I think this is a question that no one asks and/or answers
I'll tell you how I envision leather legging looks and IMO they are foolproof
I tuck the tee like halfway in just messily enough
btw, the slouchy black Topshop long sleeve tee can be worn half tucked in (exactly like the model) and be worn sans blazer for an uber relaxed vibe
a 3rd way is to wear black ballerina flats with either the cardigan or oversized tee and blazer look (but it's harder to find the perfect ballerinas)
an oversized chunky knit cardigan that covers all of your tushie
when the cardigan covers your whole tush, I think it looks best with black leather leggings and black pointed toe heeled boots/booties
AND I think a cardigan works best with the boot look and a chunky regular knit looks best with a pointed pump (non-boot) look
wear a sleek fitted black tee/turtleneck underneath either of these 2 cardis