When I wear cufflinks I often imagine that my man Q has outfitted them with deadly lasers, two-way radios, and poison pills. Cufflinks were after all, the perfect compliment to the Cold War spy.
Baseball cards, red wine, and blue jeans all get better with time (provided you find the right pair of jeans).
When I wear my favorite gun barrel grey wool suit on the streets of NYC it turns heads. You get that wry invitational smile from women who are dressed up too. They appreciate the gesture, gentlemen. Wool suits bear a certain cachet and reflect a maturity and control. Presidents seem to sleep in them.
Messenger bags. To the urban man, they are a must. You need something for which to lug your stuff: the laptop, mags, papers (rolling or otherwise). You want something functional but not unsightly. As a man who drags his belongings around NYC daily and feels quite naked without it, I know from messenger bags.
Try a blue and white oxford or a chambray chemise under a dark mahogany leather blazer for a classy look that works any time of the year.