Denim and heels is a specific combination and most jeans are not cut for it. The problem is the hem. A jean hemmed for a flat will sit too short over a heel and expose the ankle awkwardly, and a jean hemmed for a heel will drag on the floor with a flat. That means the pairs that genuinely work with heels are either long enough to cover the shoe almost entirely, which suits a wide or bootcut leg, or deliberately cropped above the ankle, which suits a straight leg. The awkward middle is a full length straight leg breaking on the top of the foot, which reads as an accident. Rise matters too, since a high rise lengthens the leg and a low rise fights the height the shoe is adding.

A wide leg or bootcut jean wants a heel with some height, ideally covered entirely by the hem so the effect is one continuous line, and a block heel or a wedge is more stable under that much fabric than a stiletto. A straight leg cropped at the ankle suits a pointed pump or a mule, because the exposed ankle keeps the proportion light. A slim or tapered jean is the easiest with a heeled sandal or a knee boot, since there is no volume competing at the ankle. Where it breaks down is a very stiff rigid denim with a delicate shoe, because the weight of the cloth makes the shoe look flimsy. A softer denim with some drape flatters a finer heel considerably more.

The single change that made this work for us was owning one pair of jeans hemmed specifically for heels and never wearing them with flats. It sounds precious and it is the only reliable fix, because the alternative is a compromise length that suits neither. Beyond that we look for a mid to dark wash and minimal distressing, since a heel already pushes the outfit towards dressed and a rip pulls hard the other way. Rigid denim holds a crease and looks sharper standing still, while a little stretch is kinder over an evening. If you take one thing away, buy the shoe first and hem the jeans to it, and denim with heels stops looking like a compromise.