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Working in Style

On-the-Clock Cinema: 5 Films for Office Fashion Inspiration

by Liana Satenstein

September 6, 2024

Liana Satenstein recommends five films with a trove of sartorial inspiration for dressing well while you’re on the clock.

Summer has almost come to a close—and while many people on this email list don’t work in a standard cubicle (thankfully!)—there’s always inspiration to be found in the 9 to 5 look. If you’re more sartorially traditional, think: the best of Michael Douglas suiting in Disclosure or Wall Street. If you want to add a saucy effect to office dress code norms, look no further than Girl 6 and Clockwatchers. Here, see five office films to reference when adding a collared oomph to your wardrobe.
Disclosure (1994)
Disclosure is a demented mid-‘90s erotic-office movie that stars Demi Moore as exec Meredith Johnson and Michael Douglas as Tom Sanders, a boss at a CD-ROM manufacturing division. (Yes, the movie is old). This film is an example that, just because you have Moore and Douglas in a film, doesn’t make it… good. It’s a masterclass in the bizarre, with more than its fair share of quid pro quo, a potentially crippling harassment suit, and sexually insatiable characters. Though the film is completely ridiculous, the wardrobe is killer in a proper boardroom way: Moore’s blazers always have big boss shoulder pads, and Douglas’s character perpetually looks good in a structured suit.
Clockwatchers (1997)
There’s a knockout combination of looks in this indie film that stars trifecta Toni Collette as a newcomer Iris, who eats her lunch in the bathroom, Parker Posey as saucy and rude chatterbox Margaret, and Lisa Kudrow as aspiring actress Paula, along with Alanna Urbach as Jane, whose paramount quality is being engaged. The characters are temps at a stale, vacuous credit company with perhaps the worst fluorescent lighting of all offices. The crew is perpetually ignored, and they come under fire when there is a minor desk larceny. There’s also a sad attempt to unionize. The cult classic delivers some incredible fashion. Paula is flashy with many dreams woven in tiny kicky skirts and silk shirts, while Margaret veers cheeky Prada in a perpetual set of knit vests, argyle, and plaid, and Jane is saucy-bared-armed but corporate appropriate. Most interestingly, Iris arrives dumpy and layered but undergoes a tailored transformation as she becomes more integrated within her office crew. If you like the late ‘90s, this movie is an incredible resource for you.
Working Girl (1988)
Working Girl, starring Melanie Griffith as Staten Island native Tess McGill is an obvious cubicle classic. At the time, women were entering the workforce—and rising from desk to boardboard. Working Girl infused themes of inter-office relations and the mean-spirited boss with its fresh, cheeky approach. There are some good looks: bulky suits, oversized blazers, and hulking commuter sneakers. Very Balenciaga. Very perm-minded.
Girl 6 (1995)
This Spike Lee film is for those who like to lean outré in their workspaces, the people who do not fear adding a bit of zuzh to their look. The movie was a flop at the time and has since become beloved, delving into sex, gender roles, and race. The film stars Theresa Randle, as Judy, who hopes to become an actress but runs out of cash and becomes a tele-sex operator. There are big-name cameos from Madonna, who plays a phone sex madame, as well as Naomi Campbell and Debi Mazar, who take the roles of smooth-talking, horny-serving operators. Like the theme of the film, Girl 6 fashion is saucy and delicious: a waist-cinching suffocating snakeskin print blazer, a floral print knotted sleeve in a wicked shade of lime green, X-acto knife sharp suits, Campbell in a “Models Suck” T-shirt, and many old-school headsets. In other words, 1-800-WATCH-NOW, if you can find it.
Wall Street (1987)
Wall Street is for those looking to delve into classic menswear—or Michael Douglas fans who have a thing for the actor’s cut-glass birdish face. He plays blood-sucking stock market kingpin Gordon Gekko, who dabbles in insider trading and beyond. The late ‘80s money-money film is perhaps the best example of dickish masculinity in a suit: slicked-back hair, two-tone button-downs with fat collars, pleated pinstriped pants, print ties, and, of course, snappy suspenders. Take all my money!