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"Confidence is key" and all that ... but there's so much truth to cultivating a style that works with whatever your natural strengths are. I'm not referring here to natural cosmetic / physical attributes. Let me explain.
I've got a buddy who, from the neck up, is Brad Pitt with a beard but, unfortunately, spider wrinkles and smile lines all over his face. Too much sun for too long. He's mid 40s but, unfortunately, looks noticeably older than that. But He also rocks a full sleeve of tattoos and wears flatbrim ballcaps and hoodies with associated "loud" sneakers. You'd think he's some sort of Cali skater bro ... because he fucking is. He's actually "that guy" who had to grow up and get a corporate job (M&A lawyer) but never actually left his authentic teens-20s self behind. He collects boards and knows all of the esoteric band lore of 80s and 90s punk / ska coming out of SoCal.
He has to fend off the ladies (often 15 years + his junior) like they're swarming the Beatles.
Another friend is mid 30s and bald (not by choice). He leans into it and shaves his head now, but wears a very neatly trimmed red beard. You wouldn't call it bushy at all, and it some how highlights his excellent jawline rather than hiding it. I'm not entirely show how that works. He dresses more formal than is called for for every occasion, but doesn't over do it. (We got lunch over the weekend and I rolled in to the BBQ joint wearing jeans and tee shirt, he had pressed khakis, a tucked oxford shirt, leather loafers). He likes to dress nice, it's kind of his thing. A hobby, a sincere passion. He is aloof and was probably going on 30 since he was 12. He collects and trades rare books. He'll actually read minutes from Fed meetings. The result? He gives off Professor-X Daddy Vibes and does even better than my Skater Boi.
The stereotypical heavyset dude with a homeless man beard often also apes cartoonish relevance to masculinity. "I oil my beard with the blood of dragons" Or something equally cringeworthy. He might get into long winded discussions about the history of specific weapons in LOTR or star wars. They might have an ostentatious pocket knife or .... wallet chain. The point is that they're trying to lean into something that is inauthentic and they're doing it way too hard. This isn't good. Better to reflect your genuine personality - I had another buddy who was exactly this but was just a jolly "I really like drinking beer" dude. Knew a ton about IPAs. Didn't beat you over the head with it but would talk about it appropriately if it came up in the conversation. Now, I can't say he was doing quite as well as my other two buddies (so many buddies!) but he landed a long term girlfriend that was, frankly, out of his league. And I was very happy to see that.
A lot of guys fail in developing style because they try to "dress correctly." There's no right or wrong with style independent of the person who is styling it. I think this even applies to celebrities. Johnny Depp can ransack the nearest homeless encampment and stumble down the red carpet to applause, but George Clooney has been suit 'n loafers for like 20 years now.
Similarly, there's no way to fake a personality. You can rapid fire references to memes all you want, but if you have nothing authentic to say, you're going to lose to the dude who can somehow make The Beige Book interesting. Because he thinks it's actually interesting.
Men's style is still far, far easier than women's because that's a whole other level of complexity (make up, accessories, jewelry, fucking shoes on shoes on shoes) plus the meta-game of following trends or purposefully not following trends as a meta-trend in itself. That shit is literally Martian Hieroglyphics to me.
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