The Workplace Politics of Holiday Party Dressing

Office holiday parties are back — and all the fashion politics that come with them.

Now that most companies have found their groove with hybrid work models — often three days in-office and two days remote — there’s a renewed sense of workplace stability that is bringing the office holiday party back into focus.

All told, the office party’s role in the workplace and culture is still uncertain and evolving: Last year, The New York Times declared the office party dead, but this month, its fashion critic Vanessa Friedman reversed course, proclaiming it alive and well — complete with a list of fashion dos and don’ts.

Post-pandemic, dressing for both office and life has changed dramatically, transitioning from pyjamas and athleisure to Zoom-ready waist-up looks, and most recently, a return to officewear, albeit often more casual. Now, many people are left scratching their heads about how all of that translates into the right look for an already tricky event.

Gen-Z’s more casual take on self-expression bears a stark contrast to Gen-X’s suit-and-tie uniform, for instance. The trend of Gen-Z “corporate girlies” wearing a pair of red sequined shorts to holiday office parties has amassed hundreds of thousands of views on TikTok this month.

At the same time, the lingering effects of the pandemic may have permanently shifted how people value workplace gatherings. These rarer opportunities to connect meaningfully with colleagues — beyond day-to-day tasks and deliverables — now hold more weight. With fewer in-person meetups, the pressure to make a lasting impression — in front of the boss and colleagues — has only intensified, some experts say.

All of this, of course, is prime marketing fodder for fashion brands and retailers. White House Black Market, Chico’s, personal styling service Stitch Fix and rental platform Rent the Runway are among the fashion firms logging an uptick in interest from shoppers eager to make a style statement at this year’s company holiday parties. This week, Stitch Fix stylist Alicia Lloyd even hosted an “Ask Me Anything” session on the r/fashion subreddit, tackling the stress she said many shoppers have expressed about nailing the right look.

“About 45 percent of customers admit that they feel uncertain on what to do and what to wear this year,” Lloyd said, citing a recent Stitch Fix survey. “[They’re wondering] ‘how can I really maximize these opportunities to not only showcase who I am but also be unique?’”

Marketing the Office Holiday Party

Nordstrom, Banana Republic, J.Crew and even Amazon are among the fashion purveyors that have pushed marketing emails or created dedicated landing pages for office holiday party style this season. Overall, how big the occasion is as a shopping catalyst is a mixed bag for most fashion firms. Retailers like Nordstrom and Macy’s are vying for a slice of the pie while occasion dressing remains a key driver for Rent the Runway and Stitch Fix.

Compared to last year, however, some insiders believe the opportunity has grown.

Sales of occasion dressing items at Stitch Fix are up 175 percent year-over-year, said Lloyd. At Rent the Runway, where a majority of the customers are working women, chief merchant officer Sarah Tam pointed to a 25 percent increase in “work-to-dinner” styles in customer baskets over the past three months — which comprises versatile pieces meant for after-work dinners or dressier occasions.

Between October and December so far, customers have shifted toward “dressier” styles compared to the same period last year, she added, a trend she attributes to an uptick in holiday office parties. Leopard prints, richer tones like burgundy and brown, and skirts — especially mini skirts — have surged in popularity, even outpacing trousers.

“For a while during the holiday party season … people were a little more casual,” Tam said. “Then all of a sudden we started seeing it get dressy … we’re seeing that she’s taking it a step further and upping the ante.”

Rent the Runway has responded with a bevy of marketing efforts, launching its curated holiday collection as well as a dedicated “Office Holiday Party” landing page featuring pieces like an off-the-shoulder red Simkhai blouse and a gold sequined Marie Oliver skirt. It also debuted a few influencer collaborations and targeted ads on social media specifically for the work party, she said.

At Chico’s and White House Black Market, shoppers — WHBM’s professional women aged 45 and older and Chico’s 55-plus demographic — never fully embraced the pandemic’s pyjamas trend and always opted for more formal styles (even if mostly from the waist up for Zoom), said Lexy Onofrio, chief marketing officer and senior vice president of brand marketing at Chico’s, White House Black Market and Soma.

This year, though, feels like a proverbial permission slip to go all out, she said.

If there is a pivot for their core customer, it’s towards getting more bang for their buck — which shows up as wearing their usual nice skirt and blouse from the office but adding “shine” via one new item, like a sparkly blazer or a statement earring to dress it up for the party, Onofrio said.

From a marketing standpoint, it means Chico’s and WHBM are “not leaning in on just the office holiday party” in their campaigns but driving home attributes like versatility, durability, fit and comfort.

“The idea is ‘hey, this is a great jacket, and this jacket will take you from work to the office party, to the weekend,’” she said. “There’s definitely a value component that we need to be aware of — and going into the season, we were all a little bit more sensitive to it.”

Navigating the Office Style Politics

While there have always been detractors — the colleague whose skirt hemline raised eyebrows or the one who took the festive sweater trend too far — deciding what’s appropriate to wear to the office holiday party wasn’t always this complicated.

The pre-pandemic trend of workplace casualisation, accelerated during remote work, combined with Gen Z’s unconventional introduction to workplace culture (often devoid of in-office rituals like happy hour) and the current need to make an impression with fewer in-person moments, has created new tensions.

In a post-pandemic working world, the most notable friction lies in how different generations define “appropriate” dressing.

The best advice, said Lloyd, is simple: “Confidence is key.”

Still, each generation has its own take on the styles that make them feel confident. Safe yet expressive choices include adding shine with metallics, wearing monochromatic outfits (like head-to-toe burgundy or brown), and playing with textures like velvet or satin, said Lloyd.

For younger employees, especially Gen-Z and millennials, the office holiday party can offer fertile ground to stand out and gently explore self-expression, she added.

Outside of the holiday season, Rent the Runway has seen a rise in denim rentals, which Tam said she views as a sign that “office culture is changing” and senior leaders are more open to embrace less traditional uniforms, mirroring the flexibility seen in areas like remote work.

Stacy Berns, president of fashion and retail boutique PR firm Berns Communications Group, has been advising members of the Z-suite, a network of 20-somethings in the fashion, retail and tech industry who work with brands, on how to make the best impression at the string of holiday parties they’ll be attending. (BCG launched the Z-Suite in 2022.)

Her best advice: “Be yourself and dress in a way that lets you express who you are — but send the right message about who you are.”

Beyond avoiding overly short dresses and plunging necklines, Berns warned against behaviours like appearing disengaged, leaving early, gossiping with colleagues, or overindulging in alcohol.

“All of those things are worse than being poorly dressed,” she said.