Depends, where the contrast comes from:-).
For ex. I am a low contrast girl myself, but nowadays love me a more dramatic, hIgh contrast (with my skin and hair) outfit. Also, darker/brighter colors feels like contouring my softer, ageing body, or so.
OTOH I prefer my outfits to be mostly a column of color, if you know what I mean. In general, I pay attention to have a column of colors for 80% and only perhaps 20% of the contrasted one in one outfit!.
This can be achieved by layering(when only a small amount of the other color will peak out from under) or with some patterns (the bigger asymetric print, aka.a graphic prints came to my mind), too.
But, usually I DO prefer these colors to be of a big contrast between themselves, and with myself, too.

(&I will to read the comments later)

Interesting Sterling! I tend to do the opposite, dress in higher contrast for gloomy weather and lower contrast for pretty weather. I am very strongly affected by weather so I try my best to keep chipper when it's gloomy (which is a looooong period where I live)

And I do a weird combination....I dress in darker outfits for the most part in winter....which is high contrast to my pale, low contrast self. But there is less contrast in the outfits themselves. This is largely for practical reasons, by the way...not necessarily preference.

Meanwhile, if given my druthers, I'll put a bright (and high contrast) coat over top of all those darks!

I go higher contrast and brighter in summer's more constant light.

In general, sign me on as someone who, like Angie, does both. I love white out (which is low contrast to me and low contrast in itself). I also love ink-out (high contrast to me, low contrast in itself). And equally l like higher contrast outfits...or mixed mid-tones like grey with berries or a mid-blue or denim with taupe.

I am most flattered by mid tones -- blues, berries, and a soft charcoal grey. But I'm most enlivened by a higher contrast outfit with a hit of ink-and-white along with a hit of colour.

So it all depends on your goal, I guess.

So much wisdom here. Sometimes the guidelines can point out why an outfit isn't working but generally I'd not take them too seriously. Like Suz, I wear midtones best as long as they are clear and not murky. They are also not high contrast with anything. But I also feel enlivened by more contrast. Sometimes it works best to do this with texture or print mixing or a mix of casual with dressy, hard with soft, etc. rather than color.

Sterling, also to me there is a semantics issue that your example brings up because you mentioned contrast between top & bottom. An ensemble could be high-contrast somewhere within it--like a print skirt with several highly contrasting colors, lights and darks, but a "low-contrast" skin-hair-color person could pair that with a top that picked up a color and depth of color that was low-contrast with her own coloring. In contrast (!), a person with pale skin and very dark hair and eyes & wearing red lip color could wear black on top & bottom and that's high-contrast with coloring but monochromatic as an ensemble.

It's really quite interesting sometimes to try to tell what exactly about clothing "color" either "feels right" or is most flattering because it seems to be a mix of cool vs warm, contrast, color "depth" or tone, undertones and all that. And so a lot of that is more relevant to colors worn near the face, and then the rest of the outfit has to make some kind of sense with that, but there is more flexibility (assuming "color flattery" is the goal for that ensemble).

I'm no color theory expert and don't even know how best to describe some versions of colors, but I find that "bright" colors don't look as good on me. So though I have cooler-toned palette and am medium-high contrast and look best in a lot of fairly dark colors, if a color has a lot of "glow" it's often too much for me even if it seems it ought to work. OTOH most pale dusty colors are awful. Not sure if that means I am "soft winter", or "deep summer" or what. It does help narrow down things that aren't worth ordering online, but still I will try a variety of colors in my general palette since if often "just depends".