Throughout the late 70's, 80's and early 90's I wore black wing tip shoes to go to the office. The standard was Florsheim Regals if I was feeling particularly loaded. They were either $100 or $125 for most of that time period. The soles were leather, particularly slippery when new and on carpet, and heavy, perhaps a couple of pounds per shoe. At cash flow intervals I'd buy a cheaper pair that were about $85. Every six months or so I'd have new half-soles put on them for about $30 at the Skyway Shoe Repair.
In the mid-90's I started to get tired of lugging those brick around on my feet and purchased a pair of lightweight wing tips made by someone like Dexter (that's not right, but close). A very important VP at work (JPK) had a pair and I once asked him about them. It was a pretty personal question and perhaps a bit embarrassing for me. I thought he had a good job and was important and perhaps even thought that some people might think lightweight wing tips to make one a lesser man; maybe you could wear them, but in low light conditions of lower notice ability.
Two pair made it into my shoe stash. Of course before I knew it people quit wearing suits, going business casual. The two pair that I purchased primarily to be sneaky only went thru one resoling each before ending up in the back of the closet. Three years ago I evaluated one pair to be beyond 'work wear' and started wearing them for yard work. The red pair is 'fall red' purchased for $2.00 per gallon at Knox as miss-mixed. In 2001 my son and I replaced some siding on the 'cabin' and the paint made it onto the siding, onto my son and onto my $100 lightweight wing tips.
The laces are good but my feet seem to have grown over the past two to three years so I just let them flop. In June, July and August I just skip socks when working in the yard. My wife and the retired guy on one side of me like to alert me to my untied shoes. It just reminds me that I don't wear heavy wing tips any more, and that I'm never going to buy another suit. I haven't told my wife that but I think she knew it before me. The retired guy on the other side of me has holes in his pants; he doesn't look at my shoes and I don't look at his. We do dance around the issue of lawn chemicals and weeds, generally not criticizing each other's techniques or weeds. I don't tie the shoe laces.
The black 'cap toe' shoes just showed up from L.L. Bean via the internet. When I purchased the wing tips in the early 90's there was not any internet commerce taking place. The clerk at Rosedale probably thought there was a career in shoe selling. The wing tips are a 10 1/2 or 11. The 'cap toes' are 11 1/2 medium. My brown shoes are all purchased from the internet, too.