Late for my 2 cents, but here they are-can you pair the flowy skirt with a body con cami(top) and then a short sleeved tailored jacket of a summery kind? I think that added structure will make it look more Shannon like!

Just to confuse you more I also love the first skirt on you and don't see the unflattering aspect. Ok, you know how I dress and clearly I don't prioritize certain aspects of figure flattery (although of course I have my own issues with my mid-section), so take this as you like. I absolutely agree there is no need to wear it if you don't feel fab!

Funny at first I liked the fuller skirt, just maybe with a tucked in top to see more waist definition. But after seeing the pencil skirts, I vote pencil all the way. I am jealous of your pencil wearing prowess, I cannot wear them, they just never fit me right.

Just FYI for those who have suggested a body con top - that is not something I am comfortable with wearing so unfortunately that's out as an option.

I did try the skirt on last night quick with a black tank and then my black short sleeved fairly tailored blazer and my Doc Marcie boots. Definitely felt more like me and it did look better. Something to think about.

(Haven't read the comments).

TOTALLY think you rock fluid full skirts and do not need to stop wearing them. You look sensational in a pencil Shannon, and the proportions are very flattering. But the full skirt has it's own standout retro and elegant charm. Love #1.