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How to dress for every stage of your career

We asked a variety of experts to share their advice for what to wear if you’re entry-level, just got a promotion, or are switching careers.

How to dress for every stage of your career
[Photo: Anton van der Weijst/Unsplash]

There are a lot of unspoken rules in the workplace, and one of them is often how to dress. Today, fewer than half of American workplaces have an office dress code, according to a recent survey by Simply Hired. But even among companies that have published guidelines regarding apparel and accessories, the parameters can be rather opaque.

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For instance, in a memo to staff about its new, more relaxed dress code, Goldman Sachs stated: “Goldman Sachs has a broad and diverse client base around the world, and we want all of our clients to feel comfortable with and confident in our team, so please dress in a manner that is consistent with your clients’ expectations.” Leaving employees to use their best judgment is the reason many offices allow a vast array of clothing choices, from jeans and sneakers to suits and heels.

What we wear to work does make a difference, even in an era of anything goes. In a recent study by Robert Half, the majority of professionals (86%) and managers (80%) surveyed said clothing choices affect someone’s chances of being promoted. And 44% of senior managers said they’ve had to talk to an employee about their inappropriate attire, while a third (32%) have sent staff home based on what they were wearing.

Throw in the fact that most people will cycle through several different careers during their working life, and the daily conundrum of what to wear becomes far more fraught than ever.

Luckily there are experts to guide us through best practices for how to dress at every stage of our careers. Here’s what they told us:

Entry-level to early career

When you are starting out, making the right impression is crucial. However, Alexandra Howell, assistant professor of fashion merchandising and design at Meredith College, says the old adage “Dress for the job you want” is kind of outdated in 2019.

Howell notes that if you’ve been hired, you’ve already spent time in the office and know at least a little bit about the company culture, which includes some expectations regarding what’s appropriate to wear to work there.

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“Whether they require streetwear, business casual, or even formal,” says Howell, “I recommend dressing up or more formally when you first start out.” You have to keep this within reason, she cautions. If, for example, during your interview, your manager was wearing jeans, sneakers, and a hoodie, “it may be overkill to show up in a full suit [regardless of your gender], but at the same time simply replicating what your boss was wearing can seem like an overstep.” That’s why Howell advises sporting business casual. She says fitted dress pants and a button-down shirt with loafers for men and a pixie pant with a comfortable blouse or sweater and flats for women are generally safe bets. “As you become more comfortable and familiar with the culture of the company, you can reassess your wardrobe,” she says.

Dana Goren of Hibob also notes that it’s important to remember that as the youngest or newest employee, you are beginning to establish yourself and must show that you are prepared for whatever tasks you are given. “Even if you are productive and a high achiever, looking disheveled or inappropriate can undermine your credibility and cause others to doubt your abilities,” says Goren. Not only do others size you up in seven seconds or less, but research suggests that someone can determine whether or not they think another person is trustworthy within one-tenth of a second, she says.

That’s why she says, “If you work directly with clients, take care that you’re dressing in a way that’s appropriate to meet with them, as their office dress code may differ from yours.”

If you’re still struggling to figure out what’s appropriate, Scott Young, managing director of client delivery at CultureIQ, suggests simply asking the recruiter or HR leader. “You can certainly deviate in a dress code-free office,” he says, “but you want your new colleagues to focus on your performance, not your appearance.” Young says it’s perfectly appropriate to be more formally dressed than everyone else—at least to start. “Most people will accept that you are still in the post-interview process and want to put your best foot forward,” he says. “But being underdressed may signal that you don’t care about the job.”

Moving up the ranks

Yes, your dress code should change if you get promoted, says Laura Handrick, a career and workplace analyst at FitSmallBusiness.com, “but only slightly—in subtle ways.” Handrick says clothing choices help establish authority over your former peers. For example, if your team members wear vintage band T-shirts, she suggests wearing a polo shirt instead.

“Senior leadership is watching,” she says. “They’re assessing your ability to contribute at higher levels, and likely with more clients, vendors, executives, and investors.” So, if you continue to dress like your staff, you’re essentially telling your leadership team that you align better with workers than leaders, says Handrick.

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Keren Kozar, who oversees human resources and hiring at January Digital, takes the opposite approach. She believes that if you’ve been dressing for the job you want the whole time you were an individual contributor, you may not need to change much. However, “if the transition requires newly added face time with clients,” she says, “make certain to dress for the client environment. If this means keeping a blazer or change of shoes at the office for client-facing meetings, do so.”

Patricia Brown, chair of Virginia Commonwealth University’s Department of Fashion Design and Merchandising, believes it’s always good to keep reevaluating what you wear to work. “If suits are appropriate in your work environment, then maybe a newer suit or two would be warranted,” she says. Or you could add a jacket, topper, or, in some cases, a refined cardigan to elevate an existing outfit. “A ‘third piece’ or jacket adds polish, a little bit of perceived authority, and often that extra element of style,” she says. Bonus: They double as extra warmth when summer air-conditioning turns your office into a meat locker.

Second or third act

Really, the advice for first-time job seekers still applies no matter your age or career stage, says Young of CultureIQ. More than half of U.S. employees say they feel comfortable wearing jeans in the workplace, and over one-third say the same thing for sneakers, according to the same SimplyHired survey. “That is something to keep in mind if you are an older worker coming from a more rigid, formal, hierarchical workplace into what is likely to be a less formal one,” says Young. While erring on the side of formality may work to start, Young says it could be a signal to coworkers that you are seeking a more hierarchical structure, which runs against the one encouraged in your new workplace.

Mary Lou Andre, a coach, speaker, and corporate image consultant, believes that this is an ideal time to properly reassess your closet. “Schedule an appointment to retire the accumulated clothes and accessories that have the potential to dismiss your relevance as a key contributor to your evolving industry and company,” says Andre. Next, she suggests upping your game by updating your look with clothes and accessories that are age-appropriate, yet communicate a sophisticated and modern approach to dress. “This doesn’t mean changing who you are and what you stand for,” Andre says. “Rather, it means paying attention to workplace trends and following suit in a way that gives you clout with a multigenerational workforce.”

Brown recommends giving thought to what is flattering for your age and body type and what makes you feel confident. “Your clothing should accentuate your feeling good about your ability to do the job,” she says, adding, “You should dress to feel polished, and to earn respect, even if you are learning a new role.”

Finally, for those who’ve spent their careers climbing to the top, Jill Martin, Today Show contributor and creative director of QVC G.I.L.I. Collection, believes the more senior you are, the more leeway you have to “play” with what you wear. “I think at a certain level you earn the right to wear what you want,” Martin says, although that doesn’t necessarily mean more dressed up. “I had a boss who wore jeans and a blazer to work while I always wore slacks,” she recalls. “The rules are not the same.”

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About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.

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