The Office: Classy Christmas – Ranking Holiday Looks

If you’ve been following BAMF Style for a few years, you know I like to take a break from the enviable style of Grant, McQueen, Poitier, and their ilk to tackle a problem many of us have faced: how to dress for the office Christmas party. Given that corporate America’s closets tend to have more in common with Michael Scott than with Steve McQueen, the American version of The Office rose to the occasion to address the phenomenon of ill-fitting sweaters and ill-advised ties that seems to plague my fellow cubicle-dwellers as they don their gay apparel for the holiday season.

2020 being the year that it’s been, many staff parties have been relegated to holiday happy hours via Zoom or Teams where there will likely be a better chance of catching glimpse of a co-worker’s sweatpants than Christmas ties. For this year’s ranking of Dunder Mifflin duds, it thus feels more appropriate to settle in for Michael Scott’s vision of a more intimate holiday gathering… which also hosts its fair share of snowball scenes that would no doubt result in severe HR violations.

“Classy Christmas” aired ten years ago, the second of three episodes to be directed by Rainn Wilson. It also marked Michael Scott’s final Christmas celebration at Dunder Mifflin Scranton before Steve Carell left the series at the end of the seventh season.

Jenna Fischer, Ed Helms, John Krasinski, Leslie David Baker, and Steve Carell in "Classy Christmas", the seventh season holiday episode of The Office.

Jenna Fischer, Ed Helms, John Krasinski, Leslie David Baker, and Steve Carell in “Classy Christmas”, the seventh season holiday episode of The Office.

Series: The Office
Episode: “Classy Christmas” (Episode 7.11/7.12)
Air Date: December 9, 2010
Director: Rainn Wilson
Creator: Greg Daniels
Costume Designer: Alysia Raycraft

“Before we kick off the party, I just want to remind everyone that an office party is just that… a party,” Pam Beesly announces. “It’s not an excuse to get really drunk or confront someone or have a cathartic experience of any kind.”

Of course, this being Dunder Mifflin Scranton, there’s no way any celebration would pass free of drama, and it could be argued that Pam’s own husband Jim begins the “Classy Christmas” spiral into chaos when he launches a snowball in the face of his co-worker Dwight Schrute… who admittedly deserved it.

For whatever is going on between Jim and Dwight, it’s naturally Michael Scott that escalates the holiday drama when he learns that not only will his HR nemesis Toby Flenderson be out of the office on jury duty but Toby will be temporarily replaced by Holly Flax, for whom Michael had fallen in love two seasons earlier. Enthusiastic about Holly’s return, Michael postpones the party—which had been on the verge of starting—to be retooled as the eponymous “Classy Christmas” experience.

Thus, the double-sized “Classy Christmas” offers us back-to-back looks at how the Dunder Mifflin Scranton staff dresses for their corporate celebration, ranking the gents’ takes below based on their appropriate levels of seasonal festivity, office decorum, and overall fashionability.

Round 1

12. Darryl Philbin (Craig Robinson)

I feel good today!

Having been promoted from the warehouse to work on the same floor as the sales and support staff, Darryl quickly sees that a little more sartorial effort will be expected from him to keep up with the Dunder Mifflin Scranton holiday celebrations. Given that his former colleagues had chided him just for tucking in his shirt after his promotion in “St. Patrick’s Day” (Episode 6.19), Darryl soon sees that Christmas at Dunder Mifflin will require more than just an ecru off-the-rack cotton/poly shirt worn unbuttoned at the top to show his neutral-colored undershirt.

Craig Robinson in The Office

Let’s cut Darryl a little slack as it’s his first Dunder Mifflin Scranton Christmas party since he’s been promoted from the warehouse.


11. Kevin Malone (Brian Baumgartner)

That would be impressive if anyone knew what a comptroller was!

Arguably the most corpulent of Dunder Mifflin Scranton’s employees, poor Kev doesn’t do himself any favors in this large scarlet red sweater that manages to envelop his entire torso and essentially transforms him into a genetically enlarged cherry. Not a bad sweater on its own, this is merely an example of a man not dressing to flatter his body type.

