I think the three pieces of clothing (or accessories) that stand out the most are shoes, a belt and a watch and I guess out of those three shoes stand out the most. I stopped wearing square-nosed or long dress shoes some time ago and prefer to wear something more classy and bold, if I may say so.
It also makes sense to invest into a couple of pairs of good shoes that can last you for many many years if you take care of them and don’t wear the same pair every day. I really like American made Allen Edmonds shoes. They are high quality shoes that can be had for not an obscene amount of money. They are made of high quality leather and they are sewn to their leather soles, not glued, as proper shoes should be. After a couple of days of wearing the leather molds to your foot and they become very comfortable.
They come in many different styles and colors. Three of my favorites choices at the moment are McAllister Wingtip in walnut — works as cusual as well as a dress shoe, Fifth Avenue Cap-toe in black — goes with pretty my anything and for anything and McTavish Wingtip in gray — simple casual shoe. Allen Edmonds typically has pretty good sales later in the year and that’s when I plan to add Strand Cap-toe in brown — a pair of very class dress shoes.