Brad Pitt as Will Colbert, commodities broker
New York City, Thanksgiving 2001
Episode: “The One with the Rumor” (Episode 8.09)
Air Date: November 22, 2001
Director: Gary Halvorson
Creator: David Crane & Marta Kauffman
Costume Designer: Debra McGuire
Whether it’s Ross fighting his way out of a pair of shrinking leather pants or Joey layered like a snowman in his roommate Chandler’s clothing, Friends isn’t exactly the first series that comes to mind when thinking of stylish menswear. On the other hand, the show’s female cast—particularly Jennifer Aniston as the boutique-obsessed Rachel—was a major influence on fashion of the ’90s, whether that meant an enviable wardrobe or an iconic, era-defining haircut.
From the beginning, Friends was meant to depict that period in people’s lives where we build our own “family” of chosen friends, particularly when living away from home. The first season’s Thanksgiving episode found the six leads enjoying Turkey Day together, the first time for many without their family, echoing the “Friendsgiving” traditions that would emerge among real-life groups of friends shortly after the series ended.
Thanksgiving episodes became a tradition on Friends as well, with memorable moments like the impromptu men vs. women football match in the park, Chandler telling Monica he loved her… while she was dancing with a raw turkey on her head, and Rachel’s revolting trifle that also included the ingredients for shepherd’s pie thanks to a sticky cookbook.
And then there was The One with Brad Pitt. Airing 20 years ago tonight on Thanksgiving 2001, Pitt’s guest appearance garnered plenty of excitement—and eventually an Emmy nomination—given his and Jennifer Aniston’s then-status as a celebrity power couple. I remember what a big deal it was, as my tryptophanned family gathered in my Grandma’s kitchen to watch the episode. (NBC’s Thursday night lineup had long been tied to my family’s celebrations, as I also recall speeding to a Philadelphia hotel room on the weekend of my cousin’s graduation so that we could watch the infamous Seinfeld finale.)
Pitt arrived at Monica’s doorstep as Will Colbert, one of her and Ross’ high school friends who had been bullied to the point of developing an eating disorder by Rachel. Having shed 150 pounds from his days as an overweight marching band musician, Will brings a pie that’s “no fat, no sugar, no dairy… it’s no good.”
Other than his unpopular desserts, Will shakes up the close-knit world of the six friends, putting Phoebe in heat, knocking Chandler’s already fragile ego down a few more notches, and pitting Ross against Rachel—who’s now carrying his baby—as he reveals their two-person membership in the I Hate Rachel Green Club they’d secretly formed in high school… and had used to start a wide-spreading rumor about her reproductive anatomy.
What’d He Wear?
Will arrives at Monica’s Thanksgiving dinner wearing a layered outfit that reminds me of the voguish styles of the early-oughts, from his tousled and highlighted hair to the irregularly striped shirt with its long collar draped over the neck of his sweater. (In fact, was it this very look that subconsciously influenced my own Express-meets-Banana Republic outfit for Thanksgiving 2005?)
His dark olive brown lightweight leather hip-length jacket features military-influenced styling points like the shoulder straps (epaulettes) and two patch pockets over the chest with pointed button-down flaps. The ventless jacket has set-in sleeves finished with a single button to close each squared cuff. Five dark brown recessed sew-through buttons close up the front, though the jacket gently tapers from the chest to the flat shirt-style collar, making the top a permanent open V-neck should Will wear the jacket closed (which he doesn’t.)
Will’s layered shirt and sweater recalls prevailing trends of that era, with the substantial point collar worn open and completely exposed over the shallow V-neck of his navy-blue merino wool sweater. The long-sleeved cotton shirt is striped in an unbalanced array of gray, white, shades of blue, and pale yellow.
Unlike Joey, who thought mid-meal to swap out his restrictive jeans for stretchy maternity pants, Will wears more traditional dark gray flat front trousers. Finished with plain-hemmed bottoms, these trousers have side pockets and back pockets that each have a loop to button closed. The medium rise of the trousers keeps the waistline generally covered under his sweater’s hem, though we do see his dark burgundy leather belt and its polished silver single-prong buckle in more, uh, enthusiastic moments.
Will wears square-toed Chelsea boots with uppers in a dark brown leather adjacent to burgundy, similar to his belt, with coordinated elastic side gussets.
He keeps his visible accessories minimal, aside from a bracelet with two light brown wooden beads occasionally glimpsed dangling from his left wrist, likely Pitt’s own affectation as the actor has frequently dressed his wrists on- and off-screen with everything from beach-ready bracelets to stylish Rolexes.
Anything Else of Note?
The end of the previous season had introduced the first of the Nat Nast “Rockabilly”-style color-blocked silk shirts that would be regularly worn by Chandler (Matthew Perry), a style also featured across two HBO flagship shows from being a staple of Tony Soprano’s wardrobe to the coveted “Chet’s Shirt” worn by Larry David on Curb Your Enthusiasm.
When we first see Chandler in this episode, he’s “just pretending to watch the game so I don’t have to help out with stuff” while wearing a generously sized Nat Nast long-sleeved shirt, primarily black with indigo chest panels.
Having challenged Monica to prepare a turkey exclusively for him—as few of the other friends would enjoy it—Joey takes advantage of the maternity pants that Phoebe had gifted Rachel at the start of the episode.
Joey had shown up for Thanksgiving dinner in a basic gray long-sleeved T-shirt with contrasting seams and jeans, though the challenge has him realizing that “I just gotta change my pants… what was I thinking? jeans have no give!” He reappears in the garishly patterned maternity pants, patterned in red, green, and white, with a stretchy black belly that Phoebe offered was also “great for shoplifting melons”.
Phoebe: Joey, those are my maternity pants!
Joey: No, no, these are my Thanksgiving pants!
How to Get the Look
The men of Friends aren’t particularly notable dressers (with some occasional exceptions), so their Thanksgiving menswear of oversized button-ups and maternity pants is shaken up by Will’s simple but stylish layering of seasonally appropriate clothing that offers a flattering fit.
Whether you’re dressing for Thanksgiving or Friendsgiving, these simple layers make it easy to impress… plus wearing button-ups under sweaters offer the opportunity to covertly unbutton over your belly in the event of overindulgence!
- Blue, white, gray, and pale-yellow multi-striped cotton long-sleeved shirt with point collar
- Navy-blue merino wool V-neck sweater
- Dark olive lightweight leather hip-length jacket with flat collar, five buttons, shoulder straps (epaulettes), two chest pockets (with pointed button-down flaps), and 1-button squared cuffs
- Dark gray flat front trousers with belt loops, side pockets, button-loop back pockets, and plain-hemmed bottoms
- Dark burgundy leather belt with silver single-prong buckle
- Dark burgundy square-toe Chelsea boots
While most of Will’s reactions are the result of him Looking Like Brad Pitt, making the effort to dress well is a great step in getting a Chandler-type to greet you with “I’d shake your hand, but I’m really into the game… plus I think it’d be better for my ego if we didn’t stand right next to each other.”
Do Yourself a Favor and…
Look at her standing there with those yams. My two greatest enemies, Ross: Rachel Green and complex carbohydrates.