Sweaters
The hoodie is the security blanket of the modern preswag male. Dudes h8 giving them up. To ensure a relatively painless transition, you need to hook up him with a solid, heavyweight sweater that can take the place of his favorite sweatshirt. Avoid stuff that's too thin and dainty like Merino wool — that's way too European for your dude. Instead, get him one of those fluffy "Shaggy Dog" sweaters that preps have been wearing since forever. J.Press are the OGs of the style, but if the price is too steep for your dude, Polo Rugby and J.Crew both make similar models in a wide range of manly colors, as well as some more "experimental" tones. 

And if that is too much for him, just have him swap his hoodie for a nice, collegiate-inspired, gray, crewneck sweatshirt. He can cop one at the mall, throw an oxford shirt underneath it, and instantly look 100x better than any of the scrubs at the food court. 

J. Press Brushed Shetland Sweater, $195, available at J. Press; J.Crew Factory Fleece Sweatshirt, $24.50, available at J.Crew.