Thanks for posting this outfit because it has really helped crystallize a couple of thoughts in my mind regarding how I'm going to wear this kind of ankle-length, casual pant. Here are the guidelines I'm going to follow for my outfits after seeing your examples:
Ankle pants look good with some skin showing at the bottom; that's why pumps and ballet-style or loafer flats work. Showing skin focuses attention on the ankle area.
If the foot and ankle is covered, continuing the color of the pant is flattering because it lengthens the leg line. Wearing a contrasting color is trickier. It probably works best if the color of the closed shoe is bookended somewhere else in the outfit or by the person's hair.
Rolling the pant leg is a trick you can use to show some skin. It probably takes some fiddling and you might have to go with something that is just flattering enough. It's worth trying if the shoe covers most of the foot but doesn't match the pant or isn't obviously bookending, like your nude bootie.
Unless you are deliberately going for a dressy shoe/casual bottom look (like a youthful blogger wearing ripped denim shorts and sequined stilettos?), it's safer to match a casual pant with a chunkier, or more casual, shoe.
Leopard, and probably other animal prints, are versatile because they can look casual, or dressy, depending on what is happening in the rest of the outfit.
That's what I learned from this Outfit Lab. Note that my guidelines will work for ME, but might not be applicable to you, or other fabbers.
And, by the way, I think the fit of those casual pants is perfect--not too tight or too loose. Same for the sweater. Modern, a bit slouchy, and very flattering. You don't have to consider that a compliment, because that's just my analytical, cool-headed observation.