
US model, actor and author Jeremy Meeks will not be appearing at Cayman InStyle Fashion Week this weekend after he was denied entry at the Owen Roberts International Airport on Thursday.
Meeks was scheduled to attend the annual show, which celebrates fashion, art, and music, as co-host alongside Yendi Phillips, former Miss Jamaica 2007. However, Fashion Week co-organiser Jacinth Headlam told Compass TV, at the kick-off event Thursday night, “They held him up in immigration when he landed … and because of his past … he’d done time in prison … 10 years ago, they just made an example out of him.”
Meeks, who has been nicknamed ‘prison bae’, is a convicted felon, who unexpectedly rose to fame in 2014, after his striking mugshot went viral online. He was sentenced to 27 months in prison the following year after pleading guilty to possession of weapons and ammunition, carrying a weapon in public and criminal street activity.
Acting Director of Customs and Border Control Kevin Walton, in response to Cayman Compass queries on the incident, said, “The Cayman Islands enforces its immigration laws under the Customs and Border Control Act (2024 Revision), which includes provisions regarding the admissibility of individuals with certain criminal convictions.”
Walton pointed to section 109 of the law, which outlines the criteria under which these individuals may be denied entry, and added, “While we cannot comment on specific cases due to privacy considerations, we reaffirm our commitment to upholding these laws to ensure the safety and security of our community.”
Headlam said that when Meeks landed, “they held onto him and gave us an hour to get any documents that we needed to get over through immigration, through the ministry, through government. They just needed something, and we couldn’t provide that in an hour, so they put him on the next flight back to Miami …
“It was disheartening, it was disappointing for me,” Headlam said, adding, “For me, what does it say about second chances … even though he did time 10 years [ago], since then he’s gotten baptised, he gave his life to Christ, he’s an amazing father, an amazing man of God and has changed his life around, and that’s why I always admire him and respect him.“
Headlam, who has known him for some time, recalled, “He got to play the lead in my film [this year’s ‘Love After Holidays’] and … I got to see him as a person, off the TV, him to his core.”
Calling him “an amazing man”, she said what happened to him in Grand Cayman was “disappointing”, adding, “He called me as soon as he landed in Miami. He said keep going, keep pressing forward. He believed that everything happens for a reason and he’s willing to come back. Cayman is amazing and that’s why I keep coming back, and that’s why I invited him.”
Meeks told the Cayman Compass last month, “It was an honour to be recognised at this fashion show in the Cayman Islands and to be part of an event that brings together such incredible talent.”
Disappointed
A rather disappointed Meeks posted on social media Thursday, thanking “everyone that have reached out and voiced their concern about the misunderstandings that took place in the Cayman Islands …
“I was looking forward to arriving and hosting Cayman Fashion Week, hosting InnaStar, the charity dinner, black tie gala … you know, it was going to be amazing.”
Meeks added, “I look forward to coming back once everything gets situated. I want to thank the ministry for trying to make it happen as soon as possible, but we also have to remember that what’s meant to be, is meant to be. I want to thank the agents there who tried. I will be back, and I look forward to coming to the Cayman Islands next time.”
This year’s events include the annual Red Carpet Gala and Trailblazer Awards at the Grand Cayman Marriott Resort on 11 April, with runway shows at The Ritz-Carlton, Grand Cayman ballroom the next day, featuring both kids and teens and then adults, with over 100 models.
Proceeds from Cayman InStyle Fashion Week will benefit the Creative Fashion School, a non-profit organisation “dedicated to advancing the Cayman Islands’ industry by providing education, workshops, and training programs for aspiring designers and models”, according to a press release on the events.
For more information, visit the Cayman InStyle Fashion Week website.