It looks like we spy one of his usual J. Garcia “painted” silk ties with a festive red and green print, but the high V-neck covers it too much. Kevin could have better served his tie—and his midsection—by opting for a classic cardigan, perhaps even a shawl-collar cardigan, that would have added complexity and brought a degree of Andy Williams-inspired austerity.

Brian Baumgartner in The Office

At least the Santa hat adds some vertical dimension to Kevin’s outfit… though one could also argue that it’s merely the stem this giant cherry needed.


10. Creed Bratton (Creed Bratton)

Aside from his surprising turns in the second- and third-season Christmas parties, Creed tends to sabotage what could be an otherwise passable look with obnoxious ties too wild to be festive. In the first part of “Classy Christmas”, Creed stays primarily in the background, emerging only to incorrectly speculate on Holly Flax’s race and temperament. How to even describe the tie, which appears to be scattered with a large-scale print of computers alternating among red and yellow ornaments against a forest green ground, tied in a Windsor knot.

Creed Bratton and Kate Flannery in The Office

Creed reels at the Hello Kitty laptop sleeves that Kelly chose as corporate’s Christmas gift to its employees.


9. Dwight Schrute (Rainn Wilson)

Oh, my god… it’s the first snowfall of Christmas! Is that just so magical for you, little girl? Can you not wait to have a hot chocolate and cuddle up with Papa and tell him about all your Christmas dreams?

You know what, Dwight? You may be an obnoxious boor in this episode who takes a dangerous prank much too far, but you get some points for trying with your go-to holiday kit of a red-and-green striped bow tie and Santa-printed suspenders, revived from “Secret Santa” but toned down without the elf hat and ears. Granted, there’s still no sense of coordination, the belt and braces are redundant, and it’s *deep sigh* another mustard short-sleeved shirt worn with a suit… but it’s still a festive—if ultimately failed—spin on Dwight’s typically dour duds.

Rainn Wilson in The Office

Clad in red-and-green bow tie and suspenders among his usually earthy garb, Dwight makes a deal Jim will live to regret.


8. Jim Halpert (John Krasinski)

Well, it’s not a snowball, ’cause it’s only a dusting. Right?

I once resented Jim’s lack of creativity when dressing for the office—and, in particular, office Christmas parties—but, by “Classy Christmas”, the case could be made that he’s now overcompensating. No longer the laidback, scrappy, and single salesman who rotated between three worn-in OCBDs and just as many subdued ties, Jim the married assistant manager (and new dad!) has upgraded to conservative business suits and off-the-rack shirts with non-buttoning collars. Welcome changes, for sure, and he even indicates some holiday cheer in the previous season’s “Secret Santa” when he marks the occasion in a bright red tie that’s conspicuously different from his everyday attire.

A season later, and Jim now shows up at the Dunder Mifflin Scranton branch in his typical navy suit and white shirt, but his dark blue tie is printed with a wintry motif of snow falling down onto a hapless snowman at the blade. Is Jim now buying his ties from the same place as his once-resented superior Michael Scott?

Michael leaving seems to inspire some sartorial introspection, as Jim tones it down a touch with his penguin-printed red tie in the following season’s “Christmas Wishes” before eschewing holiday-themed neckwear altogether for the final season’s “Dwight Christmas”… but there’s still another classy Christmas party to go before we get to that!

John Krasinski in The Office

Jim, about to launch the snowball heard ’round the office.


7. Toby Flenderson (Paul Lieberstein)

Well, that’s hurtful talk and, uh, we’ve talked about that…

“The horrible red-headed sad sack” sticks to his established holiday tradition of a classic-patterned sports coat (this time, a light brown windowpane check) over a neutral shirt (this time, cream) and a silk holiday tie in a neatly arranged pattern (this time, rows of dancing penguins against a red ground). It’s never a particularly offensive look, and given the unabating disappointment in Toby’s personal life, it’s nice to see the banal HR rep embracing some Christmas cheer with his tie that accompanies otherwise tasteful business attire.

