There are so many elegant alternatives to wearing sneakers or the ubiquitous boat shoe at the weekend or with your less formal “country clothing,” that I find it hard to imagine why anyone would choose to look so “down at the heel.”
There are those, like my friend the architect, who swear by the loafer or moccasin. I spent high school wearing a pair of cordovan penny loafers and such was their construction that I only had two pair in four years of daily wear. Alden makes the quintessential cordovan penny loafer (and a beautiful suede, too), Gucci, the horsebit loafer (as worn by Douglas Fairbanks, Jr.) and Belgian Slippers are unmatched for comfort, if not being among the sturdiest choices.
But I long to cover my size 9’s with a pair of Crockett and Jones’ Unlined Suede Chukkas (seen above from Ben Silver.) Elegant because of an elongated last and actual leather sole; casual by nature and easy to pair with all manner of sportcoat, denim jeans, blazers and tweed suits, the suede Chukka is the preferred shoe of Italian cognescenti.
Chukkas are named for the “inning” at a polo match and were originally worn by polo players although they came into fashion during the 1950’s. They are really sort of a high shoe more than a boot and usually have one or two eyelets for laces.
One need not be a dab hand at mastering the “casual look” — what most of the rest of the world calls “dressed up” these days — by mixing in casual classic like Chukka boots:
Here is the rule of thumb for wearing a heavier (not necessarily just in suede) shoe or ankle boot: your trousers should be of a heavier material. Linen or poplin trousers call for something else entirely.