Why I Think First-Date Outfits Are Overrated

Google "first-date outfit" and you'll find over 4 million results weighing in on the subject, from expert opinions on what to wear to style mistakes to avoid at all costs. While the intentions are nice—help us score romantic points, sartorially—the reality is that these strict guidelines negate our individual personalities, sweeping our style quirks under the rug as if to say, Who you really are won't do—try this on for size instead.

Not to mention the fact that never in the history of the world has a healthy, long-lasting relationship been formed by people hiding their true colors in lieu of something more palatable and, perhaps, mainstream (correct me if I'm wrong). So, while it may seem innocent enough, caving to outside opinions on the dos and don'ts of first-date wear that don't necessarily align with your style is really just an effort in convincing your partner to fall for someone you're not. What's more, it's an act of self-flagellation, a way of reinforcing that your inclination toward wide-leg culottes or jeans and a vintage tee renders you somehow less than dateable.

Opt for a little black dress; pair jeans with heels; show some skin; don't wear anything too trendy—the list goes on.

I wholeheartedly reject these rules, as they feel both anti-feminist and anti-fun, quashing personal style quirks and the freedom that comes with fashion for the seemingly noble cause of romance. To that, I say nah—real connection transcends such frivolities, but can also only happen between two authentic parties (wearing what they like when they like).

Having occasionally caved to these rules myself, I also know the discomfort they bring, contributing to nerves and that audition-like feeling that first dates so often hold. Like me for who I'm only pretending to be, these looks seem to shout, followed by an inner monologue of Ohmigod why did I wear this? I'm so uncomfortable. Instead of paying attention to the person in front of me, I find myself expending way too much energy on the components of my outfit, wishing I could run back home and change into something more "me."

When I forgo the rulebook, though, I feel my confidence rise—it's that self-assuredness via style that drew me to fashion in the first place. Proudly wearing what I like to wear, even if it's considered too casual or unsexy for a first date, reminds me to be proud of who I am and to look for someone who likes that person, not say, a sparklier, magazine-worthier version.

Scroll down to shop some of my quirky and comfortable first-date outfit picks…

Vows: A Healing Couple, Leading With Their Hearts

Despite her success, she is without pretense, Dr. Clapp said: "She is the same person everywhere she goes."

Dr. Keith's father was a Tuskegee Airman (World War II ended before he could actually enter the fight) who went on to Harvard Medical School and did his pediatric residency at Boston Children's Hospital before moving his family to Chicago.

Dr. Gayle had met Dr. Keith in 1979, at the Student National Medical Association Conference in Los Angeles. She was a medical student at the University of Pennsylva nia, and he was a resident at U.C.L.A.

Dr. Gayle, now 60, recalled thinking of him then as a "kind, slightly older guy." "He was in his residency and treated little old me in a very kind way," she said. "So he stood out."

Dr. Keith, who at 63 resembles an older version of the former professional tennis player James Blake, recalled her then as bright, eager and attractive.

Both doctors received degrees in pediatrics and public health. Dr. Keith soon had two daughters from his first marriage.

By the late 1980s, Dr. Keith had begun to see more of Dr. Gayle in his role as an aide to Senator Kennedy, working toward passage of the Ryan White act, which improved care for patients with H.I.V./AIDS. But even when Dr. Keith found himself single again in 1987, no romance ensued between the two.

"We actually would see each other here in D.C.," he said. "She was at the Centers for Disease Control, and I would have to go down to Atlanta. And then in the early 1990s, she headed up the D.C. office for the C.D.C., and we intersected. But it was collegial. I just didn't see it."

He remarried in the early 1990s, and had a son.

Their mutual passion for addressing H.I.V./AIDS and what Dr. Gayle calls the social justice imperative of helping marginalized populations deepened their friendship. Dr. Keith's professional purpose was undergirded by a personal one: His sister, Julie Keith Jarrett, died in 1994 of AIDS, and she left behind a husband and a daughter.

