) does provide a headphone jack. Originally these two Marantz products were sold at the same retail price. Today, however, a nice example of a model 7C preamp will cost more than $2,000 US, while the 7T can be purchased for under $300.