Ok folks, I need some recommendations for a new watch.

My currently daily is a slim Skagen something-or-other with a leather band. I appreciate its low profile and good looks but I think I need something a bit more up to the task.

Some info:
-Not looking to break the bank - figure I can get something in the $200-300 range as to not worry too much about it.
-I plan on wearing it the majority of the day with few exceptions (take it off to play hockey, for a road ride, sleep, shower, etc.)
-I commute via mountain bike on days where the trails are reasonably dry and on the road when it rains. Water/dirt proof is a must, I also tend to wear through leather bands with a combination of rain/sweat.
-Analog preferred but with low/no maintenance, no need for digital or smart capabilities.
-I'd prefer if it were not too heavy
-It's gotta look good and relatively modern/minimalist as in not too busy on the watch face - think Skagen, MVMT.

Thanks!