The mistake is buying a jumper dress a size up because the wool looks like it needs room, then wondering why you're drowning in it by lunchtime. Knitted fabric already has give. A jumper dress cut too generously doesn't relax into you, it just hangs, and you end up looking like you're wearing a jumper that lost an argument with gravity.
A decent one earns its months back slowly. Worn and washed properly, a good knit dress will pill a bit at the inner thigh where tights rub and under the arms where bags sit, but it won't go baggy at the knees or stretch out at the neckline into a sad scoop. Hand wash or a wool cycle, lay it flat to dry rather than hanging it, because a wet knit on a hanger will grow two inches at the shoulders and never quite forgive you. Cheap acrylic versions do the opposite of ageing well, they bobble everywhere within weeks and start looking tired almost immediately, like the jumper equivalent of a carpet that's seen too much foot traffic. On the clashing front, skip anything with its own strong texture underneath, a chunky cable knit dress over a ribbed polo neck just reads as too much wool in one outfit, and thick tights with a thick dress can make your legs disappear entirely, which is rarely the look you were going for.
For fit, the shoulder seam matters more than people think it does with knitwear, because a dropped shoulder on a jumper dress should be a choice, not an accident caused by sizing up. Check where the dress hits on you specifically, not on the model, since jumper dresses vary wildly between mid thigh and ankle depending on how much they've stretched on the hanger before you even try them. Watch the waist, too many of these are a straight tube that adds bulk exactly where you don't want it, so a slight shape or a belt option is worth seeking out. The difference between a good one and a disappointing one usually comes down to the yarn and the finishing, a proper blend with some wool or cashmere content holds its structure and drapes rather than clings, while a cheap all acrylic knit goes thin and see through at the stretch points within a season. Check the ribbing at the cuffs and hem too, good ribbing snaps back, poor ribbing just droops.
It's a brilliant option for looking pulled together with almost no effort, but it will never be your most flattering silhouette on a day you want real structure, and that's just the nature of the thing.