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Denim Skirts for Women Over 50: How to Style

Denim skirts are a fashion trend that hasn’t graced the front of fashion magazines since the early 2000s. Lately, I have seen them absolutely everywhere! Whether you love them or hate them, it appears this fun alternative to jeans is here to stay for a while. I think they are the perfect mix of casual and dressy, and I’m having so much fun trying out different styles and lengths in my closet. Today, I’m sharing a few denim skirts I’m loving for women over 50 and some ideas on how to style them.

Denim Skirts for Women Over 50: How to Style

You’ll notice that I’m wearing the same outfit in most of these skirt photos. I wanted to show you how big of an impact the length of the skirt makes on the overall look. You’ll have to let me know in the comments which length is your favorite!

First, let’s talk about my thought process when styling a denim skirt for women over 50 and what items I paired with the skirts. I started the outfit with a white square neck sleeveless tank top bodysuit. It has a slight ribbed texture and a very subtle compression. I know you gurls are thinking, “bodysuit? NO WAY!” but trust me. It has snaps for easy restroom breaks and looks much cleaner than a shirt that keeps coming untucked. This will be great for layering under sweaters, shackets, denim jackets, and more this fall and winter. I layered over the bodysuit with a cozy crewneck cardigan from J.Jill. Cardigans are perfect for transitioning from summer into fall because you can take them off if you get too toasty.

I love this classic black crossbody from AllSaints. It’s so chic, and it goes with absolutely everything. Plus, it has the perfect amount of room for all the essentials I bring with me daily, like my phone, wallet, keys, and lipstick. The crossbody looks so good paired with these black d’Orsay ballet flats, which are so cute and affordable at under $25. Flats are a great transition shoe as we head out of sandal season and into closed toe shoe season.

#1 Loft High Waist Denim Midi Skirt

First up, we have this midi denim skirt from Loft. This is technically a petite skirt, but I’m 5’6″, and I think the length worked fine on me as it hit at mid-calf like the website says it should. It has a button-closure fly and a small slit right up the middle that came right above my knee. I wanted to add a little extra definition to my waist, so I used one of my favorite belts. The belt comes in four other great colors, but you can never go wrong with a classic black!

This skirt would look equally as cute with a tee shirt, blouse, or sweater. One styling tip for putting together an outfit with denim skirts is to tuck your shirt or sweater or choose a fitted top. This helps to ensure you don’t look frumpy or shapeless.

#2 Gap Denim Maxi Skirt

Next up, I tried out a maxi length denim skirt from Gap. I think this would be an excellent option for chilly fall and winter days and nights, as it provides the most leg coverage. The combination of the super high waist and the asymmetrical seam make a very flattering silhouette. I love the fun raw hem at the bottom and the darker wash. It does run a little big, so consider sizing down when ordering.

I like the combination of the ballet flats with the denim skirts, but I’m curious to see how this maxi skirt looks with other fall shoe options like boots or booties. What shoes would you pair with this skirt?

#3 NYDJ High Waist Denim Skirt

If I had to choose one length of denim skirt, I would choose a knee length one as it’s the most versatile. It would be so easy to dress up or down, and you could wear it in any season. Style it with a tee shirt and white sneakers now; a tank layered with a cardigan and booties throughout the fall, and a sweater with knee high boots in the winter.

This denim skirt is unfortunately almost completely sold out, but don’t worry. I’m sharing another fabulous knee length one next.

#4 Talbots Denim A-Line Skirt

If you’re looking for a knee-length denim skirt, this A-line skirt from Talbots is a great option! I ordered in my regular size 10 but needed an 8, so be sure to size down accordingly. If you’re worried that the midi and maxi skirts look matronly and frumpy, you’ll love that this one hits right above the knee, which keeps you looking age-appropriate and hip.

I styled this one a little differently than the other outfits, starting with this navy layering tank. I’ve been wearing it by itself while the weather is warm, but it will make a great base layer when chilly temperatures arrive.

When researching for a recent post about how to style sage green, I found this gorgeous and inexpensive sage cardigan. I love the combination of the navy with sage! It comes in over 20 colors if you’re looking for a cardigan in a different color.

