I am not really a "military person". I hang out with a lot of pacifists, hippies, poets and artists- so the military is not really my scene. But vintage military pieces can always be in style. Here are a few that I recommend:
+ The Military Coat
I really enjoy a good military coat. Perhaps it is the buttons, which play upon my penchant for 1960's mod. I have a black sea captain's jacket and a grey wool trench they are two of my favorite pieces. I build my outfits around particular items- vintage military coats are a great place to start.
+ The Haircut
Every man within forty miles of a barber is currently trying for some version of this haircut. It is part-classic, part-rebel. which, in my opinion is the perfect combiniation for a gentleman. To err on the classy side- leave it longer on the crown as Xavier Dolan does in the second image.
+ The Book
"The Seven Pillars of Wisdom is perhaps one of my favorite books. Second, perhaps to "With Lawrence in Arabia" by Lowell Thomas- which is really just a book about this book. What makes a military book a good book in general is when it tells a story of adventure that has more to do with history and humanity than waging war on your nation's enemies.
Military backpack? I'd wear that! This one is updated with a great color. You really cannot go wrong with military gear- in canvas or leather. If you are using vintage, make sure that you remove labels and patches before traveling abroad.
+ The Transportation
I really like the idea of this shiny black Vespa. tres classy... yet it has a military vibe. One would look a bit too "third-Reich" rolling around town with a side car. This is much classier.
+ The Boots
Perhaps they still have a "punk" connotation- but I think that combat boots can be done in an updated way. They are very utilitarian- boots that are durable but can shine-up to look great with a suit. My friend Kirstin Stiebel believes strongly in combat boots. She would be so proud.
(Photo Source: Coat. Hair. Xavier. Pack. Vespa. Book. Boots)