The first step to staying warm without looking like an eskimo would be a respectable group of sweaters/shirts. It's difficult for guys to wear wintry clothing without the risk of looking like a grandfather, so I suggest some more modern sweaters, such as the one at left. It's warm, it's a sweater, but you don't look like Mister Rodgers. Pullovers like these give you a little bit of personality and heavier knits will help to keep you warm. This seems like a good time to advocate for layers. It doesn't really matter what you wear underneath, as long as you don't look lumpy and whatever parts stick out look clean and neat. You may want to stock up on some layering shirts that you can just stick under an outfit at random for some extra warmth, including just plain long-sleeved tees, or even a button down shirt, if you're feeling bold. Adding a scarf to any outfit is also man-friendly and seems to be a trend with staying power. Make sure, though, that you get a long scarf that will dangle to your waist, because it's really meant to be an accessory to your outfit. It just so happens that it will also keep you warm.
The legs are next on the list, and of course jeans are an excellent fallback plan, but what if you're sick of jeans? Let me take this opportunity to introduce you to a warmer, autumn-friendly cousin of denim - corduroy. The corduroy pant is wonderful because it is a heavier fabric and comes in more colors than just blue. Our model has on a pair of black cords, illustrating that while black jeans are a little odd, black cords are perfectly acceptable - even a little dressy. You don't have to put a belt on them and tuck in your shirt, though. Cords can be casual, too; just slap on a sweater and you're good to go. They also come in a variety of man-friendly, earth-toned colors that look good with almost anything in your closet and will look great all broken-in for that Saturday afternoon look.
Now that we've solved the torso and leg temperature problem, our next step is to get good cold-weather footwear. Brace yourselves - you may have to go out and buy a new pair of shoes. I know, I'm asking a lot! You had to break down and buy those oxfords, bringing your collection to a staggering two pairs, but now neither of those will suffice if you're dealing with slippery surfaces and casual occasions. A good, casual, non-work-oriented shoe is the way to go on this score. By that I mean don't go get a pair of workboots and call it a day. Do you work in construction? Are you a lumberjack? If you answered no to both of these questions, don't bother. Instead, let me recommend the handsome devils at left. They're a great color for fall, they have lug soles for slippery surfaces, but they're slip-ons, so they're casual and lazy! Really, what more could you ask for? You can find these at your local Sketchers store. Now, you have your orders, so go out and go shopping!