Jenna Fischer and Paul Liebestein in The Office

Toby makes an announcement that will change Michael’s life.


6. Stanley Hudson (Leslie David Baker)

Pam got the sugar-free cookies I like, I’m doin’ fine!

Similar to Dwight, it’s refreshing to see seasonal style on someone like Stanley who shows little enthusiasm for… well, much at all. We first saw Stanley in a Christmas sweater the previous season in “Secret Santa”, possibly a gift from his ex-wife Teri… or his girlfriend Cynthia.

The crossword-addicted salesman may have been ranked higher if he’d just selected a different tie with his outfit (or gone tieless!) as I feel like the yellow-on-green polka dots clash too much with the established navy, cream, and red in his sport jacket and alpine-patterned sweater.

Leslie David Baker on The Office

Stanley illustrates that he doesn’t need to be dressing for Florida to wear festive patterns.


5. Gabe Lewis (Zach Woods)

Kelly, I thought we agreed on fleece blankets.

Given how easy Gabe makes himself to hate, I’m surprised I don’t reserve more ire for his excessively patterned Christmas tie. Gabe may not be ready for Pitti Uomo anytime soon, but he displays some basic comprehension of coordination and fit. Aware of that attention-grabbing red tie, he keeps the rest of his outfit muted, wearing a subdued green shirt that brings out the holly in his tie. The conservative dark gray suit flatters the lanky Gabe’s 6’4″ frame with its three-button jacket and, like the shirt, refuses to compete with the tie for attention aside from a Santa pin on Gabe’s lapel that thematically unites.

While not the prize-winner for the ideal “Classy Christmas” aesthetic, Gabe’s first look in the episode

Zach Woods in The Office

Gabe offers up a pathetic wave to Erin, whom he is still surprising dating by this point.


4. Ryan Howard (B.J. Novak)

He’s rubbing his neck!

By the seventh season, Ryan Howard’s short-lived style phases have evolved to a quasi-hipster phase anchored by his rectangular glasses with thick black frames. Surprisingly, he doesn’t incorporate this into his holiday attire for the first party in “Classy Christmas”, dressing in a manner but subdued and stylish in his lavender plain-fronted shirt with a narrow dark forest green tie bar-striped in burgundy.

Mindy Kaling and B.J. Novak in The Office

Ryan excitedly decodes Toby’s not-too-subtle hints about the subject of his jury duty case.


3. Michael Scott (Steve Carell)

What every boss wants is a wonderful Christmas with no drama.

Though he’s actually dressed in a Santa suit (or at least the trousers and suspenders) for the first part of the episode, let’s enter his “street clothes” he requests from Erin in the latter act of the episode. This may be Michael’s strongest contender to date with his narrow-striped navy suit, plain white shirt, and a grid-motif silk tie with enough burgundy for a staid wink at yuletide frivolity without a dancing Santa or snowman cheapening the look.

Steve Carell in The Office

“I am dead inside.”


2. Oscar Martinez (Oscar Nunez)

Here’s a question nobody’s asking: Is this worth it?

One of the consistently better-dressed members of The Office cast, Oscar dresses for the initial celebration in “Classy Christmas” in a rich fuschia sateen shirt and coordinated paisley tie. It’s the sort of ensemble you might find on the shelves at Macy’s, perhaps with a Geoffrey Beene or Van Heusen label, but the Dunder Mifflin Scranton employees have relatively few outfitters at their immediate disposal beyond the tenants at Steamtown Mall. Even a nicer dresser like Oscar isn’t going to blow his underwhelming salary on custom-made shirts or clothes from high-end outfitters.

Oscar Nunez in The Office

Note that Oscar is using the custom mug Kelly made for him during her off-screen America’s Got Talent party earlier in the season.


1. Andy Bernard (Ed Helms)

All good, Santa!

Remember what I just said about Dunder Mifflin employees not putting too much value in high-end clothing? Enter Andy Bernard, the exception to prove the rule ever since he brought his Brooks Brothers-informed steeze to Scranton from Stamford. Andy’s first attempts to look the part for the corporate Christmas party in “A Benihana Christmas” failed to impress, though it’s worth remembering that said festivities fell right at the same time as the sycophantic Ivy grad was still trying to worm his way into Michael Scott’s good graces… and he had just the flashy tie to do it.

