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.




  1. Great, honest post. I love denim skirts, but have realized that the pencil skirt struggle isn’t worth it. The constant adjusting, as mentioned. And the lack of movement when chasing a small ball of child energy. A button front A-line is so much more workable, and flattering, with both heels and flats. And off shoulder tops. And tees, half-tucked. Love the hacked off look, though!

  2. I think it all depends on (a) body type and (b) proper fit! I LOVE my new J. Crew denim skirt (pencil with frayed edge). I sized down (from my usual 29 to a 27) because I like to wear my denim skirts high on my waist. I don’t have much in the way of curves and, for me at least, wearing a denim skirt as a high waist kind of fakes a waist? Or something? If I wear the size I would take in jeans, that is when I am constantly battling with the waist and yanking it up down and all around. I’m actually wearing it today! I don’t know how to add a pic but I paired mine with a flowy white tee, with an unbuttoned long button down (actually a j crew swimsuit cover up) and a pair of flip flops. But I live in a beach town where flip flops are always the right shoe. 😉

  3. I must second the notion that a denim pencil skirt is only a good idea in theory. In practice, we wear denim skirts when we are out doing sweet stuff and it’s too constricting to bend, sit, chase all day. Also, mine always got twisted to the side if I had to walk anywhere. I had more success with a denim A-line with snaps up the front. Open a few snaps at the bottom and you have a slit. Mine was dark denim so it was a more polished vibe. I liked it with a crisp t shirt, tucked or untucked if it was short. With an easy heel, like a platform sandal. Needed more substance on the bottom.

  4. I like this post. I think I learn more when The Mom Edit posts about what doesn’t work vs what does work. Not to mention it mimics my life more because I only keep about 10% of what I try on. Let’s face it, most stuff doesn’t work.

    I didn’t think these looks were terrible looking, but I didn’t like them because all I kept thinking about was how uncomfortable it looked. Like your legs were in a denim straight jacket. I like a good pencil skirt, just not around my kids.

    And I’d just like to vent about something kind of off topic for a moment – to all moms who wear skirts to any kid event that involves sitting in a circle with other adults, yes, whoever is sitting across from you can see straight up to your hoo-ha, so either cover that up, or better yet, wear more interesting underwear. Thank you.

      • Yes, a pink leopard print would brighten my day a whole lot more than boring white cotton! Hehehe. If you’re going to flash me, at least do it in style!

  5. I’ve never liked pencil skirts because I find them totally impractical for the way I live. They restrict movement to a Mad Men era wiggle and I ain’t got time for that. Whoever came up with the idea of making an already restrictive skirt out of denim is, as Dar Williams would say, “No friend of mine.”

  6. Glad I’m not the only one who feels that way about pencil skirts. Like the theory but not the reality. That said, I have a white denim slight A-line that I could easily wear multiple times a week.

    P.s. I also enjoy your opinion on what DOESNT work.

  7. Finally gave my denim pencil skirt to the goodwill last week. I realized it had sat unworn for a year at least. The few times I wore it to work (teacher) I felt so restricted. I also thought it made me look quite frumpy and like I had a gut. I don’t have a gut- I do have fat thighs, and I though it was quite flattering from the back, so I bought it. In the end, I found that I like to be both more comfortable and to NOT look like I have a gut, even if it did look good on the bum.

  8. I wear BLANK NYC denim skirts instead of shorts – almost every day in warm weather. They are a good length, stretchy, and have cool details — frayed hems, destroyed or acid wash. I have six of them — six!! I think two things — has to fit (the fit on yours is too frump for your tall-drink-of-water bod) and don’t overthink styling. Love that you showed us what doesn’t work!

  9. Love the chopped look. I think A line skirts are totally doable with kids. Mine doesn’t have to be adjusted because there’s extra room around the booty and hip area. I feel with pencil skirts they’re so dang tight when you move you always have to adjust it afterwards. And lastly I think the last outfit is the best! Great honest post!

  10. You have inspired me to drag mine out from the back of the closet soon. At the least I have one white and one, possibly two, traditional blue. But it has been years since they have seen the light of day. I also think denim is difficult in warmer climates because one it is warm enough to go bare legged, it is too warm for denim. I do prefer the pencil cut, as a-line skirts look like giant bells on my scrawny legs.

