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I do pencil skirts a lot too - my favorite is from J Crew.

I style with:
1) a tucked-in loose blouse
2) a tank with a mostly buttoned cardigan
3) a tucked in tighter t, cardigan, and belt outside
4) a tucked-in shell and blazer

During the winter, I do tights and boots; during the summer, I do heels or heeled, dressier sandals.

I'm short so if I wear pencil skirts I must wear heels or I look even worse than that girl!

I used to wear mine with button downs tucked in, with cardigans and sweater vests.

Kinda like these pics but cuter

I see pencil skirts as a basic that I can wear just about anything with. I love Loft and Jcrew pencils. I have a couple of the jersey kind that are super comfy too!

Floaty blouses, cardigans and shells, basic tees with scarf/statement necklace, belted sweaters, peplum tops, blazers, etc etc etc. The list goes on and on!

I would only put a pencil skirt on in a work setting, it's just not my idea of casual clothes. I wear them with stocking and heels/elegant boots and usually a blazer.

@coopsmama: it is definitely powerful!

@Mrs. Pen: I have a few jersey/ponte pencil skirts, one of them is actually similarly striped!

I haven't worn it yet, it's a spring skirt, but you're right, I'd wear it to church, maybe to a baby shower, lunch date. I tend to think about practicality at the playground, lol.

I wear pencil skirts all the time. Alllll the time. And since I'm on my feet a lot at work, I pretty much never wear heels any more. Boots of some kind in the winter and ballet flats or sandals in warm weather. I also rarely tuck in shirts.

We walk so much where I live that it's far more common to see women wearing flats with their skirts than anything else. So I don't feel strange not wearing heels.

And I think the fit of the skirt and top are more important than the shoe, as far as if it's an attractive look. First picture is cute to me and fits well--second picture, the skirt and top are both ill fitting.