Exactly - I look way skinnier in dresses with flattering shapes!
Actually, I need to write Mad Men a thank you note - I always thought I didn’t look good in pencil skirts because they made me self conscious about my shape, but Christina Hendricks and I have similar bodies and she rocks the hell out of them. I tried a bunch on until I found some that fit me and I look fantastic in them.
I suppose I could wear a dress more often but I only own 3 to start, and it depends on what i’m doing that day, because I’m not going to fuck up what nice things i DO have by wearing them whenever.
I have skirts but I don’t know that I feel very comfortable in them… I worry that i’m going to spill something or trip on my own two feet. I’d have to consciously pick out a skirt and top and go to the library or something, and not reach for my jeans like i always do.
And I’m sure heels feel the same way about you.
Any time I can 
Particularly for weddings (hats!), funerals, the “theatah”.
I wore a pair of tailored capris, a lightweight twin set and some nice sandals to a graduation barbecue and was asked repeatedly if I were going “someplace fancy” afterwards. I kept thinking “No, if I were going someplace fancy, I wouldn’t be wearing capris”. 
UT
Two times in my life, once a funeral, once a wedding, I was aghast at the attire of specific individuals.
When my great aunt died, her son-in-law, husband to her only child, showed up at the funeral in pilly khaki polyester pants, a polo shirt, and ratty, worn-down hushpuppies. Then again, maybe it was appropriate, as he was always a slob…
At my daughter’s wedding, her future-ex-brother-in-law showed up in cargo shorts, a bright yellow polo shirt, and boat shoes with no socks. He looked stunning in the family photo. (We’ll not get into how he RSVP’d for 5, then left his wife and kids home.)
I guess each instance spoke volumes about the individuals.
See, this is what kills me. Because I also look slimmer in skirts and dresses. There’s just something about exposing my skin that makes me feel very insecure. I have one visible spider vein on the inside of my ankle that looks like a bruise. Other than that, no visible spider or varicose veins. My legs are pale, but smooth and even-toned and there’s minimal cellulite on the part that shows. So it’s not that my legs are hideous; it’s definitely a mental issue.
I wore a dress in front of my husband’s family for the first time since 2006 this weekend. Everyone asked me if I’d lost weight. I think I’m going to have to suck it up and just start wearing more skirts and dresses. Of course, it sucks that I’ve come to this conclusion just as fall has started.
Pairing your skirts and dresses (especially longer ones in thicker fabric) with nice warm tights would be a good way to ease into wearing them more often.