Go for Height// I found that the dress and jeans look worked best with heels. Wearing flats made the whole outfit look too bulky.
Layer in Varying Lengths // For this look, dresses with a bit shorter of a hem work the best. Compliment the short dress with a long coat or sweater. The contrast in length will help to keep the whole outfit streamlined.
Cinch It In// The dress with jeans look is not good with flowey dresses. You'll want a dress that has structure and form. However, if you absolutely must use a flowey dress, I recommend cinching it in at the waist with a chunky belt. And if the dress isn't flowey, well, still use a belt to break the look up.
Have you ever tried wearing a dress with jeans?