I think it's a question of proportion, Delurked. Which is hard to make sense of since many women know that dresses and skirts just at, on, or below the knee are a slam dunk for them.
But here's my theory, based on my own body type modifiers. My legs are overall about equal or just slightly shorter than my torso. So longer shorts can seem to cut the clothed portion of my body in half. And this can shorten my legs visually and look awkward.
And knee to ankle is shorter on me than my upper legs. With my relatively shorter calves, longer shorts can make me look and feel "stumpy" without a heel (and when I am wearing casual shorts, I usually don't want to wear a heel.) Those with relatively longer calves obviously don't have that problem.
Another issue for me, personally, is that I have a long rise, and when wearing pants/ shorts that is emphasized more than it is in a dress. So without careful styling, shorts at this length can give me a shorter-legged appearance. I look longer legged in shorter shorts.
Toning tops to shorts, choosing footwear more mindfully, and being careful that the longer shorts narrow at the bottom vs. flare out widely (which looks awful on me) can help mitigate this. But on casual days I don't always have the wherewithal to go through all of this!
In #1 and #2, I'm wearing a wedge sandal. But you can see how my legs still look short with that untucked longer top in #1. (I stopped wearing that top untucked and wore it semi-tucked, which helped a lot. You can see how tucking and semi-tucking lengthens the leg line for me in 5, 6, and 8 as well.)
In #3 I have a flat sandal with a lower vamp, which was more flattering. But the sandal wouldn't stay on my foot, alas. Darn.
In #4 and #6, I have a one inch heeled wedge, shoes low contrast to skin. This helps! Of course in #4 and #6 I also have shorter shorts on!
#5 is an outlier because, pointed heels of 2 inches, which I would never wear in real life with shorts for more than an hour.
#7 is a relatively low contrast flat sneaker. But shorter shorts. Different proportion.
#8 is a one inch heel sandal. But that semi-tuck, which shifts things a bit.
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