Four years later, Andy has come into his own, dressing more for his own preferences and truly able to put together a decent holiday party outfit that combines his personal sense of preppy style with seasonal color. Andy’s look is centered by a festive red waistcoat with gold buttons that serves as a statement piece, grabbing all the needed attention from the navy jacket, subdued graph-check shirt, and a navy tie with a woven motif of Santa playing golf, the sort of thing that might have been more obnoxious if it were more in-your-face but perfectly suited to the Nard Dog.

Ed Helms in The Office

Andy’s holiday cheer is evidently no put-on, as he can’t restrain his obvious enthusiasm during the day.

Round 2

“Holly’s coming back, and this is the most important Christmas part of my life,” announces Michael, “…so back to work!”

Michael doesn’t have much patience for Gabe’s suggestion that “I’m not sure the temporary replacement of an HR rep really warrants a party,” so the Dunder Mifflin Scranton employees’ expected celebration is postponed to give Michael enough time to round up the food, furnishings, and fashions that will live up to his theme of a “cool” Christmas. One can only imagine the pride he felt when Holly observed upon her return:

It looks beautiful in here, it’s super classy… it’s like a party for limousine drivers.

12. Dwight Schrute (Rainn Wilson)

I have no feeling in my fingers or penis… but I think it was worth it.

Perhaps cynical after he took a snowball to the face while dressed in his favorite Christmas bow tie and suspenders, or maybe just dressing for business now that he’s dedicated to the task of terrorizing Jim Halpert with snow, Dwight ignores the “Classy Christmas” direction in favor of one of his usual mustard short-sleeved shirts anchoring a brown suit and tie. Not a festive color to be seen… at least not until he surprises Jim dressed in Pam’s red cardigan and holding a bowl full of snowballs, a sight that no amount of powder to the eyes can unsee.

Change from first round ranking: -3

Rainn Wilson in The Office

Dwight establishes that there are no limits to how far he’ll go to settle the score with Jim.


11. Kevin Malone (Brian Baumgartner)

I don’t wanna get dirty. There might be girls at the party.

Kevin just can’t catch a break. He’s left his sweater at home for the “classy” Christmas, but he isn’t faring much better by just tying on a holiday-themed tie with his dark brown suit and double-striped shirt with little coordination aside from the likely unintentional semi-match of the brown suiting with the reindeer trailing Santa as he skis down the snowy slope on Kevin’s tie.

Change from first round ranking: unchanged. Kevin eleven.

Brian Baumgartner in The Office

Kevin leaves his sweater at home for the classy Christmas party.


10. Darryl Philbin (Craig Robinson)

Pick a damn tree already!

That’s the spirit, Darryl! In addition to the red satin-striped silk tie, Darryl’s slate gray shirt has a sateen cast that brings a celebratory edge. Some fit issues linger, particularly with those lower-rise trousers, but it’s nice to see Darryl putting in some effort as he brings his daughter to the office party.

Change from first round ranking: +2

Taylar Hollomon and Craig Robinson on The Office

Darryl introduces his nine-year-old daughter Jada (Taylar Hollomon) to “Santa Bond”.


9. Creed Bratton (Creed Bratton)

Creed fares a little better for the second round of “Classy Christmas”, and—once Jim’s snowball breaks the window—his addition of a gray scarf adds a surprisingly dashing wintry touch. I take no issue with his navy suit or the royal blue shirt, but I’m not wild about the, well, wild tie. Patterned with snowmen angled in every direction against a blue ground that at least harmonizes with the rest of his outfit, Creed’s chaotic tie foreshadows the famous Dwight vs. Jim parking lot showdown—or snowdown, if you will.

Change from first round ranking: +1

Creed Bratton, Kate Flannery, and Jenna Fischer in The Office

Creed picks out his own holiday treat as Jada hands out snacks from the vending machine.


