Would You Wear It: Denim Skirt

Would You Wear It: Denim Skirt

Welcome to the weekend and another edition of would you wear it. Each Saturday my friend Pam and I share a mannequin we’ve seen and ask our readers if they would wear what she’s wearing. We do this to foster conversation and understand what style and fashions work for you.

Please keep your comments personal and related to why this outfit would or would not work for your shape, coloring or lifestyle.

Pam and I don’t share our opinion of the looks, however, she has begun to share her thoughts in a subsequent post. Is this something you’d like to hear from me?

Denim skirts come in and out of fashion often. They’re back this spring in many shapes and washes.

So tell me, ladies, would you wear this?

Why or why not?


Here are the weekend sale updates:

Loft – 40% off your entire purchase with the code LOVEMOM

NYDJ – 30% off sitewide

Talbots – 30% off all tops with the code TOPS

Chico’s – 40% off your purchase with the code 50849

Spring Jackets 

Soft Surroundings – 10% off with the code MOMS19

Now let’s go see what Pam’s Mannequin is wearing here.


Thanks for reading and have a great day.

Affiliate links within this post may generate income for AWSL at no additional cost to you. When you shop through my links I earn a small commission which helps support my business.
Affiliate links within this post may generate income for AWSL at no additional cost to you. When you shop through my links, I earn a small commission which helps support my business.


  1. May 11, 2019 / 3:39 am

    Yes, I would wear a denim skirt…but not with that top. The top is the wrong fit and style for me. Happy Mother’s Day Jennifer!

  2. Cindy
    May 11, 2019 / 3:43 am

    Yes, I would wear the denim skirt. I like the length & the wash.
    I’d be very interested to hear your take on the Would You Wear It items.

  3. Penelope
    May 11, 2019 / 4:13 am

    Denim is very practical and versatile Each brand fits differently so defiantly have to try on. I like the buttons down the front on the display skirt but the sweater does nothing special for the outfit. The trim style of the skirt would be ok on my figure type if the fit is correct. The length would probably be too long as I am petite. That is one problem with denim.. it’s not easy to alter.
    But I always have a denim skirt in my closet. I think they are a wardrobe staple.

  4. Judy Casingal
    May 11, 2019 / 4:14 am

    Love the color of the yellow dress, but would never wear horizontal stripes or that type of knit. It would show every lump and bump my body has. Happy Mother’s Day!!

  5. Chris
    May 11, 2019 / 4:22 am

    I LOVE denim skirts and have held on to almost all of mine through the years. I think they are as classic as a Chanel jacket. With the right top, jacket, and accessories a denim skirt can cover most all occasions. Happy to see they have cycled back around,

  6. Yvonne
    May 11, 2019 / 4:25 am

    I might wear a denim skirt again if it was white denim. I’m not a fan of blue denim for myself anymore. I’ve only owned 3 denim skirts in my life. The first in the 70’s when we made them from an old pair of blue jeans. Anyone else remember doing that?

    • Laurie
      May 11, 2019 / 3:35 pm

      Yes, I made a denim skirt out of old jeans in the 70s! Thanks for the memory!L

  7. Eileen
    May 11, 2019 / 4:28 am

    No, as a pear they never fit right, and the buttons down the from would open up when I sit.

  8. Sheila Porter
    May 11, 2019 / 4:36 am

    Just bought a demon skirt from LKBean. But don’t like this one w the buttons. Doesn’t look smooth when sitting, etc. And I like a darker (slimmer) denim versus washed. But I’m 5’ tall, so…

  9. Nancy Hopkins
    May 11, 2019 / 4:40 am

    Love denim skirts. When I was teaching, I wore them often. This one looks comfortable.

  10. Mary
    May 11, 2019 / 5:07 am

    No. I had a similar one years ago. No need to redo. I would wear the sweater.

  11. Wendy Dunbar
    May 11, 2019 / 5:14 am

    Yes, would love to hear your comments about the outfits you post, like Pam does it, ‘after the fact’. I find the WYWI very educational! As for me personally, this is a cute look but would not work on my (large) pear shape. I had a skirt very similar to this in the 70’s as well. I noticed on the mannequin it hits her at her narrowest point on leg, which is good! I might consider a fuller or Aline denim skirt, or maybe wide cropped-leg denims for a ‘skirt’ look. Sweater is cute but agree with someone else who said ‘not with this skirt’.

  12. Angie
    May 11, 2019 / 5:17 am

    Been there done that!

  13. Sandy
    May 11, 2019 / 5:19 am

    I like the look of a denim skirt, but not how it feels and moves on me. I had one and ended up donating it. It wasn’t comfortable. They are tight around the waist, no “give” when I sit down. If I saw it on you, I’d love it, but not for ME to wear it. I love the sweater that it’s paired with. Being rather busty, I like tops that don’t button and gap open in the front. I really like the sweater dress, but I can’t wear them. I’m short and they are usually too long on me and I can’t hem them. I would LOVE hearing opinions from both you and Pam on the looks.

