Saturday Night Live turned mom jeans into a joke in 2003, and the high waist and relaxed seat have been quietly winning the argument ever since. This fall the shape comes straight, barrel and cropped, which means the top half of the outfit decides whether it reads 1989 or right now. Start with a pair from Róhe, Mother or Slvrlake, plus a plain black Polo Ralph Lauren leather belt to cinch the waist.

The contrast is the whole joke, and it lands. Citizens of Humanity's blue checked flannel shirt tucks into Agolde's dark 90's Pinch Waist jeans, then Tom Ford's velvet Selen pumps show up where you expected sneakers. A tan Tod's Tracollina bag keeps the colour story warm and stops the heel from tipping the outfit into cocktail territory.

Novelty knitwear and mom jeans share a lineage in the family photo album, which is exactly why they work together now. Dries Van Noten's burgundy Fair Isle sweater sits over Frame's cropped Bow Crop barrel jeans, and Isabel Marant's animal-print calf hair Fitza loafers add the odd detail that makes it look intentional. Nili Lotan's tan suede Cooper bag finishes it without adding another pattern.

This is the plainest formula in the story, and the one you will wear most. The Park's white Dina long-sleeve jersey tee, Khaite's cropped straight Abigail jeans and Aeyde's black Nomi ballet flats make a uniform, and Studio Nicholson's suede Reflection tote adds some texture. The cropped hem matters here, since a flash of ankle is what keeps a flat from looking sleepy.

A military-style jacket gives mom jeans some structure up top. McQueen's grey padded double-breasted wool jacket is the anchor, worn over Flore Flore's white ribbed Esmé tank and Calvin Klein Collection's dark straight jeans. Manolo Blahnik's black Chelata Chelsea boots keep it practical, and the outfit lands somewhere between off-duty officer and art-school graduate.

We like mom jeans most when the rest of the outfit is slightly too dressed up for them, whether that means a velvet pump or a double-breasted jacket. If you take one thing away, let it be that the fit at the waist matters more than the leg shape, so try a pair on with the belt and top you actually plan to wear. We would skip anything with heavy distressing, which drags the look straight back to the era it is borrowing from. One pair in a mid or dark wash covers almost every outfit here, and the black Róhe pair handles evenings. Loafers, flats, boots and a heel all work, which makes these one of the few jeans that get along with every shoe you own.