Like:

• The jacket. That olive-green has military roots and it makes a casual jacket like this  look very masculine. And yes, you can “pop” the collar of your outerwear as it’s designed to sit up against your neck to keep you warm.
• The sweater. A crew neck dresses this whole look down and gives it the right High/Low look he wants. A V-neck would still be good, but it would dress it up more.
• The bag. A more streamlined or classy weekender doesn’t fit with jeans and boots. You need a canvas or nylon duffel like this.
• The boots. One of the best things about fall and winter is the embrace of substantial footwear. I like keeping things slim on my feet during the warmer months, but you need some physical and visual weight on your feet in the winter.

Fence:

• The colors. They’re all really good for his complexion, but he needs something with a bit more contrast. The bag helps provide that, but you don’t want to carry that around all the time to get the right contrast to keep people focused on your face instead of your clothes.
• The jeans. The color is awesome and I like slimmer jeans. However, these look a bit too skinny with boots on. It helps that he has them cuffed, but if they were an inch wider in the legs they’d be perfect. That same visual weight you want in your boots in the winter also applies to your jeans and cords.

Don’t Like:

• The beard. Dainty chin straps usually look too urban or too metrosexual. Neither one of those is appropriate for the rugged vibe the rest of his outfit puts off. Most white guys can’t pull off the chin strap anyway. He would look much better if he let his cheeks grow in and still kept it all trim.

PS. Have you gotten your Style Evaluation? It’s a great way to know the strengths and weaknesses of your current wardrobe.