The results of extensive yearly screening (2014–2020) of ortho-phthalate ester levels in textiles sent to a quality control laboratory by textile companies from southern European and northern African countries are presented. Six different regulated phthalates: benzyl butyl phthalate, di-butyl phthalate, di-(2-ethylhexyl) phthalate, di-iso-decyl phthalate, di-iso-nonyl phthalate and di-n-octyl phthalate, were measured in 4729 samples of textile materials from 10 different groups. Analyses were carried out according to the standard gas chromatography–mass spectroscopy procedure, as described by the US Consumer Product Safety Commission. The results revealed a high level of compliance with the European Union legislation (97.25%). In the group of noncompliant samples (total phthalate content >0.1% w/w), positive results were due to the presence of two or more phthalates in almost 60% of the cases. The phthalate esters most commonly detected were di-(2-ethylhexyl) phthalate, followed by di-iso-nonyl phthalate and di-butyl phthalate. In the group of compliant samples (total phthalate <0.1% w/w), the same frequency of occurrence was identified, but in this case most of the samples (almost 90%) contained only one phthalate. In addition, a growing tendency for a decrease in di-(2-ethylhexyl) phthalate levels and an increase in di-iso-nonyl phthalate and di-iso-decyl phthalate concentrations were detected throughout the study, due to replacement of the former by the latter in the use as a plasticizer. No significant differences between countries were noted with regard to the frequency or concentration of phthalates in the textile samples. The study findings contribute to advancing knowledge about the phthalate content of textiles and to evaluating and controlling the potential risks of exposure to these compounds.