This Toronto-based company makes the most adorable handmade underwear for men and women, but it's really the men's briefs that I love. With contrasting patterns and strategically placed imagery these briefs ($30) would make the perfect stocking stuffers. Vist The Candi Factory. for their online store. International shipping is available.
Sundance actually has a section on their website dedicated to manly man gifts! There's all kinds of interesting gift ideas on this site. I love the Stanley flask ($25) that has the look of the workman's favorite thermos, but is a more unusual shape and size. Holds 1 pint of your favorite beverage.
Or, for the more literary guy on your list I love the manly man book collections. For $98 you get a set of 8 books by authors like Raymond Carver, Dashiell Hammett and Joseph Conrad. Two different book collections are available all with a great selection of must-read fiction.
If you are ready to splurge a little watches are always great gifts. For the surfer I love this Freestyle watch ($150). It comes programmed with 15 years of tide information for beaches all over the world! Backlight for viewing in the dark and water resistant to 100 m. Available at Urban Outfitters.
For the less sporty look I love authentic vintage watches. There are all kinds of sites selling vintage watches out there. Prices can get pretty high for watches in pristine condition or vintage rolex's, but I actually like the look of a little wear. You can find great 1950's watches with new straps for under $300 like this Hamilton watch ($300) from Cool Vintage Watches.