It seems to me that you are saying that TSE matched the smoke rising
from the pipes of the lonely men in shirt-sleeves to the smoke rising
from the burning homosexuals in Hell to equate the lonely men to the
dead men.  I can't stretch my imagination that far but I do want to
pass on something that you will want to read, "Three Dante Notes"
by John Harris available at this URL:

The first part of an abstract from it is:
    JOHN HARRIS: "Three Dante Notes
    (I: Brunetto the Sodomite; II: Guido's Portrait; III: La gloriosa rota)."

    Abstract: In the first note, the author argues that not only is
    Brunetto Latini a homosexual, but also that Dante has portrayed him as
    such "with characteristically, even stereotypically, gay attributes
    and mannerisms." Among these would be the references to eye imagery
    and the manner of gazing, clothing imagery, and the use of language
    that exhibits elements of flattery, familiarity, and
    flirtatiousness. In the second note, ...

Harris definitely views the squinting of the shades with a homosexual
cruising activity.

On the translation and whether "dusk" is in there or not, "suol da
sera" is what is being translated to "dusk." "Sera" is "evening."
Here are the Longfellow and Mandelbaum translations next to Dante's

In English "new moon" is the phase of the moon in which the moon is
dark.  I got curious about this, wondering whether "nuova luna" meant
the same thing.  A literal translation does but I was wondering if
maybe it might not have meant to Dante when the light first starts
showing.  This webpage indicates that the meaning is the same:
    Some Nautical Astronomical Terms in the Western Mediterranean c1300

Due to the astronomical positions of the Earth, sun and moon that
produce the phases of the moon the new moon is not visible in the
night sky.  It would be seen during the day (if not overwhelmed by
daylight) and the times around sunrise and sunset.  All total eclipses
of the sun occur when the moon is new.  See:

    Rick Parker