Casey DeSantis' Worst Outfits All Have One Major Mistake In Common
First lady of Florida and Governor Ron DeSantis' wife Casey DeSantis seems to be channeling former FLOTUS Jackie Kennedy, possibly as a ploy to make herself look the part of a future White House inhabitant. In the media, she's portrayed as a devoted wife, a mother of three, a cancer survivor, and a former TV journalist. And her fashion choices have acted as a supporting character, making her look pulled together and aspirational, but not condescending. She's also on-trend with her Republican hair (here's what it's all about and the worst offenders). But there's one fashion element that has repeatedly featured in some of her worst outfits: her gloves. And we're not talking woolen mittens in the winter. Florida's first lady loves to lean into retro-style formalwear gloves.
DeSantis has worn them throughout her husband's governorship, including at a White House state dinner in 2019, at her husband's January 2023 swearing-in when she paired white gloves with a mint-green gown, per Facebook, and again two months later with a retro-style pink dress at an official event. She wore the same pink dress in January 2025, this time paired with black gloves. While some love the old-school glamour she brings to her role, others have had enough. One Facebooker wrote, "OMG the prom dress and black gloves. She keeps trying to imitate Jackie Kennedy and fails miserably." Meanwhile, an X user wrote, "Homegirl thinks she's Jackie O, doesn't even get the glove lengths right, she's wearing semi-formal evening gloves with a midi formal day dress, absolutely not."
Casey DeSantis' gloves need more balance to work
It wasn't that Casey DeSantis missed the mark by wearing gloves. Au contraire, they've been on-trend again in the mid-2020s, and fashion-goers are still sporting them at fashion weeks into 2026. Where DeSantis failed was in what she paired them with. By channeling Jackie Kennedy in retro outfits paired with gloves, like the pink tea-length dress she wore in March 2025, she looks costume-y and outdated. Compare that to May 2023, when she was pictured campaigning in a cornflower-blue midi, sans gloves, and looked sophisticated rather than over-the-top. After all, one of the ways to embrace the dramatic opera glove trend is to pair them with modern elements to avoid looking stale and contrived.
Street stylers are demonstrating how to pull the look off by pairing them with textures and layers. The texture can be in what you pair your gloves with or the gloves themselves, whether they're lace or denim — consider it one more way to stylishly wear denim beyond jeans. And rich colors like merlot or green leather, which style icon and envelope pusher Greta Lee wore on the SAG red carpet in 2024, are another way to avoid looking stale like Casey DeSantis. Also, styling gloves with a few bangles on top brings this look to the 2020s, safely out of the 1950s and '60s.