I Tried: Denim Pencil Skirt



So, okay. Ya’ll.

I tried a denim pencil skirt. Oooooh, did I try.

I was all gung-ho about it before actually wearing one like, “HELLZ yeh, I’ll wear a denim pencil skirt all day erryday”.  I had alllll the ideas for how I’d wear it…all awesome, by the way. Totally.

Note to self: be careful being vocally overconfident about wearing something in particular BEFORE you actually ever try it on when you write for a style blog, because you might just get stuck writing a post about it. ha.

Well, much to my dismay…it’s rather difficult to make a denim pencil work for everyday…when I do not wear heels on a day-to-day basis. I think that with a heel it would have worked out a lot better. However, no heels for me when I’m trying to run around with my three crazies…and besides, I really wanted to try and make the skirt more casual.

Want to see my grand attempts?

Yeh, I knew you would…

Denim Pencil Skirt Take 1.

I saw this pin and it just made sense. Right? I was 100% certain it would look awesome. It had to.





maddie2 (17 of 1)


Well, so it’s not terrible…at certain angles, but then at others it looks a little bleh and frumpy on me. If I had been wearing a pretty strappy heel…yeh, maybe I would have rocked it out a bit more. However, KIDS and no heels, so…it’s not as effortless and cool looking as it is on the girl in the pic, who is so calmly sipping tea on the sidewalk and not pushing a stroller. Darn you, you cool looking tea sipper. I can’t peacefully drink any beverage on a random sidewalk right now, let alone a tea in a dainty mug. haha.


top: Leith Pocket Button-down, from last year – this Marius Stiped Shirt from Revolve looks cool. It could be tucked or even tied in the front? Maybe I should have tried tying mine for a bit more casual of a look…and then it wouldn’t have tucked a bit frumpy-ish.

skirt: Who What Wear Denim Skirt – great skirt. It’s stretchy, so forgiving. It is like any denim skirt though…and it does tend to ride up a bit and have to be adjusted, which is pretty much 80% of my problem with styling one, I think.

sandals: Vince Camuto, from last year – I really am digging their new Adalson Strappy Thong…the Rosey Bronze Leather! It could be interesting with a longer denim skirt…

Denim Pencil Skirt Take 2.

After not loving the skirt with a button-down, I thought I’d take it in a completely different direction: less uptight, more BOHO. How can frayed denim not look good with a peasant-type top? It definitely looked so cool (in my head).





nursing-friendly-outfit-for-summer casual-denim-skirt-outfit

It works. It does, but…it still felt weird. Ya know? Ultimately, I think it came down to my choice in peasant top. I think an off-the-shoulder # would have made this outfit 100x better (I just don’t have one, so I was kind of stuck). I also found myself having to tuck in the shirt constantly and rearrange the skirt back to it’s proper place on my waist. Annoying.  I tried leaving the shirt untucked and…no. It just made it all look frumpty dumpty. grrrr. Again, maybe wearing an off-the-shoulder top (maybe even untucked?) would have solved my problem.


top: consignment find – I really do think a shirt like Madewell’s Folktale or Topshop’s Lace off-the-shoulder top would work a lot better. On that note, Nordstrom has a slew of options in that department.

skirt: Who What Wear Denim Pencil Skirt

sandals: Sam Edeleman Eavan Gladiator– my absolute favorite pair of sandals. They have been worth every penny. Seriously. I wear them with everything.

Denim Pencil Skirt Take 3.

I had a little light bulb go off when I realized, maybeeeee it’s the length that’s throwing me off, so I chopped it…

and added a very slouchy top for good measure, because why not? Can’t lose at this point.




3 (17 of 1)

Yeh. Hmm. Okay. This is a cool look. It definitely edges it all up a bit and rids me of the boring, but…I still can’t seem to figure out if it actually looks good on me. Something’s off. Maybe it’s the ankle strap style of the shoes OR I could have shortened the skirt a bit more. I would then be in that dangerous-let-me-show-everyone-my-hoo-ha-when-I’m-bending-over-to-pick-up-my-kid mini skirt territory though. Ehh. STRUGGLES, people. Real life style struggles.


top: Hatch Longsleeve Tee – great top to throw on any day. It can be worn through pregnancy, postpartum and beyond. One tip, in regards to Hatch clothing: you may have to play around with their sizes. Some of their clothing seems to run large, while others can run a bit small. It also depends on how slouchy you like your look to be. Just something to keep in mind.

skirt: Who What Wear Denim Pencil Skirt, chopped (by me) – will I regret chopping it? Mmm. Not sure.

shoes: Halogen Dylan Espadrille – a really cool espadrille style. I’ve recently been wearing them with destroyed boyfriend jeans or cropped jeans and a black tee. Easy and cool.


SO. After all of that, I got all woe-is-me and whined about my denim skirt issues to the rest of The Mom Edit team.

Laura immediately came to my rescue and sent me this…


Well, OKAY, Laura. Gosh. She seems to nail it.  [NOTE FROM S:  Technically, this isn’t a denim pencil skirt, it’s a denim A-line skirt.  Totally different.]

On Laura:

topJ. Crew Stripe Tee (similar) – she also suggests this ASOS Swing Vest, because, I quote, “LOVE LOVE!”

skirtGAP denim Trapunto Skirt (similar)

shoes: Sam Edelman Petty – she also suggests these Matisse Nugent

Maybe a denim skirt is not my thing or maybe I am just wearing the wrong style…

Other Denim Skirts to Consider


Although, I am now definitely curious as to how an off-the-shoulder top would look with my chopped skirt. hmmm.


Have you worn a denim skirt? Do you wear it better? Do you know the magic trick to making it wearable and look awesome? Does pencil vs A-line make a difference?  Please do share, lovies…

It’s for my emotional well-being.