Jason Segel in ‘I Love You, Man’ Invented Fashion

Before sleazecore went mainstream, there was the iconic board-shorts-and-Uggs ‘fit.

by Emma Specter
Jan 17 2019, 2:33pm

“The well-dressed man is he whose clothes you never notice,” W. Somerset Maugham once said, and for years, men’s fashion adopted this maxim as something of a motto, dressing men in—you guessed it—suits, with maybe a “fun tie” or a “wild sock” for variety. Luckily, we now live in a fashion moment where men can wear couches, or capes, or sleazecore, or “little fresh meat” attire, or any other thing they put their mind to. Men: they’ve come a long way, baby!

Before King Bieber and Post Malone embraced slip-ons and Hawaiian shirts, though, there was but one messy fashion icon men could look to for inspiration. That’s right, folks, I’m talking about Jason Segel as jovial dirtbag Sydney Fife in 2009’s I Love You, Man. Men’s Fashion Week may be happening in Paris, but the only lookbook you really need is contained within Sydney's wardrobe.

Image by Benjamin Park.

From his first appearance at the open house where he meets uptight straight man Peter Klaven (played by Paul Rudd, and definitely a follower of the Maugham school of boring men’s attire), Sydney displays a fuck-it flair for fashion that just wasn’t seen in the bromance protagonists of the mid-to-late aughts. Where Seth Rogen and his Apatown ilk stuck to rumpled T-shirts and jeans in movies like Knocked Up and The Pineapple Express, Sydney approaches schlubbiness with an air of dressed-up deliberacy that prefigures the sleaze generation.

Senior Superlative: Best Power-Clash

Image by Benjamin Park.

At a certain point in the writing of this story, I will no longer be able to obscure my past, present and future crush on Jason Segel, but I do believe that said crush was launched by this specific image. Sure, the graphic-tee-under-cable-knit look is a little Seth Cohen, but Sydney makes it look like his own version of the oversized-men’s-shirt-after-sex trope; it’s as though he just shrugged it on after playing Fortnite in his boxers! But like, in a cute way!

Senior Superlative: Coziest Boy

Image by Benjamin Park.

Ah, at last, we get down to the meat of it. This look, comprised of undersized flannel, palm tree-print board shorts, and Uggs—o, the Uggs!—puts the quoi in je ne sais quoi and the “Ugg” in “rugged.” Like his puzzlingly attractive sleazecore antecedents, Sydney is beautiful in his distinct lack of beauty as he ambles through Venice, burrito in hand, walking his dog. This is a contender for greatest male ‘fit of all time because of its surprising complexity; Sydney’s three items of clothing effortlessly conjure images of Upper West Side tweens, Seal Beach surfers, early-aughts hipsters, and Ugg-and-parka-wrapped actresses smoking on set in between takes.

Senior Superlative: C.O.A.T. (Chillest of all Time)

Image by Benjamin Park.

Even at an engagement party, Sydney refuses to compromise on his signature lewk, pairing a tweed blazer with the kind of oxblood-hued, dainty scarf straight men began to embrace en masse in the late aughts. Even in 2009, post-”metrosexual” and nine years before Family Guy heroically announced it would “phase out gay jokes,” Sydney isn’t afraid to dress how he wants.

Senior Superlative: Most Dashing


A pink Lacoste! Maybe I’m overly fond of this look because I wore this exact shirt to school every day of eighth grade, but let’s not forget that in 2009, arguably peak “masculinity is a prison” years, a straight man wearing a pink shirt was—dare I say it?—bold.

Senior Superlative: Most Daring (for 2009)

Image by Benjamin Park.

Sydney makes his final appearance of the film in a suit at Peter’s wedding, cementing their bro-bond with normative apparel.

Senior Superlative: Least Improved

All hot fashion streaks must come to an end, as surely as the "marriage plot" must end in a wedding, but Sydney’s at his best when he’s rocking out to Rush in a Coltrane tee and board shorts. Jared Leto can only dream of attaining Sydney’s vibe!

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