Every guy at some point has probably seen and been envious of a ruggedly styled fall/winter look at some point in his life. Maybe it was the high combat boots, maybe it was the distressed denim, maybe the subtle earthy colour palette, or maybe everything all together. However, the problem for many of those men then becomes how to pull off their own take on this look while still nailing the overall tone, and how to put this look together with things they already own - or as cheaply as possible.
Right off the bat - the rugged fall look is all about texture and material. To look rugged, you have to go with pieces that were originally meant to stand up to the rugged lifestyle. Read: tough leather, thick denim, rough canvas, insulating flannel, etcetera. You probably have all the makings of the outfit at home right now, you just have to pick the right combination. Denim pants and jackets, leather or canvas high boots, a chambray shirt, a flannel or puffer vest, and a knit toque.
For this look, you've gotta think like you're actually going out to chop wood, bring your rifle out to the country shooting range, or tame a wild bear. Don't be too fussy about matching similar colours or getting certain fits, just pick your outfit based on the resilience of the material. Like Travis here, once you've got those basics down, feel free to add some personal flare like half-lacing the boots, donning a pattern-trimmed shirt, and/or rocking some clean sunglasses - unless of course you're actually going out to tame a wild bear.