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The great closet conundrum: women, it's more than "what to wear"

Steve Jobs' signature black turtleneck, jeans, and sneakers were as much a fixture at Macworld as the gadgets he unveiled while wearing them. Still, his decidedly repetitive fashion choice was greatly overshadowed by his business acumen and the Apple product du jour.

Which begs an unnerving question, the answer to which many of us can hazard a guess: Would the appearance of a female leader, clad in the same outfit she wore last year and the year before, speaking on any topic to thousands of people at a professional conference, be as readily relegated to the fringes of the news cycle?

A woman’s armor is a weighty one

Clothing is the armor we put on to face the world. Though it's the only thing that touches us continuously for hours on end, choosing the right outfit can be a surprisingly weighty decision. Multiply that by a thousand as you stand in front of your closet, wondering what to wear to a conference full of would-be LinkedIn connections and business partners. Multiply further if you're a woman.

In describing their closet conundrums—a conference, a networking event, a job interview, or a VC pitch—women describe it like a balancing act between two extremes, on multiple axes. And the fairer sex say they are more on the precarious side of the balance beam.

In describing their closet conundrums—a conference, a networking event, a job interview, or a VC pitch—women describe it like a balancing act between two extremes, on multiple axes.

Career people, particularly women, have a hard time admitting that “getting dressed” takes up a fair bit of advance planning energy. But women are also the ones We want to be sensible and stylish. Comfortable yet elegant. We want to stand out, but in the right way—that is, in a way that doesn't make us subject to anyone's side-eyes.

As Ravneet Vohra, Editor in Chief and Founder of Wear Your Voice, puts it: "You want to look like you have your shit together.”

Short of turning the train around on long-established social constructs and gender politics, three career women offer their pro tips, while opening up about their own anxieties, in overcoming the conference closet conundrum.

Toeing the line

Nadyne Richmond is a software engineer, the lead of a UX team at Genentech. She has organized her share of conferences and spoken at several. This year, she is Co-Sessions Chair for the MacTech Conference. She describes the pre-packing scene, and it's familiar to a lot of us who've been there: standing in front of her closet, feeling mocked by a still-empty suitcase and the ticking countdown to boarding time.

"I start with shoes because shoes are what will kill you," Richmond cautions.

Conference centers aren't great for walking. Their floors are often unforgiving concrete or some freshly buffed slip-hazard. Unless you find a niche among the cadre of folks gathered on the office carpet (or seated near the all-important charging stations), you'll find more people standing and walking versus sitting. Given these realities, Richmond's metric: What shoes can she easily do 15K steps on, per her FitBit measurement? Her go-to—easily clocking in at 30K steps—is a pair of black booties, equally at home with skirts or pants, with a two-inch heel.

Working her way up, she typically sticks with basic black, choosing pieces that can easily be dressed up or dressed down to achieve a balance of formal and casual. Dark jeans, a nice top, and a blazer are always a hit. Slacks are great—but not with the nice top and the blazer because it disturbs the casual-formal axis.

Vohra echoes this confidence-inducing comfort: "Comfort, comfort, comfort, all the way. Less is always more. If you're not comfortable in heels, don't wear them."

"Comfort, comfort, comfort, all the way. Less is always more. If you're not comfortable in heels, don't wear them." - Ravneet Vohra

Color yourself confident

Aleatha Parker-Wood, a computer scientist and researcher with Symantec, is a regular at the RSA Conference, which focuses on information security. She agrees that comfortable shoes are key, whether you're presenting or attending, saying her two-inch Frye's pumps, with lightly padded leather, usually fit the bill. And don't be afraid of color and contrast; she most recently wore a bright white shirt and a blue blazer that cleared the bars of fashionable, confident, and capable.

Though she self-places more on the butch end of the traditional masculine-feminine spectrum, she notes that "to skirt or not to skirt" is among the first roadblocks women run into.

Still, it seems like the skirt stays on the hanger when push comes to shove. The reason being simply that it's harder to dress a skirt down in a way that still feels professional and fashion-forward.

Parker-Wood, like Vohra, aims for the happy middle between formal and informal. Pack your jeans and a nice jacket, she says, as well as slacks and a nice top. But you may find yourself a little off if you mix the jacket and the slacks.

Accessorize with your eyes on the prize

Vohra, in her role at Wear Your Voice, is the one pounding the streets and knocking on investors' doors as the face of the venture.

