Office Wear: A Tale of Two Generations

Boomer women stick with the Murphy Brown look. Millennials see nothing wrong with a little skin

Now that it's summer, the generation gap in the office is as obvious as the almost-bare feet flip-flopping down the hallway. Baby boomer bosses, in their Hillary pantsuits, eye entry-level Millennials with bemusement at best and disdain at worst: Why the tight tops and skinny jeans? Twentysomethings shrug off the scrutiny: It seems parents and bosses just don't understand.

Sallie Gaines represents the older generation. A senior vice-president in the Chicago office of public relations agency Hill & Knowlton, Gaines, 55, is no fashionista. "I am an old, fat, white woman," she announces. "I am not stylish." She wears dull-colored suits most days, tweed jackets on occasion, and on casual Fridays, she sports twin sets, Norm Thompson black jeans, and earth-tone flats. She tucks her light brown hair neatly behind her ears.

But if Gaines dresses without flash, she does it consciously. She says she came of age at a time when women wanted only to blend into male-dominated workplaces (, 6/19/08), not call attention to their femininity. She says her dress also conveys to clients and co-workers that she is a professional at work (, 10/23/07). It's no wonder then that she is unnerved by women who drift into work wearing bright tops or fitted dress pants. Or that she is downright shocked when they wear even less, baring bellies, toes, or tattoos. "We banned flip-flops here two years ago," says Gaines. "I still can't believe we had to tell people not to wear them."

Does it Pay to Look Masculine?

Like others in the younger generation, Anne Mahoney considers herself a hard worker who wants to be taken seriously. But she is also not afraid to bring a little sass to the workplace. A short, freckle-faced brunette who started as a junior account executive at Hill & Knowlton two years ago, Mahoney, 25, shows up for work most days in black dress pants from Limited or Express, a bright, fitted shirt—purple, teal blue, and kelly green are her favorites—and heels. High ones, like her pair of three-inch orange Tommy Hilfigers. "Hopefully, older women see us as having more freedom in what we wear, and hopefully, they don't hold it against us," she says.

Gaines says Mahoney's generation never has had to worry about sexism in the workplace, so the women think nothing of wearing clothes that highlight their bodies. Mahoney's response? "I watch old Murphy Brown shows and see the big shoulder pads and the women dressing more masculine, and it is so off-putting. I don't think that kind of fashion proves anything today. It doesn't mean you are more serious. People feel more comfortable dressing in tune with their personalities."

As temperatures rise, Mahoney says she'll ditch her black dress pants for short-sleeved cotton summer dresses in sea green, with a Jones New York (JNY) white cardigan over the top. It's a good thing she mentioned the sweater. Gaines on bare arms: "Nope." Mahoney won't be wearing stockings, however. "I think that really is a generational thing," she says. "I would never wear nylons." Gaines will, even if she hates them. "You don't want to flash skin."

"I'm not saying join a nunnery or wear a burka," says Gaines, whose summer wardrobe is black or neutral-colored suits from Lands' End, "but come on."

See our slide show on generational differences in dress (, 07/06/08).

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