Best Dressed at the Bet Gala
- Caroline Morales
- May 7
- 5 min read
What a day Monday was. I love the Met Gala as you saw from my last blog, but I am so glad I got double the fun with the 1st annual Bet Gala. First of all, what an epic intro, I always love seeing the fun intros for Barstool events. I loved seeing all the Barstool employees looking spiffy when we're used to seeing them in casual work clothes. Obviously we got a glimpse of it awhile back at the 20th anniversary awards show, and clearly this doesn't touch it, but I do love the combo of black tie and a theme.
The theme of the Bet Gala obviously was gambling, and I think there were some pretty fun takes on the theme at the event. I loved the announcing crew of Dave, Fran, and Clicky, but the only person that I think would've been a good addition to the red carpet is Kate. I love her dry humor and quick wits, I think she would have done really well with Nick on the carpet. And just like the Met, I wish we got more of a look inside the gala part.
Anyway, let's get into my best dressed
Rico Bosco
I'm sorry but I had to include at least one of the money suits even though Dave was not a big fan. I am also sorry Dana that I had to pick Rico, because of the full money suit, hat, and glasses. It just looks more black tie money suit (lol) than Dana's did. But yeah, starting off not so strong with Rico.
Steven Cheah
I hate to say it but I really liked Steven Cheah's outfit. I think the classic tuxedo is great. At first glance you may not think he dressed to the theme, but he has a subtle nod to gambling with the purple accessories, the color of Trust the Data. I think he looked great, but I do think they created a monster during the film festival with the round sunglasses; at least these ones are a normal size.
Big Ev
I love a classic suit with a fun inside. I think Ev looked great. I wasn't expecting him the make the list, maybe the honorable mentions, but then he whipped open the jacket. Hell ya brother. I love it. I love that its props. I love that he's got the paper bet slips on hand. I love the classic all black gambler sunglasses. Well done.
Wallo and Gillie
Nothing crazy with their looks. A well fitted suit and their trademark big logo hats. Nothing to exciting but they look great with the right amount of fun. The only reason they are this low on the list is because I learned while watching that they own this brand. I had no idea, but I knew there was a reason I loved them. Good for them and I think I'll need to get me one of those hats.
Frank the Tank
Frank looks incredible. I cannot believe how much weight he has lost. He is truly an inspiration to so many. He looks great in the suit. He didn't follow the theme too much but gave a nod to it by wearing blue and Mets bowtie for his bets. He also had custom tank cufflinks. Incredible. No notes.
Liam Blutman
Love it. I love Blutman so much. He is just the main character of everything even if he is just sitting there not speaking. Ballsy as fuck for him to wear fur in the desert but it was totally worth it. Incredible look. Not really to the theme except that he looks like a pimp that lived in the casino in the 70s. I guess that is very to theme so I take it back. Good Work Liam. A+.
El Pres himself, Dave Portnoy

I loved his custom suit. That color blue looks great on him. I really liked the dice on the front pocket. Also the custom touch on the back with his new logo for his stable, Go Go Greys. Great look especially coming right after the Derby. I also think Dave can do no wrong #TeamPortnoy for life.
Brandon Walker
Brandon looked fantastic on the carpet. I 1000% agree with Fran that this color is perfect for a blonde like Brandon. He looks incredible. I love the fun pattern of the jacket and the plain bottom. I didn't think it really went with the theme, but then he said the blue was for the bets he took that night so I cannot complain about that. Thank you Brandon for just looking great, I hope you got a yes from @GreatHairDayBFW
Feits
When Feits first walked up to Clicky on the carpet, I thought for sure he was going to be my best dressed. He looked fan-fucking-tastic. He followed the theme perfectly without being tacky. I loved that shirt so much. The fit of that suit is incredible and is definitely one of those suits that not everyone can pull off but Feits definitely can. I loved it and I have nothing else to say.
Big Cat
People in this instance is me. Big Cat was definitely the best dressed of the night. Absolutely Incredible. No Notes. I love the all black custom suit with the simple black shirt underneath and the patented Barstool Sports Advisors glasses. I love everything about it. The 16-0 on the pocket spot is amazing. You all already know how I feel about the fun inside of a suit jacket and this one absolutely won. All of his winners. Perfect. The best dressed and the best take on theme. A++++
Now for my honorary mentions just because
The Girls!!!!!!!
Obviously I couldn't forget about the girlies!!! I didn't put them in the top 10 because it just wouldn't be fair for the boys. The girls slayed the whole night. I loved all of their outfits and have no complaints about any of them. They all looked gorgeous so enjoy the pictures of them from the night.




Queens. All of Them.
Hanks Cowboy Comment
I think Hank would have gotten yelled at for his outfit if he didn't make the comment, "Cowboys were the original gamblers." I truly think he thought the theme was Arizona, especially when Feits mentioned it shortly after. I think he messed up the theme and had to come up with a good line to say to Dave and he did just that. Props to him.
Big Cat and PFT's Kidney Stones


Thank you Jerry O'Connell for this wonderful moment. Truly the last think I was expecting to make an appearance on the red carpet. Also Jerry's look is iconic in its own way so it was just too hard to add it to the top 10.
Thank you for coming, I look forward to next year's Bet Gala.
Comments