Why is thy apparel red…?: This second question implies that the LORD has come close enough for the prophet to ask him directly why his clothing is stained red. There is a play-on-words here since the Hebrew words for red (ʾadom) and “Edom” (ʾedom) are very similar in sound. There is also a link with the Hebrew word for “blood” (dam), which is in view in verses 3 and 6.

And thy garments like his that treads in the wine press is parallel to the previous line. The simile here indicates that the LORD’s clothes are stained red. As a first step to making red wine, a farmer extracted juice from red grapes by treading on them, and he would inevitably find his clothing stained with the juice. (In actual fact the juice from both red and white grapes is the same clear color; the skin of the red grapes is what in time turns the wine red.) The Hebrew verb for treads occurs again in verses 3 and 6. A wine press was carved into the rock, and consisted of two parts, one higher than the other (see the comments on 5.2 and 16.10). The Hebrew name for the top part is the term used here. It was a shallow hole where the farmer placed the grapes and trampled on them. The juice thus extracted ran down through a channel carved in the rock to the second hole. If this ancient custom of treading grapes is unknown in a culture, an alternative model for the line is “Why are your clothes stained like those of a person who crushes grapes to make red wine?”

Translation examples for this verse are:

• Why are your clothes all red,
your garments stained like those of the person
who treads/crushes [or, steps on] grapes to make wine?

• Why are your clothes stained red?
Why are your garments stained like those of a person
crushing red grapes to make wine?

Quoted with permission from Ogden, Graham S. and Sterk, Jan. A Handbook on Isaiah. (UBS Helps for Translators). New York: UBS, 2011. For this and other handbooks for translators see here .