  14. May 11, 2019 / 5:22 am

    Yes to the denim skirt outfit. I could use that now…with our foolish spring then trade the white sweater for a pretty tee and necklace as it warms a bit.
    On the yellow dress? No, I’m too lumpy, bumpy for that. Even with Spanx!

  15. May 11, 2019 / 5:25 am

    In my previous comment, it should be “cool ish” spring not foolish. I rewrote the word three times?

  16. Laurel
    May 11, 2019 / 5:26 am

    I finally learned, after several attempts at denim and white denim skirts, to stop buying them. I love the look, but the fabric is generally either heavy and unflattering, or stretchy and unflattering. Sad to say, I’ve given up. I think they remind of the denim skirts I wore when I was younger and loved. But alas, my body no longer looks the best in them.

  17. Merri
    May 11, 2019 / 5:26 am

    Yes I would wear a denim skirt and love to in the summer with fun colour T-shirts. I have a white one I wear a lot when the weather is warm and am looking for a red one!

  18. May 11, 2019 / 5:34 am

    No I would not wear this skirt. I am so broad in the hips and have skinny legs, so a skirt on me looks really weird. I end up looking even broader! Plus, I never wear horizontal stripes, which are both present in the dress and the sweater.

  19. Marty K
    May 11, 2019 / 5:37 am

    No to all! Don’t wear dresses, and certainly not in yellow striped knit fabric or sleeveless. The sweater on the left would wash me out and is too short. No denim skirts for me either as I would prefer denim crops in a darker hue

  20. Ellen
    May 11, 2019 / 5:47 am

    Love the denim skirt, but it would probably go the way of all my denim skirts past and present, moved about from one closet to another in my house each season, rarely to be worn. Think it has to do with one commenter’s remark: they’re just not very comfortable. Hate the sweater they’ve put it with, and think I would hate it under any circumstances.
    That dress? Either it would show abundant forensic evidence of every mindless sleeve of Thin Mints I’ve consumed in a single sitting, or if you were a person who carefully cuts Thin Mints into quarters before licking the crumbs off fingers and throwing the rest away before frantically doing 42 sit ups, it would show every knob of every bone in your body.

    • Linnie Z
      May 11, 2019 / 1:10 pm

      Haha! Now THAT is funny! Knobs, SMH, still laughing.

  21. Beth M.
    May 11, 2019 / 5:50 am

    I might wear this skirt and sweater, but I’d have to add something to the mix, like a scarf or a long necklace, because it looks very dull as is. I have several denim skirts and wear them year-round in Florida. They seem slightly dressier than shorts and are a nice basic that go with everything. I’m not thrilled with the pale wash, however.

    And yes, Jennifer, I’d love to hear your takes on these outfits!

  22. Deborah Broughton
    May 11, 2019 / 6:01 am

    I bought a pair of denim …i can’t think of the proper name but like a gaucho ? Senior moments this morning. But anyway I ended up loving them and wore them often last summer. The fabric was a light weight stretch denim.However, I don’t think I would like this skirt , it looks uncomfortable and that top looks odd with it.

  23. J Johnson
    May 11, 2019 / 6:06 am

    The high waist is a plus but it appears there is no vent or pleat in the back of this tapered skirt, which would make walking difficult. I also don’t care for denim that is faded out in the thigh area. So this would be a “no” for me. Even in a skirt, denim is hot where I live in south Texas. And definitely “no” on a body conscious ribbed yellow dress. Those days are long gone. I would be interested in your opinion on how to work with the items you show in WYWI!

  24. Betty (SC)
    May 11, 2019 / 6:30 am

    Yes, I’ve been a fan of denim skirts for a long time! This is something that can be dresed up with cute sandals & blazer, or very cute casual with a striped tee and sneaks! But the white sweater shown on the mannequin isn’t very interesting or sensible looking- looks too tight fitting and does nothing to add to the denim skirt. Buy the skirt and jazz it up.😊

  25. Lisa Cobb
    May 11, 2019 / 6:31 am

    I love the denim skirt and white sweater! Its just so classic and I live in MA where spring is still chilly. I have to pass on the dress. It seems like it would show every lump and bump.

    • Lea
      May 12, 2019 / 7:56 am

      I agree!

  26. Cindy
    May 11, 2019 / 6:40 am

    I like denim skirts. I agree that the buttons on this one may be problematic. I also like the top. I just don’t like them together. The effect looks sloppy.

