Drive de Cartier
For the gentleman who wears a suit on a daily basis, the flat body of the Drive de Cartier is perfect for under those thick winter layers.
The TUDOR Pelagos is great for active types due to it being made of lightweight titanium. It has a self-adjusting clasp which means the bracelet fits comfortably whichever activity is undertaken.
IWC Schaffhausen Portofino Hand-Wound Eight Days
For a weekend away, my suggestion would be the very classic IWC Portofino Hand-Wound Eight Days. Its deep brown leather strap and red gold case make it the perfect watch for winter outings.