About five years ago, his second marriage began to unravel.

By the fall of 2011, he was working as chief executive of the American College of Clinical Pharmacology, and she was the chief executive of CARE in Atlanta. The gap between their dinners had stretched longer than in the past, and their conspicuous absence had made him wonder if it was something more than just conversation that he was missing, if a missed opportunity might not yet be a lost one. So he made that life-changing call to Dr. Gayle.

"I had always known she was a wonderful person, beautiful, caring for other people," he said. "I said she has been here this whole time. And I just didn't see it, and I will try to make up for lost time. I will try to do it right."

Dr. Gayle recalled the phone conversation: "He said, 'We haven't talked for a while.' I kind of had a suspicion, that it was potentially about us."

In town for her nephew's wedding, she agreed to meet up at Jackie's Restaurant in Silver Spring, Md.

Dr. Keith tried to play it cool. "I did not say to her, 'This is the start of something serious' on the first date," he said. "I really enjoyed the time, but in my mind I knew this was it. I knew I didn't want to focus anywhere else."

For Dr. Gayle's part, too, something sparked during that dinner that was 30 years in the making. "I looked at him differently," she said. "I remembered how handsome I thought he was. I remembered how much fun we had in each other's company, and it just unshackles someone from a particular box and you start seeing them in a different way."

She had also recently ended a long relationship, and was winding down her role at CARE. (She is now C.E.O. of the McKinsey Social Initiative.)

"I think my head made room for my heart to take over," Dr. Gayle said, thinking back to the early days of their courtship. "I remember being at a dinne r with friends, not long after we started dating, and he was just staring at me as I talked with this warm, loving look in his eyes. I was blown away. I am not sure I had ever had anyone look at me like that."

Dr. Reed Tuckson, a longtime friend of both, said he was struck by how deeply Dr. Keith had fallen for her, noting that he usually kept his emotions well hidden. "You'd have to sort of push Steve," Dr. Tuckson said. "If Steve tells you his arm is sore, you have to see if he has an arm. It was a real surprise when he started talking about Helene. I said, 'You are talking about our sister, man!'"

Things began to move quickly. In February 2012, Dr. Keith moved in with Dr. Gayle in Atlanta, and took a job with a medical firm there. (He is now chief executive with Vivacelle Bio, a biotech company.)

That summer, he joined her in Chautauqua, N.Y., where Dr. Gayle's enormous extended family has assembled for generations. Alana Gayle, Helene's older sister, said that her granddaughter had immediately proclaimed Dr. Keith her favorite uncle, a good sign of permanence.

"It was like he had always been here," Alana Gayle said.

There Dr. Keith saw Dr. Gayle as her family does: as Aunt Helene, just happy to cook and pick up the rental bikes. He loved that she was as comfortable in that space as she was sparring with world leaders over public health crises.

The question of marria ge, though, was one that Dr. Gayle had to work out for herself. "It's easy to be intellectual about this," she said. "Is it an equal institution for women as it is for men? Is it going to change my life and my life options? Does it indicate I need someone to complete me as a human being?"

Even after letting emotion rule the day, she was able to supply a fairly thoughtful rationale for matrimony. "There is something about the act that a public commitment does make a bond that is different and special and creates a level of intimacy that — not that you necessarily need marriage for it — but probably is facilitated by marriage," she said.

In June 2015, Dr. Keith proposed. She was speechless at first. They kissed. Then he asked, "Does that mean yes?" Dr. Gayle said it did.

On June 4, the couple were married at Christ United Methodist Church in Washington. Dr. Tuckson served as best man; Dr. Clapp was maid of honor.

Standing on the dais, Dr. Keith said to Dr. Gayle: "Falling in love with you was easy and exciting, comforting and powerful. Having waited much too long for this day, I am proud to now become your husband and for you to become my wife."

In her vows, she quoted from the book "Americanah" by Chimamanda Ngozi Adichie: "He made her feel like herself. With him, she was at ease: her skin felt as though it was her right size."

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