8. Jim Halpert (John Krasinski)

Okay, I’m sorry, why are we discounting this whole “Woody came to life” thing so quickly?

Did Michael’s favorite tie retailer offer Jim a BOGO deal? The “Classy Christmas” dictum doesn’t affect Jim’s newfound penchant for novelty ties, though at least this one offers a cheap chuckle with its scene of Santa’s legs stuck in a chimney while snow continues falling on him against a midnight sky. Worn with Jim’s otherwise tasteful winter outfit of a dark gray pinstripe flannel suit and pale slate shirt, I consider this a slight improvement over Jim’s Round 1 look (as I guess I a least have a soft spot for smirk-worthy novelty ties), but his co-workers’ improvements overshadow his and Big Tuna stays at #8.

Change from first round ranking: unchanged

John Krasinski in The Office

Jim finds himself repeatedly victimized by a snowball-hurling prank. One wonders if the pre-Christmas tie Jim would have better dealt with this new stress imposed by his nemesis.


7. Gabe Lewis (Zach Woods)

Yet another opportunity where a blanket would have come in handy…

We see little of Gabe’s look under the raincoat and scarf he has to put on after Jim’s snowball breaks the window, but he evidently took Michael’s “Classy Christmas” memo to heart and put away his tackier tie in favor of one more subdued with a small-scaled Christmas tree motif.

Change from first round ranking: -2

Zach Woods and Ellie Kemper in The Office

Even the mockumentary’s interviewers were evidently surprised that Gabe and Erin were still dating by this point.


6. Toby Flenderson (Paul Lieberstein)

I know people are only this excited to talk to me because of the trial, but… they talk to me for a while, and maybe people realize I have something to say.

Isn’t it great to see Toby looking so much lighter and happier when he’s even temporarily freed from the confines of daily life at Dunder Mifflin! He returns for the office party in a dark green holiday sweater with a cream-and-red stitched wintry pattern, layered over the same olive mini-checked button-down that he had worn with a jacket and tie during Meredith’s impromptu (and ill-advised) intervention in “Moroccan Christmas” (Episode 5.11).

If you work somewhere that doesn’t require ties and you’re not afraid to sport what some may deride as “an ugly Christmas sweater”, an outfit like this adds some coziness when gathering around the communal punch bowl… once communal anything is a thing again.

Change from first round ranking: +1

Paul Lieberstein in The Office

Toby outlines his plan for making more friends around the office.

Exactly one year earlier, Cheyenne Jackson wore the same sweater—albeit in navy—as Danny Baker in “Secret Santa”, fellow NBC sitcom 30 Rock‘s fourth-season Christmas episode.


5. Ryan Howard (B.J. Novak)

Who’s in charge of making drinks around here? Is there a bartender…?

Like Darryl, Ryan merely livens up his daily dress with a red tie, but the improved fit of the admittedly image-obsessed Ryan’s clothes gives him a considerable edge. The red tie, detailed with a small tonal pattern, adds flavor to his businesslike charcoal pinstripe three-piece suit, which he dresses down by removing the jacket, loosening his collar and tie knot, and rolling up his shirt sleeves. As much as Ryan may have evolved into the pretentious guy-you’d-love-to-punch by now, his outfit neatly bridges the desired corporate-meets-classy Christmas party line.

Change from first round ranking: +3

B.J. Novak in The Office

Ryan offers Pam some patronizing feedback—veiled as constructive criticism—about her thoughtful handdrawn Christmas gift for Jim.


4. Oscar Martinez (Oscar Nunez)

Why would someone hug you?

Oscar’s good at dressing for a party! He pulls together another winner for the classier portion of “Classy Christmas”, wearing another colorful sateen shirt and paisley tie combination, this time with a rich indigo shirt coordinated with a dark navy tie patterned in a bright green paisley that adds a seasonal festivity. Once the broken conference room window calls for extra layers, Oscar pulls on not only his dark brown windowpane sports coat but also a Barbour-style waxed jacket.

