On Thursday night, Jon Stewart will sign off after 16 years at the helm of The Daily Show. We are all verklempt. It is only fitting that on this solemn occasion we take a moment to appreciate one of Stewart’s most overlooked strengths: a daring and impeccable sense of menswear. Since the beginning, Stewart’s wardrobe was provided by Armani Collezioni Made to Measure. Stewart, 40 and short, has blazed forward in daring combinations rarely seen outside Pitti Uomo and the most outré of fashion magazines. Here’s to 16 years of #menswear.
A stunning gray on gray combination with hair color to match.
Going head-to-head with President Barack Obama, Stewart courageously chose a red dotted tie for an air of bipartisanship. That Obama, though...
Here it is, your moment of zen: Stewart, effortlessly matching blue paper, white pen, a dot-and-striped tie, an off-white shirt, and a mic clip with—most importantly—righteous indignation.
One of Stewart’s most incisive acts as a fashion icon was knowing when to fold. In the case of an interview with John Kerry, the perpetually tan and dapper Secretary of State, Stewart chose sober colors and a dark tie.
Here with Bill Clinton, who rocks a lavender tie, Stewart goes clean and classic.
This look marks the beginning of the Mature Stewart: unafraid to mix patterns in complementing colors and a trademark subtle pinstripe.
Black suit, dotted tie, and stripes. Notice the avant garde touches: the asymmetrical four-in-hand tie knot and the subtle accoutrement of complementary blue paper.
Truly taking fashion to the next level, Stewart often coordinated the color of his ties with the russet velvet of his sofa and the blond wood of his desk.
A functioning buttonhole on the lapel, shoulder pads, and a hue that closely mimics the television set perched beside him. Advanced.
In his youth, Stewart preferred large collars, tiny knots, and thick ties.