Making Pencil Skirts Casual for the Weekend: Three Key Things to Know

Casual Clothes · You Pick Wednesday

You probably have at least one in your closet. A pencil skirt. An business office wardrobe staple for many of us. And they might get a lot of wear, too. I mean, we are at work more than we’re at home. Or, at least, it seems like that for me. But who wants to have two entirely separate wardrobes? One for work and one for play. I mean, that gets expensive! Which is why faithful reader Kelsey asked me how should could make her pencil skirts casual for the weekend.

Pencil Skirts Casual Outfits

Clockwise from top left

Shout Out to You | Merrick’s Art | | Gap | Atlantic-Pacific | Fashion on the Fly | J. Crew | Refinery29

I collated 8 different casual pencil skirt looks that include what I consider to be the staple pieces in making your pencil skirts casual.

1. A loose-fitting, casual shirt.  Plain, patterned, striped, graphic, whatever. It needs to be casual and not super-tight.  T-shirts, sweatshirts or tank tops will all work for this purpose as long as they are loose and comfy.

2. Flat shoes. Sneakers are a great way to dress down your skirt but if you think that’s TOO casual then just flat sandals are a good way to go in the summer.

3. Casual outerwear. For work we tend to pair our pencil skirts with cardigans or blazers. For the weekend, though, jean jackets, utility jackets, or zip-up sweatshirts are the key making those pencil skirts casual.

So, what do you think? Would you wear any of these outfits?

Don’t forget you can always submit your own You Pick Wednesday questions via Twitter, Facebook or email!


13 replies on “Making Pencil Skirts Casual for the Weekend: Three Key Things to Know

  1. Sabrina Domingues

    Love the stretchy ones! I am trying to lose pregnancy weight and the stretchy ones have enough room for my hips. I don’t need to get rid of them right away after I shed some pounds 🙂

  2. kelsey

    THANK YOU! I love this! I have so many pencil skirts and I’m always sad I can never wear them anywhere other than the office….until now! I really love the look with the military jacket and chucks!

  3. Anne

    These are all really cute, especially the outfit with the striped tee and denim jacket. But I just can’t see a pencil skirt as casual wear! Maybe I’ll give it a try with my green pencil skirt, since it seems less businessy than my black or gray ones.

  4. Katie of Alaskan Weredork

    *sigh* i’m going to have to raise my hand to the having two separate wardrobes. My jobs are really active and physically demanding so I usually wear cute jeans and a modest top. I usually change when I get home because it’s more fun to run errands and do housework in something that’s not sweaty and dirty. (So I guess this sort of doesn’t apply to me, no pencil skirts at work for me. But it gives me some ideas on trying to mesh my two wardrobes together a little bit.) I totally think flats are adorable with a pencil skirt btw.

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