Reddit mentions of How To Be a Man: A Guide To Style and Behavior For The Modern Gentleman

How To Be a Man: A Guide To Style and Behavior For The Modern Gentleman by the late Glenn O’Brien is also good. He was the former style guy for GQ, and was just an all around great dude. For instance, the coolest piece of clothing he owned was a motorcycle jacket that Basquiat drew on the back of.

Dear Yarcofin,

Whilst I admire your desire to demonstrate yourself as a gentleman, despite the fact that no plebeians, such as yourself, shall ever be true gentlemen--as plebeian blood is many shades from blue--I shall endeavor to guide thee nearest, by way of the written word, to the state of the cavalier.

I shall hope you will find much erudition, form, and poise betwixt pages and pages of the following ledgers:

How to Be a Gentleman

The Affected Provincial's Companion

How to Be a Man

Gentleman: A Timeless Guide to Fashion

Dressing the Man

The Art of Manliness

Regards,

Curtains

Ines de la Fressange wrote a book about men’s style tips called The Parisian Field Guide to Men's Style, however I didn’t really like it that much because it mainly focused on menswear and seemed incredibly limiting outside of that. It basically made it seem like style rules can’t be broken in a sense.

There’s also Massimo Osti’s, the creator of Stone Island and pioneer of modern day technical clothing, book Ideas From Massimo Osti, which I think focuses on his legacy and where Stone Island is now.

Edit: And of course you can’t forget the legendary Anthology of a Decade by Hedi Slimane.

Edit 2: I'm also forgetting the famous How To Be a Man by the late GQ legend Glenn O'Brien, as well as Men and Manners and Men and Style by David Coggins.

What a shame. As a kid, I was an avid fan of his public access cable show TV Party where I learned about artists like Walter Stedding, Tuxedomoon, Klaus Nomi, and Basquiat, and had a chance to see musicians like Mick Jones, Chris Stein, and Debbie Harry, whose music I was already into, in a whole new context. The shows are on YouTube and were, at the time, subversive yet endearingly ramshackle and amateur. I continued to enjoy his writing on manners and style, and would seek out his Style Guy columns in GQ, which to me were less about matching your socks with your shirt, and more about individuality and being your own person.

If you are a fan of his, it's worth tracking down his Tea at the Beatrice interview series on Made 2 Measure. Many of the subjects were friends of his, and that comes through in each episode's loose, informal structure. I especially enjoyed his interviews with Chris Blackwell and Nan Goldin, though while watching the latter I remarked to my spouse that Glenn seemed quite ill.

How about a book on how to dress well and just be a man in general? Glenn O'Brien over at GQ penned an excellent book called How to be a Man. It is a great primer on how to dress and act like a mature gentleman. Now, it does have chapters on smoking and drinking etiquette... And Christmas seems to be more of a time for "fun" gifts that engenders happiness and joy rather than "meaningful" ones that always come with a lecture/speech/story (reserved for important birthdays or occasions). So it's your call, dad. My favorite Christmas gift from my parents has always been video games because I love that shit.

Boy it's hard to be a dad nowadays. I salute you good sir.

EDIT: I see that people are suggesting pocket knives. To be honest, the pocket knife I got from my father on my 16th birthday was arguably one of the best gifts I have ever gotten. And I think a pocket knife makes for the greatest gift for boys of any type, not just the outdoorsy ones. Because every man should carry a pocket knife with him. But again it falls under the "meaningful" category for me. It's a rite of passage, really. It's a great opportunity to teach a boy something about maturity/responsibility and power, respect and appreciation for risk and danger, etc. that kind of thing.

Read "How to be a Man" by Glenn O'Brien. Not only will it help in a basic understanding of bodily care, but also how to dress and how to act in certain situations. I wasn't taught these things either, but managed to learn on my own eventually. Acting nice > Looking nice, but both are important.

http://www.amazon.com/How-Be-Man-Behavior-Gentleman/dp/0847835472/ref=sr_1_1?ie=UTF8&qid=1321023038&sr=8-1