Pencil skirts, especially wool ones dress up an outfit to make it look more formal. Since I don’t need to be so fancy, I have to make it work for casual situations to fit with my current lifestyle.
Instead of putting away all the “dressy” clothes, I’d much rather find different ways to wear them.

With many closet staples, they can be worn a multitude of ways but some are easier to remix than others. When it comes to basics, I tend to think of the most traditional way it’s worn. Not sure why, but those images always comes first when putting outfits together.
I recently had an “Ah-ha!” styling moment with blazers, so it’s about time to extend the creativity to the pencil skirt.

A simple tee, a casual jacket, and neutral heels make a great pairing for the wool skirt. You can wear a denim jacket, a wrap cardigan, or a fitted hoodie to garner the same effect.
Swap in flats or oxfords. Change the tee to a printed blouse. Mix and match everything and anything! The more you experiment, the more outfits you discover and the easier it becomes to put great looks together.

Outfit Details: Madewell jacket – XS, Urban Outfitters tee- XS, Paul et Duffier skirt – 2, Aldo pumps
Shop: jacket, tee, pumps
By the way, sign up for the Petite Fashion Challenge #6! The deadline is Thursday 5PM PST and make sure the PFC button works (re-insert the double apostrophes and the code should work properly.) Email me if you have any problems.
For the non-bloggers who want to participate, email me your outfit photo and description and I’ll post it along with mine. FYI, we’re 5 people away from hitting 50 participants! EXCITING!!

{ 13 comments… read them below or add one }
Hey great idea! I always feel too dressed up sometimes at work with my pencil skirts on.
Just an aside, there is code at the top of your header that I’m thinking isn’t supposed to be there?
I never really cared for pencil skirts but you, Kendi, and some other bloggers are making me think otherwise. I would have never thought of wearing it with that jacket but it looks great!
I love that Madewell jacket! And the pencil skirt looks lovely and comfortable on you!
All great tips, Jess! All the pieces you’ve mentioned are ones I own, so I’ll be trying them out together. I’m thinking pencil skirts that aren’t tailored to fit me perfectly would be a great experiment for the casual look… or maybe I’m just trying to think up reasons not to return the ones that don’t fit me perfectly
I love the colors in your outfit, so cute!
@Curls and Pearls: For me, I think of dressier outfits easier than casual ones. But when there’s people wearing sneakers around…I have to take it down a notch. Btw, I’ll fix that code thing. Thanks for the heads up.
@Simple Subtle Style: I’ve picked up several pencil skirts but I don’t wear them as much as the other skirts, but I hate to see it collect dust. So I had to find a way to make it more accessible for everyday wear.
@Feather Factor: Thanks! The Madewell jacket is one of my faves.
@Cee: I’ve been doing the same thing, when it doesn’t fit perfectly and I don’t want to get it tailored, I just find other ways to wear it so it doesn’t sit around. =)
@Callandra: Thanks! I just pulled the colors from the printed tee to make it all blend together.
I also always feel a bit self-conscious when I try to wear pencil skirts out to casual events. You make it look effortless and breezy and casual – love!
i love the simple tee and flowy jacket you added to the pencil skirt. it does tone it down a bit while still looking chic and stylish!
I’ve always told myself that I could wear pencil skirts casually, but I have to admit that I don’t reach for them very much and usually opt for well, casual skirts on weekends. Thanks for reminding me to wear them!
I love the color of that skirt! So pretty
@Larie: I felt the same way too, so I had to find a way to incorporate it better without it being too noticeable.
@Kileen: Thanks! That’s exactly what I was hoping to achieve.
@PetiteXXS: I don’t have too many skirts to divide it up, so want to wear them all more often. =)
@Really Petite: Thanks! I think the aged look of the skirt makes it more subtle.
I have the same philopshy, I don’t save “dressy” clothes for specific occasions but mix and match them with other pieces so I get more wear out of them.
Exactly! Items that do double duty are way more practical for my lifestyle. =)