Change from first round ranking: -2

Oscar Nunez in The Office

Oscar keeps a well-informed conclusion to himself about Angela’s date after catching his eye wandering to Ryan’s tight trousers.


3. Stanley Hudson (Leslie David Baker)

I have been trying to get on jury duty every single year since I was 18 years old. To get to go sit in an air-conditioned room downtown, judging people, while my lunch is paid for? That is the life…

Stanley improves his holiday look for the second party by opting for nearly all solid patterns that offer less potential for clashing, layering a camelhair sports jacket over an olive sweater with a bright red tie and neutral light gray shirt. The fortuitous broken window allows Stanley to tie the look together with a navy tartan scarf with white, tan, and red in the plaid that pulls out the other colors in his outfit.

Change from first round ranking: +2

Leslie David Baker in The Office

Never one for excessive intraoffice fraternization, Stanley and his martini enjoy the Dunder Mifflin Scranton Christmas party in relative solitude.


2. Andy Bernard (Ed Helms)

I don’t have kids or anything, but if my grandmother ever dies, I’m going to kill myself.

Andy, still dressing to impress! It’s a little preppier than before, and it may be a little… much… for some people’s taste, but the erstwhile Ivy Leaguer Andy (“Cornell… ever heard of it?”) still arguably the most fashionable man at Dunder Mifflin Scranton.

The Nard Dog revives his second-prize style from “Secret Santa” of a light brown corduroy sports jacket, cornflower blue shirt, and bow tie though he swaps out the cream sweater for a considerably more festive waistcoat patterned in dazzling Royal Stewart tartan plaid, a holiday favorite for its prominent red and green. Based on the fact that it’s similarly cut and styled with its five gold blazer-style buttons, now positioned to button through the right side (like a women’s garment), we can reasonably assume this is the same red waistcoat from his earlier outfit, worn reversed.

Change from first round ranking: -1

Ed Helms in The Office

Andy offers up his ‘brid—Toyota Prius Hybrid, that is—on Pam’s tree-finding mission, until realizing the irony of the car’s inability to fit a tree (despite saving trees on a daily basis) means needing to recruit his “hookup with a pickup.”


1. Michael Scott (Steve Carell)

The name’s Bond, Santa Bond. I’ll have an egg nog, shaken not stirred… classic Brosnan.

Would I actually wear this to the office? Chances are… slim. That said, the effort and consistency in Michael Scott’s “sophisticated take” on Santa as well as the fact that he finally left his tacky tie at home after wearing it for three consecutive on-screen Christmas parties give Dunder Mifflin Scranton’s proud regional manager the top spot.

Looking to make a smooth impression on his lost love Holly, Michael wears a lush scarlet velvet smoking jacket with black silk shawl collar, cuffs, and pocket jetting. The trim coordinates with his black sateen shirt and black pants, which we see have the authentic silk side stripe of formal tuxedo trousers as he has Angela hemming the bottoms before Holly’s arrival. Michael even appears to have revived “Date Mike”‘s Kangol cap from the previous season, providing for what becomes the foundation of a velour Santa hat.

Everybody loves Santa, everybody can’t get enough of the jolly old man. But that is a myth, because you know what? He is not necessarily a big fat guy with a beard! He’s not necessarily an old guy! No one knows what the real Santa Claus, gah—god!

As I mentioned, Michael’s “Classy Christmas” getup may not be right for the typical office holiday party—depending on your workplace, of course—but in 2020? Embrace the decadence.

Change from first round ranking: +2

Steve Carell in The Office

Michael chalks his Sean Connery impression up as “classic Brosnan” while preparing to have a Holly jolly Christmas, if you will.

Happy holidays, BAMF Style readers!

I hope all of you, particularly fans of The Office, enjoyed this exploration into another classic holiday episode.

The cast of The Office

Whether you’re a fan to The Office or finally just want to see what all the fuss is about, do yourself a favor and check it out on Netflix through the end of the year or on Peacock, beginning in January 2021. (If you don’t want to keep up with the streaming shifts, you can always pick up the series—or gift it to your favorite Dunder Mifflin super-fan—on Blu-ray or DVD!

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