Breaking rules with long skirts

I take guidelines for figure flattery seriously. Like Academichic, Fashion for Nerds, and Already Pretty's great tutorials. I love to learn new things, even now as learning and teaching is my bread and butter. But sometimes I want to bend the rules. Sometimes I just want to fun and hope that I don't look like a bag lady. The Olson twins (almost) single-handedly made unflattering, unconventional, and less shapely layered outfits (with killer shoes) one of the most important trends of the 2000s, so there is definitely an art to non-figure flattery.
Today, in addition to regular at home work, we are going to downtown Brooklyn for errands, and then the Upper East Side for his and her haircuts. This means train time and lots of walking. I know that this outfit would look more flattering with my cognac boots, or if I lopped 3-4 inches off the skirt. But I kind of like the weirdness factor of the combat boots. I also realize that I have stumpified my legs. I think that I am OK with that. The skirt is wool and uber warm and it will keep the cold off my legs (with the leggings) as I walk around uptown, as my jeans and pants drying on a rack.

It's a little monochromatic, but I did this intentionally so I could emphasize the beautiful camel color of the vintage coat. The skirt is actually grey, black, and camel plaid, so I thought it was perfect.

I am also breaking my (self-imposed) rule of trying to be more colorful, but sometimes I just like to be head to toe in neutrals. I still don't really know what exactly qualifies as neutrals (I thought camel was a color. See a great discussion here).

close up of the skirt plaid

Do you ever dress in a way that you know doesn't flatter you, either to have fun or just to try things out?

I'm actually this happy about my new (to me) coat, tailored at the local dry cleaner

Coat: Collecther, $42
Leggings, Target, $5
Boots, Mia, $85
Skirt: Pendleton, vintage, via ebay ($7 including shipping) (the other half of this blazer)
Sweater: Espirt, $30
Knit hat: Brooklyn Industries, $19