Watches are one of my passions. I have a couple dozen, ranging from about $10 to $800 ( I once ordered a $12 Chinese mechanical watch mostly out of fascination that such a product could even be *shipped* from China for that amount, much less produced).
The old forum used to talk about things like pocket squares. I rarely find occasion to wear those, but a wristwatch is a great way for a man to show off his style. In fact, they are probably the closest thing men have to jewelry.
No slight against Rolex, but you can have one nice Rolex, or you can have tons of different watches for different moods and occasions.
The cool thing is, whatever you are interested in, you can buy a watch with that theme. I have: a Polish watch, Russian watches, Chinese watches, Japanese watches, American watches (Timex Indiglo is actually pretty awesome for the price), Swiss watches, dive watches, a chronograph watch, a moonphase watch, dual time zones, a GMT, rotating bezel watches, an incredible Huawei smartwatch that blows Apple and Android away, and a tachymeter.
My advice to newbies is to start with the main brands. There are some no name or "micro-brand" watches that are a cool niche, but there are also a lot that are junk. A low end Seiko is better than a lot of no name watches costing twice as much. And while Fossil is ok, stay away from most "fashion" watch brands. They just slap a "Calvin Klein" logo on a generic watch pumped out by some unrelated factory.
Some of my favorite brands:
Orient - Japanese brand, and by far the most affordable brand that makes the entire watch in house (the majority of mechanical watches use Swiss (Swatch) or Japanese (Seiko) movements).
I like how they don't just sell watches, but also educate the buyer. I got a lot of info out of their blog when I first got in to watches:
Seiko - one of the most well known watch firms, highly innovative, has a huge range of styles and great bang for buck
While their English brand names are kinda dumb, there are some beautiful watches from Hong Kong's Sugess/Seagull, like this 1963 series which I own:
I highly recommend the Heads Up thread here that discusses sales and discounts:
The owner of Long Island Watch really loves watches, and his youtube videos are fun (they are a good shop too)
While I love mechanical watches, what watch am I wearing most of the time?
The Casio W-S210-H. I got it for <$30 and it is solar powered, dual time zone, waterproof, with light, calendar, stopwatch, timer, multiple alarms, tides, moonphase, and waterproof! Never have to set it, just grab and go, plus it's so cheap I don't worry about damaging or losing it.
Finally, this was the video that started my fascination with mechanical watches. Produced by the American Hamilton Watch company of Pennsylvania (later sold to the Swiss--I don't think there are any true American mechanical watches anymore):
This was from a time when marketing meant a lot more than paying some instagram thot to pretend to use your product.