A man's choice of clothing for a first date can carry significant, often unconscious, messages about his intentions and state of mind. Experts suggest that while the specific items may vary, the underlying sentiment conveyed by an outfit can significantly impact a date's success.
Jabari Taylor-Reid, an entrepreneur and writer, described a "high-low illusion" approach: a premium blazer over a white T-shirt with dark denim and sneakers. This, he found, signaled respect for the date while appearing effortlessly stylish. However, an untested, stiff leather jacket led to overheating and noticeable squeaking, a mishap that ultimately ended the potential for a second date.
"My learned lesson was to never wear untested armor to a first date," Taylor-Reid stated.
Dmitrii Malashkin experienced a different outcome when he wore suit trousers and a white shirt straight from work to a rooftop bar. His date's observation that he "just come from the office?" suggested that his attire reminded her of a professional setting rather than a relaxed social encounter.
Some men intentionally dress down to mask their financial status, according to fashion designer Marcia Sherrill. However, this can be misinterpreted. "Her horror when he shows up in a T-shirt. This is signaling that he took no interest in the date," Sherrill noted, advocating for a "jacket or forget it" rule.
Brian Mahoney discovered that his favorite charcoal gray wool turtleneck, which he believed was sophisticated, was perceived negatively. "Before we even said hello, from across the room, the woman looked crestfallen," he recalled. Upon ceasing to wear the sweater, his dating experiences improved.
Sheldon Cohen, a marriage and family therapist, explained that overdressing can be "anxiety manifested in an outfit," an attempt to control the impression rather than fully engage in the moment. Conversely, dressing down can be a protective measure to mitigate the potential sting of rejection.
"Overdressing is anxiety manifested in an outfit," Cohen said. "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." He added, "Dressing down is also an attempt at control, but this time it is presented more as a relaxed approach. 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."
Amy Grammer, a designer and owner of Milliners Row, advises dressing "one notch more intentional than your everyday self," cautioning against excessive changes that can appear disingenuous.
Matchmaker and dating coach Sara Moses recounted a situation where a man wearing a tuxedo one night, and then shorts, a baseball cap, and flip-flops the next, sent a message of diminished importance. "The message I received, whether he intended it or not, was, ‘This evening isn’t important enough to make an effort.’"
Therapist Adria Hagg suggests that the intention behind the outfit—whether to impress, fit in, project status, or avoid judgment—is more critical than the attire itself. "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," Hagg said.
The perceived "luck" associated with certain items, like Simon's dark green shirt, may stem from the wearer's increased confidence and relaxed demeanor. "He believed it was, so he walked in easier, smiled more and paid attention instead of worrying about himself," the article noted, suggesting that the true "luck" was the self-assurance the belief inspired.