Dave Portnoy divides fans with bold Kentucky Oaks outfit as Barstool chief prepares to watch his horse compete

Barstool Sports founder Dave Portnoy turned heads at Churchill Downs on Friday after debuting a flamboyant outfit for the Kentucky Oaks.

The self-proclaimed ‘El Presidente’ arrived in Louisville to watch his horse, Lovely Grey, compete in the prestigious $1.5 million Grade 1 race.

Portnoy opted for a vibrant, multi-colored floral shirt along with a navy suit for the occasion, before being spotted chatting with patrons as he prepared for the race. 

It didn’t take long for the outfit to spark a heated debate on social media, with fans split over the bold choice from the Barstool boss. 

Taking to X, one fan wrote: ‘Love the suit and undershirt tropical vibes!!’

Similarly, another user online said: ‘Looking sharp! How exciting! I hope she wins.’

Portnoy opted for a vibrant, multi-colored floral shirt along with a navy suit at Kentucky Oaks

However, not everyone was as keen on Portnoy’s race day attire. 

‘You guys look like you’re headed to a shoe salesman convention!’, one user said in response to a picture Portnoy shared on social media.

Bluntly, another fan wrote: ‘Suit too small Dave’.

Portnoy’s filly, Lovely Grey, officially drew into the field following a late scratch, moving up from the also-eligible list on Thursday.

Despite being a 30-1 longshot, the horse has seen a surge in betting interest from ‘Stoolies’ eager to back Portnoy’s stable.

Taking to his Instagram on Wednesday, Portnoy wrote: ‘My horse Lovely Grey is an extreme longshot. I don’t care. 

‘All you need is a chip and a chair. I’m proud of her win lose or draw. She’ll prob be at least 30-1 unless the Stoolies bet her down. 

‘If it was a beauty pageant she’d win in a landslide,’ he added.

The media mogul launched his ‘Go Go Greys Stable’ in 2025, a passion project focused on a unique strategy of exclusively purchasing gray horses.

Lovely Grey, a daughter of Vekoma, was acquired privately by Portnoy for approximately $75,000 after initially failing to meet her reserve at auction.