Different translators can render the same passage differently.
Here is this sentence in Russian: На остальных же, бывших в распивочной, не исключая и хозяина, чиновник смотрел как-то привычно и даже со скукой, а вместе с тем и с оттенком некоторого высокомерного пренебрежения, как бы на людей низшего положения и развития, с которыми нечего ему говорить.
Coulsen has taken, as do most translators, some liberties with the original in an attempt to make the translation more readable, i.e. shorter.
“The others present, including the landlord, he regarded with boredom of long habit and with a shade of lofty disdain, as if he considered them too much his inferiors in rank and education to speak to.”
I think his rendition “boredom of long habit,” IS a little awkward.
I found a translation (translator unknown) that gives the following for the same passage:
"At the other persons in the room, including the tavern- keeper, the clerk looked as though he were used to their company, and weary of it, showing a shade of condescending contempt for them as persons of station and culture inferior to his own, with whom it would be useless for him to converse."
My own translation (more literal, but also not that easy to read) of the sentence:
At the rest of the people who were in the tavern, not excepting the tavern-keeper, the retired government official looked somewhat habitually, and even tediously, together with a shade of condescending disdain, as if (looking) at people of lower status and background, with whom there was nothing for him to say.
Note: The person who made such an impression on Raskolnikov is, in the original Russian, a retired chinovnik, that denotes a minor government official in Tsarist Russia. I don’t think clerk is a good translation of this word, since a normal clerk would not necessarily disdain anyone.
So the phrase “boredom of long habit” is really, in my opinion, in Russian: “somewhat habitually, even tediously.” It would mean that the retired official has somewhat of a habit to disdainfully look at these people, whom he considers to be beneath him. He has been there before and they know him and he knows them.
Hope this helps.