Rudy Giuliani’s fall from grace over the last decade has been well documented. The former New York City mayor is now part of the spectacle himself, joining the growing list of presidents and political figures who get openly mocked online. Since failing to win the Republican nomination in the 20 08 election cycle, Giuliani, 81, has become one of Donald Trump’s most reliable enforcers, standing by the MAGA frontman, 79, through both of his presidential runs in 2016 and 2024. Now, a viral photo of Giuliani — paired with long-running jokes about Trump’s oversized looks — has fans jokingly wondering if there’s more behind their bond than politics alone, as the internet once again fixates on the details no one can stop staring at. Former New York City mayor Rudy Giuliani continues to be the target of online trolls who love to mock a particular photograph of his brown, laceless shoes. (Photo by Brooks Kraft/Getty Images) ‘What an EFFING Idiot’: Rudy Giuliani Loses His Cool at Mar-a-Lago Party, and What Happens Next Has People Saying He’s Hit ‘Rock Bottom’ A photo of Giuliani has surfaced on social media in recent days, igniting more mockery of the disbarred lawyer for his special footwear. He was seen posing in a navy blue checkered jacket with navy blue pants, a light blue shirt underneath, and an orange striped tie, next to His former director of communication, Christianné L. Allen Hughes. Hughes wore a black dress with a white scarf around her neck while holding a binder. Attention immediately went to their feet, as observers zoomed in on Giuliani’s brown boat-looking shoes next to her petite heels. Dozens on the social media platform came up with nicknames for his disturbing footwear, saying his brown shoes looked like “Holy orthopedic slippers,” “Steel toe dress,” or even “Super Mario joints.” View on Threads One person joked, “Now I have the Mario tune in my head.” Other social media users noted the unusual size, writing, “The square shape helps protect his toes while he’s on his knees kissing [up to] Trump.” Another poster vigorously advised, “Step the shoe game up, Rudy! You were mayor of New York City, you should have better style than this.” “That’s why he be stumbling all over the damn place. These big a– boots,” one person asserted. Fans are right to be concerned about falls as Giuliani took a tumble on a red carpet at the 2024 Republican National Convention in support of Trump. He seemed ok after he tripped and fell to the floor, as security rushed over to help him up. He appeared to be holding an Osmo camera and continued filming once he was back on his feet. Rudy Giuliani takes a tumble at Republican National Convention. pic.twitter.com/zWLiCPmP5Y— Pop Crave (@PopCrave) July 16, 2024 The viral picture of Giuliani’s laceless, coffee-colored slippers has sporadically popped up on the internet over the years. Hughes once shared the picture in an Instagram reel posted in February 2022 to celebrate their professional relationship. Giuliani and his scuffed footwear also popped up on a 2020 Reddit forum, where one person blasted the disgraced politician by commenting, “The shoes are the worst of his problems. Those shoes are bad, though.” Despite his ballot box and courtroom failures since aligning with the president, Giuliani remains a close associate of Trump. He recently suffered another embarrassing public moment in late 2025 when he struggled to record a video from inside the New Year’s Eve party at Trump’s Mar-a-Lago resort. The man once known as “America’s mayor” also led the unsuccessful effort to overturn the results of the 2020 presidential election as Trump’s personal attorney. His botched legal cases over alleged mass voter fraud made him a laughingstock and cost him his law licenses in D.C. and New York. Going from a political heavy hitter to a constant punchline symbolizes how far Giuliani has fallen since he rallied the majority of the nation after the Sept. 11, 2001, attacks. The Brooklyn native is now better known for being a ridiculous meme than being a driving force in American politics. ‘Holy Orthopedic’: Rudy Giuliani’s Oddly Shaped Shoes Have Fans Zooming In On One Disturbing Detail They Say Explains a Lot ...read more read less