I switched out the black bag for this Italian Leather Triple Compartment Crossbody that I’ve been carrying a lot over the past few weeks. I love the size. It has three separate compartments so I can keep so many things in it. The bag is a great size and seems to hold up to my rough ways of dealing with handbags. It goes with everything, including these suede d’Orsay flats.

Which denim skirt was your favorite? Let me know in the comments!

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  1. Sandra Myers says:

    I just received my white and blue denim midi skirts from JC Penney great deals, great quality as well. I am going to pair them with white crisp tees, navy leather ballet shoes or a soft blue jean wedge. Very cute. These ladies look great!

  2. Susan Wiley Grim says:

    Love the options with a denim skirt, cute with boots, cute with Sperry’s. Thanks for reminding everyone.
    Susan Wiley -Grim

  3. Joyce Reardon says:

    For the denim skirt, I like the Talbots one and for the trench coat love the Sam Edelman style

  4. Linda Williams says:

    I Love the knee length. I’m short so I feel like it will be more versatile for me. I feel like when I wear a midi or a maxi my legs get all tangled up in denim. Plus I can move better. Thank you for posting this. The outfits you put together are Very Nice.
    Linda Williams

  5. Diann Campbell says:

    Greetings and Blessings ❗I enjoyed reading your blog. As a 78yr. gal, I wear my denim skirts just below my knee- with tights, and petite midi—@5 feet, often needing them shortened. …..with sandals, sneakers, flats, wedges & boots….. whatever the weather dictates.(same re jeans). I’ve read that the denim skirt is a popular item @ this time –’23/’24. I’ve worn them for 50 years or so…..I really enjoy the stretch denim❗🤗

  6. I love the Word of God you added!

  7. I love them all. You look good in everything!!!

  8. Nancy Fix says:

    I’m enjoying your site…plz sign me up for the “Gurls”

  9. Judy Mikel says:

    I love the knee length skirt. love the blue tank and the sage green sweater. I like the shorter skirts cause I have seen so many women walking in the long ones and to me they have to walk strange. I’m a very big shoes and purse lover. love the purse !!! Now as for the flats, I would have used a pair of mules or some brown saude cowboy boots. I notice in first picture you shoe fell off your heel. I’m thinking you could use some mules especially if your flats fit you different, now the second pair of flats fit you so much better. But thank you for giving me ideas on how to wear both skirts.

  10. Gina Price says:

    I love the knee length darker denim skirt the best.
    I will say they all look good on you though.

  11. Katherine says:

    I love the knee length denim. The others seem like they’d be too heavy feeling.

    1. I like the knee length one too.

  12. I couldn’t pick out a favorite, as I liked them all! You have a unique sense of style. Denim seems to outlast all the fashion fads & never goes out of style. I can safely say I never outgrew denim. I’ve been wearing denim since childhood when they called jeans dungarees! Yeah, I’m denim addicted. Would love to see another denim post from you.

    1. Gramzie, I’ve got more denim posts in mind. Lol!

    2. I love these denim skirts and I’m excited for the maxi. I looked for one last year and couldn’t find one I liked in my size. I’m sure I’ll have better luck this season. I have a question, once it gets colder, can tights be worn under denim skirts? I mean I know they can be worn with them, but should they be and will they be on trend without looking goofy? Wayyyyyy in the past, I’m sure I wore them together, because I grew up in the North and was much younger, but I’m wondering about this season?

      1. Jackie, you can wear the skirt either way. In the winter, lots of people wear tights with skirts and dresses to stay warm.

  13. Love your last look! Skirt ,tank, sage green sweater!

  14. Dominique says:

    Very put together. You look fantastic! The pieces work well as outfits and this article has me wanting to go out and buy, buy buy!

  15. Love denim skirts especially in color

  16. Jayne Finkbohner says:

    Tania I love you in both denim skirts. I still have my Gap midi skirt from late 1990s or 2000s. It is identical to the one you are wearing. I don’t know why I hung on to this skirt other than I guess I really loved it. After seeing you in yours, I’m so glad I kept mine.
    Loved your story about your coke, Excediren and a nap. Too funny!

