I'm naturally around a medium contrast, but I've found I'm pretty happy wearing outfits with all kinds of contrast levels, as long as the colours/neutrals I'm mixing are flattering to me. So I'm not going to wear optic white & saturated black, because those colours overpower me, but in my last outfit, for instance, I combined a deep navy (softened a bit because it was velvet) with a soft white/light grey striped tee, which is high contrast for me. Here's my outfit pic in grayscale, although of course cameras don't capture tones in the same way as our eyes, and the b&w processing changes it even more, so my trousers & scarf look a bit darker/more saturated here than in real life.
To my taste, low contrast combinations feel most soft and romantic, particularly if they're also low contrast with my own colouring (vs just with each other...so a dark purple top & navy bottoms would be low contrast with themselves but high contrast with my skin), medium contrast are probably my most used option, because I like to have a break in the outfit at my waist, and high contrast (to each other) gives me a bit of extra drama. They all work, if I make sure the colours I'm combining flatter me (in my case, that means sticking with muted shades, as I'm easily overpowered by stronger colours).
I do think this is also related to bookending/repeating colours. Since my hair is a medium tone, it's *easiest* for me to wear medium values on bottom, as I'm automatically echoing them. When I opt for very dark or light values instead, I try to echo that colour somewhere up top. With light values, I can echo it with my skin if I'm showing any (not in the depths of winter, LOL). With dark values, I don't have any natural options. Hence my eternal hunt for medium value, cool toned, non-suede shoes. Sigh.
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