  27. RoseAG
    May 11, 2019 / 6:45 am

    Love denim skirts but not this one.
    I’m too curvy, and the buttons will pull across the hips . I do have a skirt this style, it’s gray denim and I really wanted that color, but I have got the spaces between the buttons safety pinned together so they don’t gap. There are lots of blue denim choices on the market today so I’d keep shopping for one with a kick pleat and the usual zipper front.

    They’re definitely a workhorse in my wardrobe.

  28. Phyllis
    May 11, 2019 / 6:57 am

    I like the denim skirt and sweater. The sweater is a good length for me, but I would have to try it on to see what those stripes would look like on my full bust. Since it is cream on cream, it might work. It needs a necklace or a long scarf to add some punch. Denim skirts are a classic. Now the yellow dress is a big NO. I don’t like the color. You have to be very thin, in my opinion, to get away with those stripes in a bright color. Definitely no to the clingy, body conscious style.

  29. May 11, 2019 / 7:02 am

    I would love to wear that skirt, but probably couldn’t do it. In order to get it around my large waist, it would be falling off my hips. This is my usual problem….

  30. Rose Brock
    May 11, 2019 / 7:10 am

    I like the denim outfit. I have similar denim skirts. Will have to get them out again. Hope they still fit! Happy Mother’s day Jennifer!

  31. Glenda
    May 11, 2019 / 7:11 am

    I’m a “maybe” on the skirt: not opposed to it, but I’d like to see it on my menopausal shape before committing. I’m sure I’d choose a different top with it. No to the yellow clingy dress unless I had some dump-truck strong Spanx and a linen blazer over it! 🙄

  32. Linda
    May 11, 2019 / 7:26 am

    I wouldn’t wear the skirt bc I just don’t wear dresses or skirts that often. The sweater would probably be okay—would have to try it on; necklace required. The yellow dress is a big no: wrong color, shape, and fabric.

  33. Roxanne
    May 11, 2019 / 7:53 am

    No, I would not wear it. Personally, I think denim skirts look tired and matronly no matter what the wash or cut… or age of the wearer. It’s what Clinton Kelly used to call the “I Give Up” look. I love the sweater, although I would need it in another color so as not to wash me out.

  34. Lori Stewart
    May 11, 2019 / 8:03 am

    I love denim skirts and would happily wear this one. I have worn them since my high school days in different iterations. I will wear them forever. I like the button detail in this one and the length is perfect.

  35. Lily
    May 11, 2019 / 9:24 am

    When I was on vacation I saw a woman wearing a denim skirt and sweater. She looked casual, comfortable and very put together. What she did differently – the skirt was colored denim, no buttons, shorter, the sweater over-sized, neutral color, natural fiber with a loose weave. She styled the clothes with subtle metallic Birkenstocks. I don’t normally wear skirts, but that woman changed my mind. So, yes to a denim skirt, but no to the proportions as shown here.

  36. Cindi
    May 11, 2019 / 9:26 am

    Yes, I would wear it. I love my denim skirts in different styles and colors. The sweater would work for me, especially when the weather is cooler. For those worried about the buttons gapping. You might need to size up. That’s what I have found with button down blouses. I also like the dress pictured here. I find stripes with the right fit to be flattering.

  37. Donna Doyle
    May 11, 2019 / 9:49 am

    I would wear the denim skirt, when you aren’t sure what to wear they usually will fit in anywhere. I wouldn’t wear it with the sweater however. I would love to hear your take on the outfits.

  38. May 11, 2019 / 9:54 am

    If I wore skirts, I would wear this denim skirt. I prefer skirts without any embellishments, but the buttons are OK if they are functioning. I would not wear it with that sweater top. The yellow striped dress is cute but only if the wearer thin and slim.

  39. Suzi
    May 11, 2019 / 10:16 am

    Would love to hear your opinion on the outfits. Your ability to pick out what is and isn’t working is very helpful.

  40. Becky
    May 11, 2019 / 10:52 am

    I like denim skirts, but this one would not be flattering for me. The length is a bit awkward for my short legs & the slim button front style wouldn’t fit my proportions.

  41. J'Laine Bradley
    May 11, 2019 / 11:05 am

    I just took one exactly like it to the Goodwill because I couldn’t figure out how to style it. I just didn’t think it looked good on me.

  42. Katrina
    May 11, 2019 / 11:20 am

    Yay on the denim skirt!! I wear one all year round. Great with tights & boots in winter. Great with cute sneaks & T’s in summer. But I’ve discovered that if the skirt is woven, the top should be, too. Same with knit skirt – a knit top works well. That’s why this dull sweater looks “off” with the woven denim skirt. Now put in a bright or white woven shirt with a fun scarf or jewelry & it will snap!! My rule of thumb.😃

  43. beth byrd
    May 11, 2019 / 11:45 am

    I like this skirt and would definitely wear it. I don’t think the sweater goes with it at all — it’s not the right fit and the color is too blah with the light denim.

