Two Grey Skirts

I have a grey skirt that I like pretty well. It is wool flannel with inside-out seams, a nice detail. It is a good length, A-line, but the fabric is slightly stiff. Not a lot of swish or drape to this skirt, so when Talbot's marked down their grey knife-pleat skirt by 50%, I ordered one.

Here is the same outfit worn with each skirt. I wanted to wear grey with brown (my new Born boots), and pulled out this little cardigan my sister-in-law gave me two Christmases ago.

Riley matches perfectly.

Here's the thing - it took some doing to put this outfit together. The cardigan has just enough taupe in it to pick up on the brown boots, but it is a little tight and I rarely wear it. I could have worn a dark brown tee and a brown jacket as well, but the look would have been a little flat, I suspect. 

I love medium to charcoal grey, but it can be tricky. I tried a purple blazer and felt like I was on my way to Hogwarts. I just needed a rep scarf to complete the look. Navy and medium grey make me feel like airport security. I actually like shades of taupe and brown the best. Bright green and hot pink also work well with grey. So, no "serious", dark colors, and a blazer with a pleated skirt reads too prep school, at least on me. This is a cute possibility:

I'm trying not to have two of the same thing in my closet, especially when I don't have a multitude of items to wear with it - but I really like those swirly pleats. (I also bought this skirt in emerald green and it is AWESOME.)

Comments, thoughts, questions?