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In pursuit of sustainable and environmentally friendly green dyeing processes, the use of laccases and natural polyphenolic compounds has emerged as a suitable alternative to the established synthetic dyeing protocols. Laccases are considered to be eco-friendly enzymes due to their use of molecular oxygen and production of water as the only by-product. The application of laccases in dyeing and functionalization of textile materials is based on their ability to oxidize a broad range of substrates including naturally occurring flavonoids. This reaction can yield colored flavonoid oligomers/polymers that have potential to be applied in textile industry as colorants. Additionally, these compounds can add novel functionalities to textile materials. Esculin, a coumarin glycoside with many beneficial biological activities, is among the substrates of laccase. In this work, laccase from Trametes versicolor was applied as a catalyst in the reaction of oligomerization of esculin to its colored oligomers enabling the in situ simultaneous dyeing and functionalization of wool fabric. The antioxidant activity of the dyed wool fabric was tested before and after washing cycle. Wool fabric showed moderate ABTS radical scavenging ability (53.32%) which remained in the same range after washing (50.78%). In order to improve the bioactivity, wool fabric was modified with chitosan and functionalized under the same conditions. The ABTS radical scavenging activity of dyed and functionalized chitosan-modified wool fabric was significantly improved, reaching an inhibition rate of 96.18%, while an inhibition rate of 80.12% was retained after the washing cycle. These results indicate that the applied process can broaden the applicability of laccase in textile industry for the production of colored and functional wool fabrics.