In 1873 a Reno tailor named Jacob Davis had an idea: copper rivets to reinforce the points of strain on work pants, like the pocket corners and the base of the button fly. He and Levi Strauss received U.S. patent 139,121 on May 20, 1873, and the blue jean was on its way. More than 150 years on, jeans are still the easy half of the outfit. The hard half is the feet.

So here is how I think about what shoes to wear with jeans. Look at the hem first. A cropped or straight leg shows the ankle, so a flat or a loafer reads as a decision. A wide or flared leg needs a little height so the denim does not drag. A skinny leg tucks into a knee boot. Harper's Bazaar put the straight-leg rule neatly: a slightly masculine-leaning shoe such as the loafer grounds that slim line.

Start the edit with flats, the quietest option. The Reva Travel ballet flat in black folds up for a weekend bag, and the Dany in black leather has a pleated square toe and a beaded toggle that gives a plain jean something to look at. The Blaine has a taller, covered topline, which I would want with a cuffed jean. The Nia adds a small toe bow and a stretchy topline, so it stays put. For something less polished, the Mikela Mary Jane in tan suede has a buckle strap and a perforated upper.

One practical note: a Mary Jane strap gets lost under a wide hem, so keep it for jeans that stop at the ankle. Before you buy, stand in the shoe with the jeans on and check that the hem skims the top of it, with a small gap of ankle showing.

The loafer has a date you can check: G.H. Bass first made its Weejuns in 1936, and the penny loafer has barely changed since. The Coach Astor is the black leather version, with moc-toe stitching and a small C on the strap. It is the plainest shape in the edit and the one I would try first with a straight, slightly cropped jean.

Harper's Bazaar suggests mirroring the clean lines of a cropped leg with polished loafers, and using the extra ankle space for a pair of socks. I like that. A burgundy sock under the Loraine, the woven burgundy horsebit with a flat sole, looks deliberate. The Classic Loafer in red, with gold hardware and a serrated topline, is louder and would be the one pair I wear with plain dark denim.

For wide-leg jeans, go heavier. The Leah in black patent and the Penny Lug both sit on chunky lug soles, which give a loose hem something to land on, and the Bryant has a penny strap and a ruched, slouchy heel. The Tiggy is a smooth black leather penny loafer on a thick sole with a ridged edge, a quiet match for a smooth, dark jean. The James in camel suede is slim and almond-toed, and the brand says to size down if you are between sizes.

Try the loafer on with the jeans you will wear. The hem should sit at the ankle bone or just clear the shoe, never bunched over the tongue.

What I would skip: a thin, flat loafer under a very long wide-leg, because the hem will swallow it.

Wide and flared denim is where flats let you down. Red magazine's fashion director says a loose, slouchy jean, unless you are very tall, requires a heel to help the drape. The same goes for a flare: the point of the boot is to lift the hem so it skims the floor and does not drag through October puddles.

That is why every bootie in this edit has a heel. The Saige in black suede has a 2 3/4 in heel and a slender square toe, and the Bacari in black leather has the same height with a back zip. The Wally in brown suede has a slender toe and a slim, low heel, and the Sebastian in dark brown suede has a pointed toe on a kitten heel. If you want more bite, the Mikki in burgundy has a pointed toe and a 3 1/4 in heel, and the Houston II is sharp and polished in black leather on a slim heel.

Pointed toes help here. A flare opens wide at the bottom, and a pointed toe peeking out gives the leg a longer line. The Tory Burch T-Lock boot and the Brooke II in calfskin add gold hardware to a black pair.

Test it at home: put the boot on, stand in front of a mirror, and look for a hem that stops a half inch above the floor. Then walk a few steps and check that it does not catch on the heel.

What I would skip: a flat, round-toed boot under a full flare, which makes the hem look as if it was never finished.

Skinny jeans are back, and Harper's Bazaar calls tucking them into knee-high boots the freshest styling hack. It makes sense in October: the slim leg disappears into the shaft without a lump, and you get a long, clean line from hip to heel.

The test is the shaft. The Porter in black suede has a 15 1/4 in shaft and a 13 3/4 in calf circumference, the Pace in tobacco suede is 16 1/4 in with a 15 1/4 in calf, and the Tory Burch T Lock riding boot is 15 1/4 in and 15 in around. Measure your calf with a tape and compare, then sit down in them, because a stiff shaft pinches at the back of the knee.

Not every pair needs a heel. The Wally from STAUD is a sleek black lambskin boot made in Portugal with a barely-there heel, and the Remy is a slim black leather boot with a narrow square toe and a low, slim heel. The Callena is a tall black leather boot with a pointed toe and a slim heel, and the Brion has a V-notched topline that is a neat contrast to a plain jean. The Jendi is a slim 2 1/2 in stacked heel that goes with almost everything.

Tuck the jean in smoothly and keep the ankle seam flat. A thin sock helps.

What I would skip: a tall boot with a wide-leg jean, because the volume will bunch around the shaft.

Harper's Bazaar suggests slim-profile trainers for flares, naming the Puma Speedcat, and that is the pairing I would try on a Saturday. A low sneaker does not fight the hem, and the flare falls over it the way it should.

Both Speedcats here are low racers: the OG in light blue suede with a black formstrip and a gum sole, and the Premium in gray suede and mesh with a silver formstrip. The Samba OG in black has an extralow profile and cream serrated stripes, and the Gazelle Indoor in brown with blue stripes is the one I would put under a straight jean, rolled once. Veja's Campo in tan suede has a cream V and an off-white sole, while the Volley O.T. in powder blue has broguing on the suede overlays. The 327 has a 70s-throwback running shape and an oversized N, and the Club C 85 in silver is the pair I would wear with dark denim for a bit of shine.

Check the sole before you pick a pair. A slim profile works because the sole is thin, so a chunky one would swallow a cropped hem. Veja says the Campo has chrome-free leather, and its soles use wild Amazonian rubber.

What I would skip: a bulky running sneaker with a full-length straight jean, since the shoe fights the clean line of the leg.

If I had one pair of jeans and one weekend, I would start with the hem. Cropped or straight, I would reach for a loafer, and wide or flared, a heeled bootie. For a skinny leg, I would tuck it into a knee boot with the right shaft.

Then I would add a flat for the days I want quiet, and a slim sneaker for the days I do not want to think about it.

Davis wanted a pocket that would not tear. Everything after is just deciding where the denim stops.