  11. I *just* attempted the pencil denim skirt last week. I had grand plans in my head of how cute it would look. I put on my outfit. Nope. Even my husband was like “really?!?” So tried a different top, different shoes, added a belt, tried a cardigan. Finally, the pencil skirt went in the donate pile. I just couldn’t get it to look effortless chic, and every time I moved I had to readjust!!! I do think it’s cute when I see it styled in an ad, but my reality doesn’t fit that styled moment in time.

  12. I also like seeing the attempts that didn’t work. Also agree that the pencil skirt did look uncomfortable which might have been part of the problem.

    That said, I’m anxiously awaiting the dress post that is nursing friendly you mentioned on IG since I had a baby one month after you and am nursing like crazy, also with a toddler leaning on me. I currently am ok on bottoms, but anything you have for tops to nurse in would really, really, really help!

    My first only took a bottle and dealing with a pump and shirt is apparently a whole different ball game than baby and shirt especially with toddler accoutrements…

  13. I bought a totally basic very light weight very stretchy denim pencil skirt in 2010- not at all “in” then I believe. It has served me well- I think because it is not stiff at all- it was perfect for a dress down Friday. I am planning on wearing it this summer with off the shoulder tops.

  14. I’ve been wearing my denim pencil skirt (which is almost identical to yours before you chopped it) a ton! I find it to be super comfy because it’s not too tight. My favorite combo so far is a slouchy graphic tee with my trusty Converse. I also tried it with a button up shirt, like you did, but I actually did wear strapped heels (church) and it totally worked. I think next I’ll try a graphic tank knotted at the waist and my gold Birks. I love your third combo!

  15. Take 2, last photo = my reality!! I don’t know how we survive the physical combat that is nursing/toddler attack. 😉

  16. I had a love affair with pencil skirts that abruptly ended with the birth of my first–just not flattering on a post-partum bod. I think the problem is with the skirt, maybe if it had more of a tulip shape? So it nipped in at the bum and then kicked out at the knee. Also, you may want to pull skirt higher on waist…? You are brave and look terrific regardless. I don’t recommend attempting the pencil until youngest’s first bday.

  17. Oh my gosh- such a validating post! I seriously just two days ago tossed both my pencil and shorter denim skirts in the donate bag. And I’ve had them quite a while, also WILLING them to work! One was even frayed a bit too, which felt like “how can it NOT work?” But they were always the thing I put on while getting ready and ultimately changed out of before leaving the house because they just never worked. It didn’t make sense to me how these cool skirts were so frumpy ON… but they were. SIGH. I actually never even wore them. And I’m a budget clothes person so they really have left me scarred! LOL

  18. Well, I don’t own a denim pencil skirt but my trusty black J.Crew pencil skirt is one of my favorites for work (or used to be- I’m currently 8 months pregnant). My favorite way to wear it is with a simple v-neck t-shirt and an interesting necklace. It’s definitely best with heels, but still good with sandals. I think the trick is something slightly fitted on top- button downs (peasant tops, etc.) always billow out and look weird, in my opinion. I love seeing your efforts, though!!

  19. I have the same struggle with denim skirts. I love them in theory and had a lovely comfy one that always felt like I was dressing for a modest-clothing blog, and not in a good way. I think denim-style pockets without the separation between the legs that comes with actual jeans? Makes for a wide-looking surface (I have some curve in my bum and hips, which contributes, I’m sure!).

    Also wanted to suggest – for you and readers who like the shape and style of the Hatch shirt? — $20 per shirt (ish) and bamboo and so soft. I have 3 l/s ones, two s/s ones (wearing a roll-sleeve s/s now) and ALL the colors. Same idea – big torso and small sleeves. I think the top and tunic could both work well through pregnancy and postpartum (I’m 11mo pp myself, which was part of the appeal) for many women. I’m 5’3 130 and take a small (S,M,L) and also do the front tuck for perspective to make it more flattering unless I’m wearing leggings. The regular top covers enough for casual errands/home leggings. I haven’t tried the tunic yet because really long tops make me feel too short (I have short legs and a long torso).

  20. I don’t own a denim pencil skirt, but love the idea. I wore a ‘made by me’ black stretchy pencil skirt with a striped button down tied at the waist and sleeves rolled up with saltwaters yesterday and looked/felt great. I think your tip about tying the shirt at the waist in pic #1 is spot on. Pencil skirts that look perfect (taper at the knees) definitely limit mobility. Luckily my kids weren’t with me for the errands. Once home again I found myself pulling it up constantly to allow myself more room to walk.

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