Take for example this navy pinstripe Brooks Brothers sack paired with a knitted tie:
Navy pinstripes= business formal. Knit ties= dress casual. Do I care? Not a bit. As I've said before, a willful disregard for the rules can mean the difference between style and blind conformity.
So too these grey socks and brown shoes with navy pinstripes:So wrong it's right. A man is "supposed" to wear black shoes and navy socks with a navy suit. The hell with that. The grey socks pick up the grey knit tie, further making it "work".
As for the small details, a man's jewelry should be discreet. It certainly shouldn't be a safety pin:Yes, a real safety pin, not a tie tack made to look like one. Straight out of the sewing box, through the tie and into the placket of the shirt. Call it a nod to my youthful escapades in punk rock, call it sprezzatura, call it whatever you want. Why would I do such a thing? Because I can.
Guys are always complaining that suits are restrictive and uncomfortable, and many people believe the suit to be the ultimate symbol of an oppressive establishment. That's only true if you believe it. Wearing a suit, especially if you don't have to, can allow a man to set his personality free. Sure, you can set yourself apart from the crowd with funny haircuts and tattoos...I've done that before. But in a world full of grown-ups walking the streets in children's clothes and pyjamas, out-dressing every guy in the room gets 'em every time.
p.s. I stole the safety pin idea from an Italian guy named Beppe. The man's a real bad- a*s.