Right before a Monday morning meeting, Olivia, 24, showed up to her New York City office in woven flats. They were red and espresso leather braided into a basket-like pattern, fitted with a chic square toe and a stamped logo you might not notice unless you frequently shopped the brand yourself.
“What are you wearing? Send me the link!” said her boss, who pointed to the flats. Olivia hesitated. The shoes cost several hundred dollars, and she’d frequently heard her boss mention her proud affinity for Amazon dupes and fast-fashion finds.
“I was sort of embarrassed to send the link to her,” the financial analyst tells Glamour. Olivia wasn’t embarrassed by the shoes so much as what they might say about her once her boss saw the price. Still, she did send the link and her boss did comment on how expensive they were. “I really did feel judged,” Olivia says.
Objectively, Olivia didn’t do anything wrong. The shoes were appropriate for her office environment and she was excited to wear them. But sending the link to her boss made the purchase feel like a statement she hadn’t intended to make.
Which raises a strange workplace question: Can you be too well-dressed for your position? Or, more specifically, dress too expensively at work?
When it comes to shopping, we all have different thresholds of comfort. While it stands to reason that a boss may make more money than their direct reports, spending on designer pieces might not be a priority for that person. So why can it feel weird to signal to someone above you in the workplace that you’re able or willing to spend a lot on clothes?
According to Dr. Dawnn Karen, a psychology expert who specializes in fashion, it’s because clothes can communicate far more than whether you have taste. What we wear—and what we choose to spend money on—can send signals about who we are, how we see ourselves, and how we want to be perceived.
For young women at work, that can get complicated. “Better dressed than your boss”—especially when the boss is also a woman—may not be a message you’re eager to broadcast, especially when we know people make rapid judgments based on appearance. And those judgments are often influenced by context: the industry you’re in, the office culture, and importantly, seniority, gender, and race. Suddenly the seemingly petty question of who’s “better dressed” becomes a question of power—and how quickly we read it from someone’s clothes, shoes, and bags.
Not every manager is interested in what you wear, though.
Kayeigh, an advertising director, says she would never care if someone dressed “better” than her, especially a direct report. “As long as they’re dressed professionally, anything goes,” she says. “In my line of work and department, we’re client-facing, so well-dressed employees actually make me happy.”