  17. Kathy Moreno says:

    I’m loving the denim skirts. I think I’m too short for most. I’m 5 ft. even and can’t pull of the long skirts but loving the knee length. thanks for sharing your ideas. ❤️

    1. You’re welcome! ❤️

  18. I am torn between the midi and the knee length.
    Great article

  19. I’ve always loved a denim skirt. Bummed that I got rid of my midi from many many years ago. The Loft midi seems to be sold out currently. Found one at Kohl’s that’s similar though. Thanks for the denim skirt inspiration.

  20. They are all pretty amazing and you styled them well. It just depends if you are in the mood for long, short, darker wash etc. they are all great!

  21. I like the short one, but I think that’s mainly because I like the darker wash on it. They’re all cute!

  22. Love the Talbots knee length skirt best. Looks great on you!

  23. sue koren says:

    I think the knee lenght ones would be easier to walk in

  24. I prefer the Talbots A-line skirt

  25. The midi skirt is my favorite. I have always loved wearing white tennis shoes with a denim shirt.

  26. thanks for the post on the denim skirts. I only wear the short style. you look great in the short and long styled. the best

  27. A denim skirt is my all year long go to – I love them with sandals and a tee, with boots and a sweater and even with a silky blouse and heels.

  28. I hope you feel better very soon. I have migraines and this yucky weather puts me in the bed! We’ll pray for non-overcast days, lower temperatures, and less humidity. I love all the denim skirts!

    1. Thanks, Delanie! I’m glad the front has moved on.

  29. Paulette Levy says:

    You look great in all length of skirts!! I think a white tee and denim jacket
    ( contrasting denim tones?) might look cute with that shorter skirt you’re modeling.

  30. I like the last outfit the best. So cute on you, and I agree that sage and navy look great together.

  31. Love the denim skirts!

  32. Love the denim skirts!!

  33. CyndeeKay🌻 says:

    Knee length for me. Love wearing a denim skirt with a cardigan and flats. Perfect fall outfit for Florida🌞

  34. I like the looks of the short one from Talbots best but I think the mid length one might be the more comfortable. Long enough to cover you up but easy to walk in.

  35. Hmmm not sure I’m ready for this trnd

  36. Love the knee lengths on you. I’d have to have the midi. I agree on the navy and sage combo. They look great together.

  37. I like the shorter one

  38. Elaine Haynes says:

    I like the midi length best on you!

  39. Jan Rayner says:

    Ooh, I love the A-line skirt with your combination of navy and sage! At 5’2″, the longer skirts would just make my legs look even shorter, but they look great on you. Thanks for sharing ways we can stay current and fashionable!

  40. Ginger Hiller says:

    Even though denim skirts are not my thing, you look nice in all of them. My favorite one that you shared is the one from Talbots. I would think that short boots would also work with the full length one. I’m glad you slept last night.

    1. Thanks, Ginger! I’m so glad to feel better.

  41. Billie Henderson says:

    You are so cute in the outfit’s you put together. I just don’t like it when you send us off to another place, totally unsatisfactory, when it’s your suggestions we’re after!

    1. I’m not sure what you mean…

  42. I agree with these comments. I am also glad to see the knee length skirts. Though I like the midi and longer versions that are coming back in style, I’m only 5’4” so those tend to swallow me up. They just don’t work on my frame and aren’t flattering.

  43. I have 5 knee-length denim skirts! Obviously, I love skirts, and denim fits my SoCal lifestyle. I wear them with sandals, ballet flats, wedges, and knee-high boots. I have ankle booties but, I can’t bring myself to wear them with a skirt! I think booties with a skirt or dress can be a cute look but I don’t like the look on me. Thanks for the inspiration.

    1. You love denim like I love denim! 🙂 Thanks for taking the time to comment.

  44. Unfortunately, I like the one that is almost sold out. I guess everyone else does, too!

  45. I love the midi length! My mini days are behind me, and the maxi just feels like it would be too hard to style.

    One question about the bodysuit—does it have a thong or a regular closure? Thanks!

    1. Sarah, the bodysuit has a regular closure. Most of the time I just tuck them in instead of actually snapping them.

  46. Susanna Ann says:

    Your denim skirt outfits are so well put together. They look very stylish and can be accessorized to look fancy or casual. I love it!

