Vary The Fabrics
When putting together an outfit featuring a number of different layers, one of the most important things for a guy to bear in mind is to vary the texture and fabric with each new piece. The alternative is winding up with something akin to the denim shirt with jean jacket look, which is never a good thing. You don't need to go to crazy lengths to make sure each bit of clothing is an entirely different fabric, but always keep in mind it's best not to layer three or four similar pieces one on top of the other. It tends to look a little careless and feel a bit awkward.
Consider The Overall Bulk
The general strategy in layering is to start out thin (say, a basic undershirt) and work your way up to thicker and heavier pieces. But in some cases, such as with bigger guys, a simpler approach can work just fine. Flannel shirts are popular in winter collections for men, and offer a strong foundation for a layering approach that will only consist of two or three items. A heavier shirt like this with a coat can be just fine on all but the very coldest of winter days, and saves you from feeling like you're carrying around extra bulk or a cumbersome number of layers.
Include Accessories As Outerwear
It's a mistake to think of outerwear and layering as only pertaining to shirts, vests, jackets, and coats. The truth is that some of the most effective ways to dress for varying weather involve some accessories that can keep you warm, but don't add a lot of bulk or complication to your outfit. In particular, lots of dudes are wearing scarves and hats to help with seasonal layering, as they can cover parts of the body that have a lot to do with maintaining comfortable temperature (such as scalp and neck) without making you feel like you're wearing half a coat closet on your shoulders.
Embrace The Camel Coat
Lastly, I'll touch on a more specific garment trend, which is the camel coat for men. With the exception of lighter khaki pants, a camel coat can go with just about anything, including jeans, trousers, corduroys, and a range of different colored suits. That makes it a very versatile yet stylish outerwear option that can cap off pretty much any layering approach you want to try out for the remainder of this winter season.
Outside of basic tips like these, layering pretty much demands creativity. It's each individual's decision how to go about the process, but with the right approach you can put together a stylish outfit that works for multiple seasons in a day's time.