I've always regarded loafer-wearing men with some suspicion. This is due in no small part to the fact that Italian men favour loafers, and I grew up with the erroneous impression that Italian men are great philanderers (maybe they are, but the ones I know are pretty faithful - it's the women who need watching). The idea was that, as loafers are quick and easy to get on and off, they were worn by men who needed shoes that were easy to get on and off. In other words, men who had to get dressed in a hurry on finding they needed to make a quick getaway. Brogues don't allow for fast exits out of windows.
Thus, because I spend an inordinate amount of time looking at what people are wearing, and judging them for it, I've always mentally labelled men who wear loafers with the word "shifty". It's wrong of me, I know, but there you go.
Loafers were big in the 1980s, especially those heinous ones with big fringes and tassles, which are, unfortunately, once again very fashionable this year. After some wear, and little attention (few people take good care of their shoes), a loafer splays out and looks untidy, because it doesn't have any laces to corset it back together. Personally, I would advise against wearing loafers that look too coarse - that means no cheap leather, no thick raised "piecrust", no chunky tassles or fringing. Really, just avoid buying "value" loafers, because this is one shoe that shows how much, or little, you've paid. Stripped of detail, loafers are very probably the perfect flat shoe, even if I still can't get my head round men wearing them (so are pumps, but the pump doesn't have the variety that a loafer can give you).
The Gucci loafer, with equestrian-themed metal snaffle, is a bestselling classic that you can still buy; ditto Salvatore Ferragamo's version, which has a chunky chain across it. A fashionable friend in the mid-1980s once spent a silly amount of money buying Gucci loafers in every finish she could find: black leather, black suede, black patent and, finally, decadent white leather.
The driving shoe (which Tod's makes so well, if expensively) is a good way to wear loafers if you prefer something with a bit of a sporty feel. The 133 rubber pebbles on the sole and heel help cushion your foot from, well, life in general.
I managed to procure two prototype pairs of Joe Casely-Hayford loafers in 1989, which served me well for the best part of two decades. They had a horsehair apron, patent surround (patent leather is a great way to make a flat shoe glamorous) and the strap had the four suits of a pack of playing cards embossed upon them. But what made them really beautiful was that they were elongated, with a squared-off toe; they looked fabulous peeking out of a pair of trousers, yet were blissfully comfortable.
I'm not sure what more one could ask of a shoe.