  47. I loved both the knee length versions. So cute on you.

  48. I like the first skir, the mid length. the best. I’m 5’8″ and everything knee length is over the knee for me. If you find a denim skirt you like, grab it. They are so popular now that they are selling out fast.

  49. Donna Rodman says:

    I love denim skirts and the ones you showed are no different. As usual the styling is spot on. Thanks Tania

  50. First off, I really look forward to your blogs. You show so many different styles with affordable pricing too. Thank you for all you do for us gurls. I really like the last look. I’m always looking for stylish belts and didn’t see a listing for the brown one. Where did purchase that belt from? Thanks again for all you do. Nadine

    1. Nadine, that belt is so old that I can’t find it anymore. I’m actually looking for new belts, so I can link to them for everyone.

  51. I did denim skirts when I was much younger, not sure if I’m ready to try again. The skirts look great on you.

  52. I think the first is the most flattering length – at least for me.

    1. Wow,some things really are worth saving / storing, like my Jean skirts from nineties. My girls laughed and now they are asking if still have them. Longer skirt still fits me( after loosing couple lbs)
      I personally like the longer ones, feels more dressier to me.
      I like the first high waist midi skirt you have on, beautiful 👍🏻

      1. Wow, you still have your skirts?! That’s awesome!

  53. My favorite is the Talbots knee length skirt with the cardigan! So cute!

  54. The last one with the sage green sweater is my favorite. Seems like it would work I’m all seasons. I do remember wearing a long one way back when.

  55. I love the knee length skirt. I am only 5’2” so anything longer looks frumpy. I recently bought a knee length and can’t wait until it gets a little cooler.(our heat index has been 106)

    1. Wow! That is HOT. I hope it gets cooler where you are soon.

  56. I like the midi length for myself most of the time but I would wear the knee-length with tights, booties, and a fitted sweater when the weather is cooler. Love that they’re back in style!

  57. I like the NYDJ skirt the best. The Talbots skirt is in 2nd place. I agree that knee length is the most versatile. But, you look chic in all of the outfits you styled.

  58. Kathleen Marie Elliott says:

    Definitely knee length! Although, the midi length runs a close second!

  59. Gina Luebke says:

    I bought a knee length denim skirt this summer and was surprised how comfortable it is. With that being said I feel like I see the midi and maxi lengths more this fall, do you think knee length is still trendy?
    Thanks Tania!

    1. Gina, knee length is always appropriate since it is a classic style. You’ll see more maxis and midis this year because they are trending and they look great with boots.

  60. You did a great job styling these skirts. These are all looks I would wear.

  61. Cindy DELEONARDIS says:

    I’m so happy to see the denim skirts back with so many styles. I like the knee length and the one in your first picture for more for an evening out shopping or dinner with taller boots. Sage is a beautiful color and now I have the ideas how to layer it. Have a blessed day.

  62. I like #4. I’m a sucker for darker denim and the pockets are so cute.

  63. Pamela Marvin says:

    I like the knee length skirt. I am not sure how the others would look on me, don’t want to look frumpy. You styled them with flare and they looked good. I will need to check them out.

  64. Donna Ingalls says:

    I like the NYDJ denim skirt the best. Shorter length is what I’m buying this season.

  65. Love the last skirt from Talbots and how you styled it! Funny how what goes around comes back around again like the body suits.

  66. Susan Stacey says:

    I loved my denim skirts back in the day so I’m ordering the longer version (it covers a lot of flaws) from GAP. Really liked the midi version but completely sold out. Not sure about shoes yet . Thanks for doing the research for me.

    1. Glad you found something you like, Susan! ❤️

  67. Love the versatility of my denium skirts! U look great!

  68. Mary Green says:

    I like the Loft one but I’m 5’3” and even petite would be too long on me …. Still searching for this style for my height. Ideas?

    1. Well, I have a post for petites today, maybe that will help.

  69. Suzonne Johnson says:

    I love the Talbots denim skirt and the sage green sweater with the navy tank. You give gray ideas about pairing colors. I’m a matchy-matchy person and you help me break out of the box. Thank you!

  70. Thanks for styling a variety of lengths. Wish I had kept my old ones 😆 (like they would still sit!)
    Any white top with a jean skirt is hard to beat! Thanks!