"You have to see our color, our presentation, our gender, our sexuality, our experience, our anger, our happiness—you won't see any of that if you only hear our voices," Vohra says.

Given the highly visual nature of her business, and as someone who previously worked in the fashion industry, the microscope is often especially trained on Vohra, whether people realize it or not. Even when she worked from home, she'd put on makeup and, yes, even perfume—it's part of her armor and it makes her feel good, she says.

"It's not like I pop into my wardrobe and have a make-it-work moment," she says, acknowledging the forethought.

The conference conundrum solved

  • If you're not comfortable in heels, don't wear them: dress up your outfit in another way.
  • Stay within your comfort spectrum—feminine/masculine, formal/informal, flirtatious/somber. Your conference wear should always draw from these sweet spots,
  • You can't go wrong with basic black.
  • If you go dressy with pants, dress it down on top. And vice-versa.
  • Pops of color help you stand out in a good way.
  • Ditto with statement jewelry, which can also serve as a memorable conversation piece.
  • Get comfortable and stay comfortable. Wear what reflects and represents you.

Vohra's conference go-to: "A really smart pair of jeans, and a blazer that makes me feel confident. I have my power suit on, and I'm ready to go." Combine that with her easiest, but arguably boldest trick of the trade for dressing up her preferred sea of black—amazing accent pieces. Think a fancy ring, a chunky necklace, or a brilliant scarf with a lot of psychedelic colors in it.

Bonus: These items also become talking points, the most inoffensive icebreakers whether you're presenting on a panel or having a conversation in the hallway. For Vohra, being forgettable at such events is the kiss of death.

"I've not gone all the way to Washington, D.C. to be forgotten about," she says. "I want people to remember what I do and where we're heading and what we want to achieve."

Dressed up, but dressed down. Accessorize to win. Comfort all the way, especially with shoes. Easy, right? Not quite. It's clear that there is an anxiety, but what is its root?

"It's judgment, and it's wanting to fit in," Richmond summarizes. "You want to be yourself, but you want to be yourself within a standard deviation of one or two of everyone else."

"You want to be yourself, but you want to be yourself within a standard deviation of one or two of everyone else." - Nadyne Richmond

Business casual is anything but

One of Richmond's pet peeves is the term She recalls a conversation with a friend, a male hiring manager, who often sends emails about interview dress codes and business casual attire. He thought he was helping, she instead told him, "If you say that to a woman, you haven't told her anything actionable."

"He argued, 'No, it really means something,'" Richmond recalled. "He went on about khakis and a polo shirt, but [women] don't have that equivalent. And he admitted he'd judge a candidate negatively if he didn't like the outfit."

He's not the only one. Research backs up the claim that women are judged more harshly on appearance, particularly when it comes to job interviews. Women are typically more spoiled for fashion choice, and it's not necessarily a good thing. For example, you could go with a pencil skirt and a sweater. But how deep is the neck plunge on that sweater, and how tight or short is the pencil skirt? Are you properly toeing the subjective line between too conservative and too showy? And are you being noticed in the right way—or not at all? Because if you aim too close to average, you'll blend in too much. Take it from Parker-Wood, who was (yikes) mistaken once for one of the uniformed event staff when she was actually a featured speaker.

What about the men?

Not that men don't have anxiety about what to wear, or have similar concerns about putting their best foot forward. Parker-Wood, though, notes that it simply plays out differently given the additional variables at play.

"Guys have asked me what they should wear, whether they should dress a little up or down," Parker-Wood says. "But for women, there is this extra layer of signaling on top of it."

With women, there's the formal to informal spectrum, the hyperfeminine to hypermasculine spectrum, and what Parker-Wood calls the "flirtatious to somber" spectrum. Where do you normally sit on all of those? Most men, by contrast, typically sit on a spectrum between formal to informal. Vohra posits that most men could throw on a funky-heeled shoe and a leather jacket and look incredibly thought out and put together. Women, Vohra argues, simply can't pull that off.

Vohra also has some frank words for men presenting in t-shirts, jeans, and sneakers: "When you're putting yourself on a stage, you should make sure you are honorable of that stage. Not everybody gets the stage and the whole audience to clap and applaud—the least you can do is put on a nice outfit and present, represent, or inspire; but to arrive in your home wear is offensive. I find it very, very offensive."