Flashback: 'Mad Men' Fashion At The 2008 Emmys

Sunday night's telecast will no doubt be a big one for the AMC series, so in honor of their impending win (fingers crossed), let's take a look back at the cast of Mad Men at the Emmys back in 2008. It doesn't seem that long ago when Jon Hamm, Elisabeth Moss, and Christina Hendricks were relatively new to the Hollywood scene. But even during their first Emmys together, the Mad Men cast's star power was undeniable, while their red carpet fashion was on point.

Leading the pack was none other than Don Draper himself, Jon Hamm, wearing a classic black tuxedo and his hair slicked back. Joining him was actress and filmmaker Jennifer Westfeldt, his partner of 18 years, in a textured white column gown. Hamm and Westfeldt's breakup earlier this month means that we probably won't see them together at this year's Emmys, which is a shame given that they've been one of the most stylish couples in red carpet history.

All of the leading ladies of Mad Men have major style, both onscreen and at various award shows. That was evident during the 2008 Emmys, where Hendricks dazzled in an emerald Grecian number that was both body positive and accentuated her glorious red hair. Moss looked retro-glam in a sparkly silver gown, while January Jones channeled old Hollywood with an all-white ensemble. Meanwhile, Maggie Siff went for a more fashion forward look, wearing a cinched teal gown. As for the male cast? Solid efforts in variations of black tie.


In honor of possible and long overdue wins in the Emmy acting categories, here's what the Mad Men cast looked like at their first Emmys red carpet attendance.

Jon Hamm and Jennifer Westfeldt

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I miss these stylishly coordinated lovebirds already.

Christina Hendricks

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January Jones

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Madonna would be so proud.

Elisabeth Moss, Vincent Kartheiser, and Maggie Siff

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Good things truly come in threes.

John Slattery and Jon Hamm


Dapper and Draper. Seriously, these two deserve to pick up Emmys on Sunday night.