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.)




  1. Question about midi skirts…So is the fitted(body con) skirt more flattering or the typical flared kind? I see that the Leith brand had the fitted and the flared (the one Cam wore). Just wondering…is one dressier? better for pear shapes?

  2. Yes! Love this! I did not love last year’s version, but I love, love this. The proportions just work so well, and the nod to retro with the Saltwaters is perfect.

  3. Love this look! I have been wearing a Leith Double Layered Tube pencil skirt all the time using your half tuck tee trick. This will allow me to change things up a bit. Question- I do have a small pooch- think the full tuck with a cami will make that more noticeable? Might just have to buy the cami and give it a try!

    And my boys would LOVE this weekend. If only we lived closer. Might need a road trip in the future…

    • It’s tricky! But if you blouse the cami so it falls down over the pooch AND have the pooch encased in a pattern….from the front it looks great. The side view is usually more telling, but that darn side view usually is. 🙂

      • Thanks Shana!!! I’m going to give it a try. And the side view IS more telling, isn’t it?!?! Dang it all- but having kiddos is worth the pooch. (Well, most days it is! 😉 )

  4. REI carries a Toad&Co. skirt called Shirred Thing that isn’t exactly a pencil, but it gives the same look and works well on my 5’2″ self. Also, super cute with rain boots.

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