[8] Verhelst struggled to find a first job and began working as a freelance pattern maker, assisting fashion icon Martin Margiela for an undisclosed Italian brand for a few years.
In an exclusive interview granted to journalist Jesse Brouns, Ann Verhelst, Patrick Robyn and Claudio Antonioli confirmed the relocation of the Belgian brand to Italy, the later stating that "Milan [compared to Antwerp] is a fashion city.
"[25] Claudio Antonioli enrolled designer Nina Maria Nitsche as "ghost" creative director of the brand, another Maison Margiela alumni, after her short stances at both Vetements[26] and Kering's own Brioni.
[27] The brand's first fashion show of the Antonioli era that took place in October 2021 in Paris, and relied mostly on denim, received mixed reviews from the international press.
[28][29][30] As for the second outing of Claudio Antonioli for the brand, in March 2022, Vogue described it, in a notably harsh review, as if "The models all looked like they were heading to a meeting with their bank managers to declare themselves bankrupt".
[31] For Sanremo Music Festival 2022, Ann Demeulemeester dressed Italian musician Mahmood,[32] who joins the list of the brand's legends alongside Patti Smith and PJ Harvey.
In December 2022, to the industry’s surprise, Claudio Antonioli named the social-media savvy Ludovic de Saint-Sernin as creative director of Ann Demeulemeester, only to part ways with him less than six months later and after one single collection.
[33] In June 2023, Antonioli then appointed as the brand’s fourth creative director in less than three years, Stefano Gallici, a former intern at Haider Ackermann and one-half of a duo of Italian DJs called the Nausea Twins.