    I think this skirt would look great with a striped tee and a short jacket. It’s really cute but that sweater doesn’t do it justice.

  44. Peggy
    May 11, 2019 / 12:05 pm

    I don’t wear skirts, dresses, or stripes but I like the two mannequins, but not for me.

  45. Kay
    May 11, 2019 / 2:20 pm

    No, I think not. I always found denim to be a bit too heavy for me (in a skirt.) I also do not like the slim pencil cut silhouette in this version.

  46. Mary Lou
    May 11, 2019 / 3:22 pm

    I don’t wear skirts and don’t like this color or the buttons up the front. I’d love to know your opinion and the reason for it.

  47. Cimmie S
    May 11, 2019 / 3:28 pm

    Was wearing a denim skirt similar to photo when I read your piece. Like many of above comments I too regard a d/skirt as a classic & usually have one in my wardrobe. But, I think the white top doesn’t work with the skirt as displayed. Think it has to do with the style of top itself as a white or pale blue shirt always looks crisp with a d/skirt.

  48. Lesley
    May 11, 2019 / 4:31 pm

    The yellow dress is a definite “no! no!”. I’m the same figure type as you Jennifer – broad shoulders then more or straight down from the shoulders. My bust, waist and hip measurements each approx 39 inches with rippley bumps in between! The denim skirt I would wear and the jersey shape would work but outfit needs a statement scarf to cheer up the look.

  49. May 11, 2019 / 5:36 pm

    Yes, I would wear both! After 5 years of effort, I am a size 6 or 8 and I definitely can fit in them. I love warm yellows and stripes, so the dress calls to me. I would add a jacket to give it more pop. Flame red or turquoise would really liven it up.
    I also like the denium skirt, I hope it has pockets. The sweater is a nice neutral color, but might be too warm for the Gulf Coast, so I might try to find something similar in a lighter weight. Or belt a darker denium shirt over a bright red tank.

  50. Donna
    May 11, 2019 / 10:32 pm

    Yes to the skirt. That length is hard to find in denim and vertical buttons are slimming. I find denim easy to wear in summer…cooler than shorts, casual,neutral in color, so mixes with almost anything…hides underwear lines! The sweater is cute but bland, so red purse, earrings or sandals would liven it up. Generally, I wear colorful tops with that kind of wash. It’s a classic.
    And yes, would love to know your take on these outfits.

  51. Lynn
    May 12, 2019 / 6:18 am

    Both outfits appear too dirty to me. I guess I like clear, clean colours. As for style of the skirt, buttons over the tummy area are a no-no for a certain age or shape group. Length is nice on the skirt. The dress has perfect arm cutouts but that us all I can say about a clingy dress with horizontal stripes. Two thumbs down this week.

  52. Janet
    May 12, 2019 / 8:19 am

    I wouldn’t wear these looks because they just don’t excite me…or at least interest me. At this point in my life I’ve got most of what I want or need so I need to be a little inspired to buy something. As for you adding your own comments I would say do whatever you like but it isn’t necessary for me. I just like everyone speaking for themselves and the post not turning into a debate. After all, there is really no right or wrong here, just whatever works for each of us. I do enjoy reading everyone’s comments.

  53. May 13, 2019 / 7:37 am

    I personally wouldn’t my legs are not good enough to wear this length nor is it a flattering shape for my body type!

  54. Susan Bradshaw
    May 13, 2019 / 12:43 pm

    I would not wear this one — I think a denim skirt should either be long or short, not in between; and I don’t like the buttons in the front. Prefer a zipper.

  55. Cyndi
    May 13, 2019 / 5:17 pm

    I would wear (not with that top) I vote yes for a follow-up post from you!

  56. Brookie
    May 14, 2019 / 12:13 pm

    NO, I hate skirts of every type. I am short 5’1″ and feel they cut me in half and make me look even shorter. Also I find Denim is so pedestrian, it’s a work around the yard item in my mind.

  57. penny luckenbaugh
    May 15, 2019 / 3:25 pm

    I love the denim skirt. It looks practical and comfortable. I am on a serious search for one in PDX- so far no luck. I got the Coldwater Creek catalog today- the denim skirt was tiered and maybe cute on a twenty-something, but other wise too costumey.

  58. Georgina
    May 20, 2019 / 3:11 pm

    A denim skirt is not easy to style and l think is best left to a mini length on female under 30. Maybe because the skirt is styled on a mannequin it just looks boring with an equally boring jumper. Perhaps styled with bottom button open, a coloured/gingham shirt with the sleeves rolled up, top button open and tucked in with a leather belt and espadrilles. Just my thoughts, as l said ‘not easy to style’

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