I happen to think that coordinating, rather than matching, works best. I rarely wear jackets, but I love to wear my dark olive jacket with a black shell and black skirt. I also have a navy wool jacket that originally came with a matching skirt. I loved that suit for a long time, but then I got taller, and the skirt became too short, so I replaced it with a longer skirt in a darker navy. It doesn’t match exactly, but I love it. Plus, during the summer, I once wore my black wrap top with an ivory shell and my favorite print skirt with the black background. I would’ve worn it again, but I started to show.
I also like the idea of a pinstripe jacket with a solid skirt.
To me, it just looks better when things aren’t so matchy-matchy.