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12 Photos of Milo Ventimiglia That Sum Up the Early 2000s

These take Gilmore Girls nostalgia to another level

Sadie Gennis

Gilmore Girls is back, giving longtime fans a major dose of nostalgia for that golden era known as the early aughts. This was a period dominated by boot-cut jeans, unnecessary fedoras, iMacs, greasy hair drapes and, of course, the peak era of the WB.

But for Gilmore Girls fans, no one person encapsulates this time more than Milo Ventimiglia, the actor who helped shape many Millennials' adolescence through his unforgettable portrayal of brooding bad boy/bookworm Jess Mariano.

Both onscreen and off, Ventimiglia was a walking, talking poster boy for the early 2000s. He had the hair, the clothes, the unfortunate accessories and the most Y2K-era friends of all time. Photos of Ventimiglia during his Gilmore Girls tenure are like a perfectly preserved time capsule of an era when Paris Hilton was still queen, Sidekicks were all the rage and every kid wished they could have the fast-talking, witty banter that Rory shared with Lorelai, and a bad boy of their own to steal their books and write notes in the margins.

Gilmore Girls: A Year in the Life is exactly what we need right now

In honor of Gilmore Girls' return, let's take a little journey together and look back at the early 2000s with Ventimiglia as our trusted guide.

1. Jess Mariano's very first appearance truly had it all: a puffy vest, a camo shirt, an oversized digital watch and a frickin' bracelet. What more could we have asked for? (A: A Von Dutch hat, perhaps?)

Milo Ventimiglia​, Gilmore Girls

2. We don't know which is more 2000s: his Hives t-shirt or the fact that he wore it to the premiere of Divine Secrets of the Ya-Ya Sisterhood.

Milo Ventimiglia
Frank Trapper/Corbis via Getty Images

3. Ventimiglia and his Gilmore co-star Alexis Bledel were one of the It couples of this era. One can only hope their IRL relationship was a little less turbulent than Rory and Jess'.

Milo Ventimiglia and Alexis Bledel
Craig T. Mathew/Mathew Imaging/FilmMagic

4. When Ventimiglia wasn't hanging out with his WB girlfriend, he was hanging out with other super hip WB stars like Amanda Bynes.

Amanda Bynes and Milo Ventimiglia
Matthew Peyton/Getty Images

5. If the 2000s could be summed up in three words they would be: Too. Much. Denim.

Milo Ventimiglia
Vinnie Zuffante/Getty Images

6. Where do we even start with this one? The hat? The shirt? The fact that this was taken at a launch party for the T-Mobile Sidekick? Frankly, it's all a bit too much for us to handle right now, so let's just move on.

Milo Ventimiglia
Vince Bucci/Getty Images

7. Nothing says "punk" more than wearing a t-shirt that literally says "punk" over a long-sleeved shirt.

Milo Ventimiglia​, Gilmore Girls

8. Guys, we don't know if Ventimiglia has made this clear enough already: he was super into the Volcom trend, and he really wanted you to know that.

Milo Ventimiglia

Milo Ventimiglia

Ron Davis/Getty Images

9. Who decided sleeves should be three inches too long in new millennium? And how much do they regret that decision now?

Milo Ventimiglia​, Gilmore Girls

10. Milo Ventimiglia. Jamie Kennedy. The 2003 Teen Choice Awards. Enough said.

Jamie Kennedy and Milo Ventimiglia

11. Early modeling photos from the early 2000s are truly the gift that keeps on giving.

Milo Ventimiglia
Ron Davis/Getty Images

12. To have been a fly on the wall at this Halloween party with Ventimiglia and Shane West...

Milo Ventimiglia and Shane West
John Sciulli/WireImage for The Rose Group