My friend Simon had a lucky shirt. Dark green, long sleeves, nothing special. He wore it on a first date and it went well, so he wore it on the next one, too. Simon had a run of good first dates and attributed it all to the shirt.Another friend, David, asked to borrow it, curious whether the luck was real or just Simon. He wore it on his own date and it worked. Soon, we all wanted a turn.It’s a pattern you hear quickly once you ask men about first dates. Everyone has a version of an outfit that “worked,” or something they stopped wearing because it didn’t.F.J. Jimenez via Getty ImagesFor some, flip-flops aren't ... the best option.Jabari Taylor-Reid, an entrepreneur and writer, has a formula, and it worked. Until it didn’t. “My absolute rule for a first date is what I call the high-low illusion,” said Taylor-Reid. “I wear a premium, tailored blazer or a fancy jacket over a white T-shirt, paired with slim-fit dark denim and leather sneakers. The blazer shows I respect her time and have my life together, while the T-shirt and sneakers scream that I did not try hard at all and just happen to look this good.”At a wine bar, it worked. “She loved that I did not overdress but still looked like an adult,” he said, “because the casual fabric kept me approachable while the tailoring kept me sharp.”Despite the success, the next time he had a first date, he swapped the blazer for a stiff new leather jacket he had never worn. “Within 10 minutes, my body heat turned the stiff leather into a personal sauna and I began sweating like crazy,” he said. “Because the jacket was so stiff, it squeaked loudly every single time I reached for my drink.” Off, and his shirt was drenched. On, and he squeaked. “She legit asked if I was OK.” There was no second date. “I learned my lesson to never wear untested armor to a first date.”“Overdressing is anxiety manifested in an outfit.Dmitrii Malashkin had no system at all. He went straight from work to a rooftop bar in Boston wearing suit trousers and a white shirt. His date kept glancing at his sleeve “as if she could somehow see the Excel spreadsheets I was hiding up there,” then asked, “Just come from the office?” He had not. “The only reason she should notice your shirt is that it’s interesting and not because it reminded her of HR,” he said.Some men dress down on purpose. Fashion designer Marcia Sherrill, who counsels wealthy clients on how they dress, often sees them opt to hide their money on dates. “They want to opt for T-shirts or athleisure outfits to downplay their wealth,” she said. “Imagine her horror when he shows up in a T-shirt. This is signaling that he took no interest in the date.” Her rule for all of them: “Jacket or forget it.”Not all signals are intentional. Brian Mahoney had a favorite first-date sweater. It turned out everyone else hated it. “Before we even said hello, from across the room, the woman looked crestfallen. Just bummed out,” he said. “We were still able to have decent conversations. So the dates weren’t terrible or anything.” He eventually realized the culprit was a charcoal gray wool turtleneck he loved. “Expensive. Not too light, not too heavy. Good bit of texture to it. I thought it was great.” When Mahoney stopped wearing it, “It seemed to take care of the problem,” he said.“Overdressing is anxiety manifested in an outfit,” said Sheldon Cohen, a marriage and family therapist. “When a man shows up to a date in a blazer and the date did not call for it, he is trying to control the variable he thinks he can, which is the impression. Effort is appreciated, but if someone is trying to manage the impression of a date more than he is actually there, then it is being perceived as a ‘trying too hard’ outfit.”Cohen sees dressing down as the same instinct in reverse. “Dressing down is also an attempt at control, but this time it is presented more as a relaxed approach,” said Cohen. “It protects him from the self-exposure that comes with actually ‘being there’ if the date doesn’t go well. For a lot of men, it is comfortable, protective, and tries to set a low-stakes bar so that rejection ‘doesn’t hit’ too hard.”“My rule for men: dress one notch more intentional than your everyday self,” said Amy Grammer, a designer and owner of Milliners Row. “NOT three notches.” She says the overdresser can end up looking like he is pretending to be an adult rather than fully being in the moment. Her fix is a familiar outfit with one upgrade, “a new jacket, a sharper shoe, or a shirt that is of a more lively color.”120b_rock via Getty ImagesMaybe ditch the tux and cummerbund for something a little more casual on an informal first date.At a black-tie wedding, Sara Moses met a man in “a beautifully tailored tuxedo.” Moses, a matchmaker and dating and relationship coach, held hands with him through the evening, and he kissed her goodnight. The next night, he took her to a restaurant she picked. “He walked in wearing shorts, a baseball cap ... and flip-flops,” she said. “The night before, he looked like James Bond. Twenty-four hours later, he looked like he was headed to buy potting soil at Home Depot.” The flip-flops finished it. “The message I received, whether he intended it or not, was, ‘This evening isn’t important enough to make an effort.’” There was no second date. “It’s amazing what a pair of flip-flops can do to a love story.”“What’s most interesting is that many of these choices happen outside of conscious awareness,” said Adria Hagg, a therapist. “People tend to dress in ways that help them feel emotionally safe.” The outfit, she said, matters less than the intention behind it, whether a man dresses to impress, fit in, project status, or avoid judgment. “The healthiest daters tend to choose clothing that feels like an elevated version of who they already are rather than a costume designed to win approval.”Which is what Simon’s shirt was really doing. It was never lucky. He believed it was, so he walked in easier, smiled more and paid attention instead of worrying about himself. When David borrowed the shirt, he borrowed the belief that came with it. Maybe that was the lucky part.