Did Jesus wear premium clothes?

Psalm 22:16-18 reads as follows:

For dogs have surrounded me;
A band of evildoers has encompassed me;
They pierced my hands and my feet.
I can count all my bones.
They look, they stare at me;
They divide my garments among them,
And for my clothing they cast lots.

Here is the New Testament fulfillment of the prophecy in Psalm 22:

Then the soldiers, when they had crucified Jesus, took His outer garments and made four parts, a part to every soldier and also the tunic [Gk chiton]; now the tunic was seamless, woven in one piece. So they said to one another, “Let us not tear it, but cast lots for it, to decide whose it shall be”; this was to fulfill the Scripture:

“They divided My outer garments among them, and for My clothing they cast lots” [John evidently quoted the Greek translation of the Hebrew Scriptures, the Septuagint, or LXX].

Therefore the soldiers did these things.

According to a number of sources, the chiton (χιτών, citwn), which was a long garment worn next to the skin and under the outer cloak, was more expensive to make than an undergarment of several pieces sewn together. Perhaps a seamless chiton looked more presentable than one which was made from piecework. The salient fact in the crucifixion narrative, however, is that since the chiton was seamless, the quaternion of soldiers was reluctant to rip the garment into four pieces (which would spoil the garment) but chose rather to "cast lots" (our equivalent today of throwing dice) to see which soldier would get it whole.

As the writer of the article "The Seamless Tunic" observed:

This prophecy […] declares the commonness of divine prophecy. It shows the characteristic of earthliness that is sometimes present in the fulfillment of God’s predictions. Often He chooses the everyday deeds, the unplanned and common activities of people, as the setting and events through which His prophecies come to pass. These soldiers—having no idea that they were part of God’s designs—went about their normal work of implementing an execution. What they did was routine to them. Perhaps they joked about who got what as they divided the outer garments. When they came to the seamless undergarment, they paused to recognize its beauty; beyond that, it was business as usual. After deciding on what to do with the tunic, they gambled over it and gave it to the winner. These men were unaware that they were fulfilling a prophecy made perhaps a thousand years before. They did not know that their actions had been written into the divine record by David or that they were proving that God overrules in all things to fulfill His will.

While the seamless tunic could be considered a "luxury item" in Jesus's day, Jesus did not possess any other luxury items, particularly toward the end of his public ministry. Here is what he said to a wannabe follower:

"The foxes have holes, and the birds of the air have nests; but the Son of man hath not where to lay his head" (Matthew 8:20; cf. Luke 19:28 KJV).

Perhaps earlier in his life, Jesus may actually have owned a house in Capernaum. Here is what Gospel writer Mark tells us,

καὶ γίνεται κατακεῖσθαι αὐτὸν ἐν τῇ οἰκίᾳ αὐτοῦ καὶ πολλοὶ τελῶναι καὶ ἁμαρτωλοὶ συνανέκειντο τῷ Ἰησοῦ καὶ τοῖς μαθηταῖς αὐτοῦ ἦσαν γὰρ πολλοὶ καὶ ἠκολούθουν αὐτῷ

And it happened that he was reclining in his house, and many tax collectors and sinners were reclining with Jesus and his disciples, for there were many who were following him . . ..

As his public ministry became more and more itinerate, however, he may simply have divested himself of all earthly goods, save for the "clothes on his back," so he could travel light, as it were.

And from Professor Mark Goodacre's blog comes the following,

This may be an example of . . . accidental information, or material given away in passing, where a piece of data (here: Jesus had a house in Capernaum) is assumed and not narrated.

Furthermore, Jesus' basic needs were provided for out of the common pot, of which Judas Iscariot was in charge (see John 12:6), and a number of prominent women contributed to his support as well (Luke 8:2-3).

The apostle Paul also reminds us:

For ye know the grace of our Lord Jesus Christ, that, though he was rich, yet for your sakes he became poor, that ye through his poverty might be rich (2 Corinthians 8:9 KJV).

All the above is to say: While Jesus may have owned a tailor-made tunic, it may have been made by his mother or by another talented (perhaps wealthy) seamstress who may have been a follower of our Lord. Obviously, Jesus did not live in the lap of luxury. Moreover, he was content to entrust the moneybag to a thief, which as writer Jon Bloom observes,

Of all the disciples, Jesus chose Judas to be treasurer of his itinerant nonprofit. One is tempted to offer the Lord some consulting on good stewardship. Donors were financially supporting this ministry (Luke 8:3) and the one guy who Jesus knew was a “devil” (John 6:70) was made CFO. Now, Jesus was not ignorant of Judas’s pilfering. So why did he let him manage the money? I believe Jesus was putting his money where his mouth was. He said, “Do not lay up for yourselves treasures on earth, where. . . thieves break in and steal” (Matthew 6:19-20). So he showed us by example what he meant.