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Gilmore Girls made the entire cast fashion icons. Whether you wanted to emulate the whimsical looks of Stars Hollow, or the celebrity glamor of stars on the red carpet, the cast of Gilmore Girls were role models. As Jess, Milo Ventimiglia was a small town boy on the show. In real life he was more experimental with fashion. He got one look from Rob Estes, who played Jess’s father on two episodes.

'Gilmore Girls' star Milo Ventimiglia poses in a suit on a red carpet
Milo Ventimiglia | Alberto Rodriguez/ABC via Getty Images

Estes was a guest on Scott Patterson’s I Am All In podcast on Sept. 18. He shared the story of the day he spent shopping with Ventimiglia, and what Ventimiglia picked out to duplicate his Gilmore Girls dad.

Milo Ventimiglia and Rob Estes were supposed to do a ‘Gilmore Girls’ spinoff

Originally, Estes was supposed to have more than just two Gilmore Girls episodes. Creator Amy Sherman-Palladino was developing a spinoff about Jess living with his father in Venice, CA. Ventimiglia and Estes even filmed a pilot for the show. The season finale of Gilmore Girls was supposed to lead into it. 

Ultimately, Sherman-Palladino decided not to move forward with the spinoff and Jess returned to Stars Hollow. Estes said that the network was only giving her a short episode order and she wanted more. So when they called her bluff, she killed the whole spinoff. But, Estes still got to spend time with Ventimiglia off-set. 

Milo Ventimiglia liked Rob Estes’ jacket 

Estes and Ventimiglia hit it off as soon as Estes arrived on the Gilmore Girls set in Burbank, CA. It led to a day trip shopping together. 

“Milo and I, it was winter when we shot it,” Estes said on I Am All In. “And I showed up with an old vintage WWII jacket. Milo has really good style. He’s tight and he doesn’t throw it in your face. It’s not about money. He just has good taste and I said to him, ‘Dude, you dress so humble but sharp.’ And he goes ‘I was just thinking the same thing about you, your boots and the jacket.’ And I was like, ‘Well, I was thinking the same about you’ and he goes ‘Well, we should go shop Melrose.’ 

Milo Ventimiglia took after his ‘Gilmore Girls’ dad 

Melrose Ave. is a famous street that runs through Beverly Hills and West Hollywood. There are all sorts of trendy shops, restaurants and hangout spots. Vintage clothing is big on Melrose, so Ventimiglia was able to find something like Estes’s WWII jacket. 

“So we took a day just the two of us, went and got food, shopped Melrose, cruised around,” Estes said. “He got a World War II jacket exactly like I had. It was really cool.”

It’s actually sweet that Ventimiglia was so admiring of a co-star’s own look. It also shows an appreciation for history, even if it’s only expressed through fashion.