I know how to buy a pair of running shoes. I am out of my element when it comes to other sports shoes and even more out of my element when it comes to dress shoes.
I currently own 4 pairs of brown shoes (cowboy boots, bicycle toe oxfords by Sketchers, apron toe loafers, and plain toe oxfords by Johnson & Murphy). I also own 3 pairs of black shoes (plain toe oxfords by Sketchers, apron toe oxfords by Rockport and cap toe oxfords by Nunn Bush). Of the assortment, I may wear all of them less than 10 times per year. However, all of my shoes feel tight. I had some foot issues in the past and am starting to appreciate more wiggle room for my toes, especially when I was wearing custom orthotics. I accidentally purchased running shoes in a 9.5 versus my usual 8.5 a year ago and my feet have felt great in them.
Now as occasion comes up, I am in the market for new shoes. In terms of style, I prefer oxfords and will be unlikely to purchase loafers in the future. I also prefer simple shoes and will rarely reach for wingtips or shoes with significant broguing.
The first stop was new shoes to wear with my suit. I limited my choices to cap toe oxfords and was unpleasantly surprised by pressure at the top of my foot with the Johnson & Murphy and Rockport lines. The Ecco Helsinki felt great, but had a slightly squared toe and lower gloss finish. This makes the shoe more functional for me in terms of wear with casual pants or even jeans, but slightly detracts from the effectiveness as a true dress shoe. The only alternative for me was the Allen Edmonds Park Avenue. This shoe felt great and has tremendous styling. The only detractor was cost. It is a less versatile shoe and also has a leather sole versus polyurethane sole. I did not try the Kenneth Cole brand as I was warned they would take longer to break in.
The Allen Edmonds line was pitched as an investment. In fact I would be willing to replace the soul and even have the shoe reconditioned. I also think they are worth the money in terms of construction and styling. I was even taken in by the velvet shoe bags and stories about US President who wore them for inaugurations. However, I do not wear dress shoes for work and am purchasing a shoe for rare use. Comfort and fit most important and I am willing to sacrifice style and back story.