Yes I believe there is a duel transitory meaning in Gen. 49 with regard to two separate terms being used for His vesture being stained in a different manner, "garments" in wine, and "clothes" in the "blood of Grapes" in the same sentence that also can be seen as transitioning to Isaiah 63 .
I believe that Gen49
"he washed his garments in wine" is reference to wine being symbol of His Blessing.
"he washed his garments in wine" He shed the wine of His Blood of His own volition for Blessing.
This was the young lion's whelp Jacob first mentions whose garment's will be stained with the wine of his own blood, shed for Blessing.
Jhn 19:2
And the soldiers platted a crown of thorns, and put it on his head, and they put on him a purple robe,
Luk 23:34
And they parted his raiment, and cast lots
But notice in the future detailing of the prophesy by Isaiah 63 the roused up Lion of the Tribe of Judah, full of power, has His "garments" not stained with the Blessing of wine of his own blood, but with the blood of His enemies :
"...and their blood shall be sprinkled upon my garments," Isaiah 63
Corresponding with the second mention of Jacob in the same verse of His clothes being stained differently with what to me is much more a symbol of vengeance , and of a winepress being trodden in anger, the
"Blood of Grapes"
" ...and his clothes in the blood of grapes:" (Gen. 49)
Bringing in Genesis 49 is very useful in noting the transition taking place in Isaiah 63. Particularly since, as you're pointing out, there are two sources of blood on the garments of the personage in the crosshairs of Isaiah chapter 63.
Isaiah 63 starts out with the person already having a bloodstained garment seemingly prior to the killing. When in verse 2, he's asked why his garment is already blood-stained, he doesn't respond that he's just killed people, that comes latter, but that he's tread the winepress alone (to provide himself salvation). Similarly, in numerous messianic-passages throughout Isaiah, Messiah asks why it is that when he came no one listened to him, why did no one help him, to which he responds that for that reason he provided salvation alone, singularly.
3 I have trodden the winepress alone;
And of the people there was none with me:
For I will tread them in mine anger,
And trample them in my fury;
And their blood shall be sprinkled upon my garments,
And I will stain all my raiment.
4 For the day of vengeance is in mine heart,
And the year of my redeemed is come.
In verse 2, when asked why his garment is bloodstained (already), he relates it to securing salvation singularly. He then predicts that these same bloodstained (already) garments will get splattered with the blood of his enemies.
3. פורה דרכתי לבדי ---I alone have trodden a winepress, unaided by the merits of Israel (Radak). Although God often acts by virtue of Israel's meritorious deeds, the scale of ultimate Redemption will transcend Israel's merit, requiring Him to act alone.
The Milstein Edition, the Prophets, Isaiah 63:3.
Ultimate salvation was provided alone, on a lonely hill, by Messiah, singularly. That's the blood that's already on his garment when he comes (returns) to slaughter his enemies just prior to the beginning of the Kingdom of God.
13 And he was clothed [already] with a vesture dipped in blood: and his name is called The Word of God. 14 And the armies which were in heaven followed him upon white horses, clothed in fine linen, white and clean. 15 And out of his mouth goeth a sharp sword, that with it he should smite the nations: and he shall rule them with a rod of iron: and he treadeth the winepress of the fierceness and wrath of Almighty God. 16 And he hath on his vesture and on his thigh a name written, KING OF KINGS, AND LORD OF LORDS.
Revelation 19:13-16.
In this parallel passage from the New Testament, Messiah comes wearing (already) a vesture dipped in blood (his own), that is, prior to the destruction of the enemies of God (which follows). The transformation between Messiah son of Joseph, who's made to wear his own blood, versus Messiah ben David, who gets the blood of his enemies splattered on his already red garment, is, perhaps, a New Testament sort of transformation of Messiah, even though hidden elements of it are found throughout the Tanakh. If one reads the Jewish commentaries on Isaiah 63, many of them see veiled (and not so veiled) references to the destruction of the temple at Jerusalem.
For when I called, no one answered, when I spoke, no one listened. They did evil in my sight and chose what displeases me. . . Hear that uproar from the city, hear that noise from the temple. It's the sound of the Lord repaying his enemies all they deserve.
Isaiah 66:4 & 666.
Judaism's interpretation of the slaughter that precedes the Kingdom age doesn't typically include Jews and wayward Israel in the pre-Kingdom destruction wrought by Messiah. Nevertheless, Genesis 49:8, implies that the enemies of Judah are of his own household, his brother's who praise him but are nowhere to be seen when the time to secure salvation arrives. In Isaiah chapter 66:4 (just 3 chapters removed from chapter 63) we hear of Messiah calling, and no one answers, speaking, and no one listens. The result (just two verses removed, verse 666, as it were), prophesy what occurs when, just 40 years removed from the events of 66:4, the Romans destroy the temple. In Isaiah 666, its the temple in Jerusalem that's being destroyed, and Israel who are in the crosshair of God's judgment.
Versification isn't canonical (it's not part of the signature text), nevertheless it's ironic, at least, that the anti-Christ, who Jesus said Israel will happily welcome after having shunned him, is said to destroy the temple by placing a statue of himself in the most holy place (ala Antiochus). That the prophet Isaiah's prophesy of the destruction of the temple would include its two-fold transformation, that is that it would be related to AD 70, and also the tribulational temple, and that both destructions would be seen in one verse, 666 (requiring a vertiginous Gestalt-shift) is at least astronomically peculiar.
John