In 1935 an Esquire reporter noticed that the well-dressed men in Palm Beach were all wearing the same slip-on. The magazine put a New York menswear store in touch with G.H. Bass, the Maine moccasin maker, and in 1936 the Weejun was born: a Norwegian farm shoe, rebuilt with a strap stitched across the instep. The name is a playful shortening of "Norwegian". I like that the most famous loafer in America started as a joke about geography.

Students later tucked coins into the diamond cutout of that strap, and the penny loafer got its name. Esquire is careful to say "perhaps" about the payphone story, and so am I. What I trust is the shape: a moc toe, a strap, a flat sole, nothing to tie. That is why black loafers work in October, when you want something that goes with knit tights, wool trousers and a coat without a second thought.

Start the edit with the plain penny. The Frye Faith is polished black leather with raised stitching, the kind of pair I would wear with cuffed denim and a gray sweater. The Vince Teo is the sleeker one, with a slim keeper and a streamlined profile, so it sits well under tailored trousers. Tod's makes its penny loafer in Italy with a pebbled rubber sole, which I would choose for walking around a city on a wet day. The aeyde Aldous has a scalloped keeper and a pronounced moc toe, and it is the one I would put with a midi skirt.

Before you buy, press the keeper with your thumb. It should feel sewn in, not glued on, and the heel counter should hold its shape when you squeeze it. If you want one pair for the whole season, pick the polish you can live with, because black leather forgives a lot of weather.

Bass itself now sells lug-sole Weejuns, including the Whitney Super Lug, which tells you the chunky revival reached the original. Vogue described the Prada version as a polished take on the stomper boots of the previous seasons, and that sentence explains the whole appeal. It is a dress shoe with a boot sole under it.

The Tory Burch Classic Lug has glossy black leather with gold logo hardware, and I would wear it with straight jeans and white socks. The Veronica Beard Penny Lug is high shine on a rugged sole, a good match for a pleated skirt and a dark knit. The Stuart Weitzman Hudson Lite keeps the lug light, which is the detail I would look for if platforms make you nervous. The Vince Siena mixes suede and smooth leather on a block heel, so it works for people who want height without a stiletto.

The rag & bone Bedford has an OrthoLite footbed, which matters if your day is long. The Paul Green Carmel is black suede on a grippy platform, and I would wear it on a rainy weekend when leather would spot.

The fitting-room test: walk down a hall and listen. A heavy sole that slaps the floor is too stiff, and a heel that slips means the last is too wide for you. Also bend the shoe by hand at the ball. A lug sole should flex there, even if it looks like a brick.

What I would skip: a lug sole with a very high platform if you plan to wear it with cropped trousers all day. The proportions get heavy fast.

In 1953 Aldo Gucci added a metal snaffle bit across the vamp of a sleek leather loafer, a nod to a horse's bridle. GQ points out that the name comes from equestrian culture, not from riding boots, and I find that oddly reassuring. You do not need a stable. You need a hinge of gold on a quiet black shoe.

The Gucci Horsebit 1953 is black calfskin with gleaming hardware, the original shape. The Gucci Jordaan is slimmer, with an apron toe, and I would wear it under a long camel coat. Both are the real thing, so treat them as a long game and keep them for the closet you actually use.

Every other pair here does the same trick in a calmer register. The Cole Haan Emeryn is a driving loafer with a polished bit, which I would pair with a gray flannel skirt. The Clarks Orianna puts classic bit hardware on a lug sole. The Sofft Prewitt has brushed metal hardware on a patent-finish flat, and the Comfortiva Ester adds a cushioned collar. The Munro Colleen and Paul Green Faith have the wider toe boxes in the group.

Check how the bit is attached. It should sit centered, flat against the vamp, with no rattle. Brushed metal looks softer next to wool, while shiny gold looks sharper with a black suit.

What I would skip: a bit that is oversized for the shoe. If it is wider than the vamp, it reads as a costume.

Patent is the cleaner one. The Marc Joseph New York East Village and the Franco Sarto Carolynn are glossy black penny styles that I would wear with a white shirt and straight trousers, the preppy-to-professional look. The ECCO Dress Classic 15 adds a tassel to a flat patent shoe, a small joke on formality. The Coach Leah Patent Platform is the loud one, with a logo strap on a lug platform, and it turns jeans into an outfit.

Suede is the soft counterpart. The Lauren Ralph Lauren Barnsbury is driving-style suede with a small gold logo plaque, very good with a corduroy skirt. The Free People Lana is relaxed in an unlined suede upper, a weekend shoe. The Amie Rafa York has gathered pleating on the apron, so it is the pair for people who like a loafer with some drama. The André Assous Phoebe is velvety black suede with a shearling lining, which makes it my October pick for cold ankles.

Patent wipes clean with a damp cloth, and that is its whole practical argument. Suede does not forgive water, so a protector spray before the first wear and a suede brush after are not optional.

Test patent by flexing the toe: the finish should bend without creasing sharply or cracking. Test suede by rubbing it with your thumb. The nap should change color, then settle back.

What I would skip: black suede for a slushy commute, however nice the lining is.

This is the group for people who like the look of a loafer but hate pushing a heel into a shoe at 8 a.m. Take the slip-on idea one step further and take away the back.

The Rothy's Double Bit Loafer Mule is a flexible knit with a gold double bit and an open back, an easy one for a long day. The Sam Edelman Louella has a penny keeper and a loafer-style topline on a leather mule, while the Johnston & Murphy Isabel and Jeffrey Campbell Goddard are the straighter penny mules. The Marc Fisher LTD Jaynie is a glossy ruched almond toe that I would pair with wide-leg trousers.

Then there are the slingbacks. The Tory Burch Classic Penny Slingback has an adjustable strap on a glossy black penny shape, and the Vince Camuto Grinie puts that same idea on a block heel with a gold buckle. The DKNY Caxine adds kiltie fringe and brogue perforations to a pointed black patent flat, the fussiest and the most fun here.

Test the back. A mule should stay on without clenching your toes, and a slingback strap should land on the narrowest part of the heel, not slide down. Take a few steps on a hard floor, because a mule that clacks is a mule you will stop wearing.

Style note for fall: a dark sock or sheer black tights bridge the gap with a slingback. Bare ankles can wait for spring.

What I would skip: an open-back mule on a rainy day. The wet hem and the wet heel are a bad pairing.

Pick the sole first. Flat and slim for trousers, lug if you walk or want a boot feeling, a block heel if you need height. The rest is a question of finish: leather for rain, suede for dry days, patent for work.

Then choose the detail. A penny keeper is the quiet option, a bit is the dressed one, and a slingback is for people who want the loafer to move a little. Whatever you pick, a good black loafer should look right with socks, tights and bare legs.

I keep going back to that 1936 shoe. It was a Norwegian slip-on with a strap and a slot, and ninety years of good shoes still follow its outline.