i asked something like this a couple weeks back. most of the suggestions people gave me were wear with shorts and nice shoes, like platform heels wedges whatever, and pair with like a comfy tee and accessories there is even a fellow chictopian who wears her over knees with garters and shorts. its refreshing!! i love love love it!!posted about 5 years ago
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I love knee socks and over-the-knees (scrunched down) worn with shorts. Like baggy cargo shorts or cuffed mid-length khaki shorts. The fine weight ones look nice with a skirts and sandals. Knee socks are also great with boots.
I think as long as you avoid short skirts, particularly close-fitting short skirts you can wear them without looking trashy. Keeping the rest of your outfit either classic or simple and fun (not aiming for “sexy”) also puts you in the safe zone with knee highs.posted about 5 years ago
I think they work with a variety of looks—mainly experimentation will yield the answer.
They can look nice with a sack dress, or 60s style shift.