How To Pull Off Pencil Skirts and Flats (Even For Petites)


We had a blast at the World War Two Weekend in Reading, PA this past weekend.  (For more deets on the event, see my full coverage here.  It’s pretty amazing.)  But dressing for the weekend is always a challenge:  it’s hot, it’s sunny, I’m on my feet all day, and then at night…..there’s a swing band and dance party.  To make matters worse, most of the other attendees arrive in full 1940’s costume.  Every year they look GORGEOUS and glamorous, and that level of dedication truly makes the weekend feel like stepping back in time.


So. I wanted to wear something comfortable, but something that could hang with all of the pin-up girl glamour (although a few women came dressed as Rosie the Riveter which was awesome).  Inspired by Cam “grunging” her pencil skirt (bless her preppy little heart), I used Cam’s grunge to make mine…glam?

But here’s the thing:  Cams is tall. I am not.


Ballet flats would lengthen my legs, but I stuck to Saltwaters because the style felt a bit more retro.  I’m seriously digging how they look with a ladylike pencil skirt.

The one key to this look (at least for me) was the shirt proportion:  it’s tucked…HIGH on my waist.


I’m wearing the skirt at my natural waist, and fully tucked in the top ( instead of my typical half-tuck).

Want to compare?  Last summer, I wore almost the exact same outfit….the major difference was that the skirt was worn down on my hips, and the tshirt was half-tucked and slouchy.

I think the difference is kind of amazing.


outfit details

top: J.Crew Carrie cami bought several sizes big last summer (yup – it was on clearance).  The stripes are long gone, but Express’ Striped Barcelona Cami is similar, and a better buy (on sale for $29, plus an additional 20% off of that right now).

skirt: Weston Wear (last season)….but this high-waist midi skirt by Leith is virtually identical, just a tad longer.  (Spoiler alert – you’ll be seeing it on TME next week.  The slightly longer length is insanely flattering, even on my short self.)

shoes: Saltwater sandals in red 

sunglasses: Ray-ban Folding Wayfarer in Matte Blue

bag: Makr Farm Rucksack

bra: Free People Galloon Lace Racerback in silver

lips:  Tarte Matte Liptint in Fiery (put it on in the morning, and only reapplied once)

This outfit was perfect – easy to move, easy to sit, not too hot, and I felt so ladylike and pretty.  A total win.

Also a win?  This whole freaking WWII weekend.  Man, we had a good time.


One of the re-enactors, “Staff Sargent Nichols,” reached out last week and invited the boys to stop by for a special tour of the 1st Infantry Division.


Isn’t that awesome???

Also, my boys’ biggest nemesis was BACK:


Adorable.  I just can’t even.  (If you missed it….pics from last year’s event.)