Since then, O'Pry has been featured in numerous advertising campaigns and editorials for Calvin Klein, Giorgio Armani, Versace, Dolce & Gabbana, Ralph Lauren, Gianfranco Ferré, H&M, Massimo Dutti, Zara, Armani Jeans, Marc Jacobs, Emporio Armani, Lacoste, DSquared², American Eagle, Bottega Veneta, DKNY, Fendi, GQ, Dazed & Confused, V, Details, Barneys, Uniqlo, Bloomingdale's, Belstaff, D2, Arena, Diesel, Gap, JOOP!

His runway credentials include opening Versace, Yves Saint Laurent, Givenchy and Salvatore Ferragamo, closing Moschino, Trussardi and Zegna, and both for Balmain.

Other designers he has walked for include Roberto Cavalli, Louis Vuitton, Chanel, Michael Kors, and Hermès.

[10] He also appeared in Taylor Swift's music video for her song "Blank Space" (2014), as her love interest.

[11] Sean appeared on the June 26, 2016 episode "inauguration" on the HBO television show Veep playing a male intern.