  71. I like the knee length skirt the best! I haven’t worn a denim skirt in years bur you’ve inspired me to go out & buy me one🤗

  72. I absolutely love your style! I’ve followed you for many years but never commented on your posts. I’ve ordered several items you’ve shown and was never disappointed- loved them all!

    1. Yay, thanks for commenting finally! ❤️ Glad you’re here.

  73. My favorite definitely is the last on from Talbots! Much more youthful and versatile. I also love the darker wash of the skirt. Reminds me of one I had many years ago. Since I have problem feet, I think this one would be easy to style with any shoe or sneaker. If I did want a longer skirt, I’d choose the first one from Loft. The slit up the front took away from the heaviness of all the denim. The length in the petite seemed right also. Thanks for the denim skirt try-ons!

    1. So many people love the Talbots! Thanks for commenting, Cindy.

  74. Cindy Deans says:

    knee length is the best. probably the most versatile too.

  75. I like the first and last one best. I am short, so the last knee length would work best for me. I thought my days of denim skirts were over, but I’m rethinking it!

    1. Teresa, all fashion seems to come back around if you wait long enough. Lol!

  76. Penny Smith says:

    Love the shorter denim skirts.

  77. I liked the first skirt and the last skirt the most. I feel like the maxi makes you look shorter but thats what happens alot with these trends….I like them but they are not always so flattering. However you are able to pull it office. Let’s she what they look like with some boots! As always looking good!

    1. I like to show lots of trends because we are not a one size fits all. Some I like better than others, but that’s because it works for my body shape.

      1. I can remember when a denim skirt (or any skirt really) was a fashion staple in my closet.

  78. my favorite was the full length one. I have a knee length one already, so technically that might be my favorite?? But I am already planning on going to the gap near me to try one on.

  79. Lol, I should’ve kept my denim skirts from 20 years ago! My favorite is the knee length from Talbots. I really like the midi length but the front slit goes a little high for me!

  80. Linda Shearer says:

    Love the first skirt on you the mid length.

  81. Dana Smithmier says:

    Oh i used to love denim skirts in the early 90s❤️. I dont know if im ready for a redo😁

  82. I bought the denim skirt from the Loft. Looking forward to wearing it this fall

  83. Connie Eckert says:

    The knee-length skirt on you is my favorite. I plan to pull mine out of the closet and wear it soon now that I have seen you style the skirt. Thanks!

  84. I am certain I have a denim skirt in my closet somewhere!? think I am a midi fan for fall – I am guessing it would look cute with some boots or booties! You look great in all of the lengths.

    1. That was what I was thinking too!

  85. Julie Shutt says:

    My pic would be the knee length denim skirt.
    Not sure on the body shirt, lol

  86. I loved the Talbots knee length the best! Liked best with the light colored shoes too.

  87. Stephanie says:

    I like the shorter lengths of the denim skirts. I am short so I think the midi or maxi lengths would definitely look frumpy on me. I found a denim skort that works really well. I might try some of your styling tips with it to change up my look.

  88. I don’t wear skirts very often. Thanks for the suggestions on what to wear with them! I like the shorter length, but all of them look great on you!

  89. you look great in all of these. very cute skirts!

  90. Sheryl Kelton says:

    I love the maxi skirt and think it would look fantastic with boot! Sage green is such a beautiful color

  91. Talbots A-line! Wish I could wear denim skirts to work 🫤

  92. I like all the denim skirts. I bought my denim midi two years ago. I didn’t know it wasn’t in style then. I have never thought of them as frumpy if you style it right. I wear mine with sandals now and later will with boots. I remember bodysuits. I didn’t problem with them. Maybe I will try one. The Talbot skirt is one I’m going to keep an eye on.

    1. Yes, Terri! It’s all about the styling.

  93. I had a maxi high waist denim skirt with a slit up the back many, many years ago. One of my favorite and versatile pieces I had in my closet.

    Really like all these skirts.

  94. Every girl needs a good denim skirt, love all the good options.

  95. The A-line skirt from Talbots is definitely my favorite on you! In the winter you could wear it with tights and high boots!

  96. Nancy Steinke says:

    You style everything perfectly, and give me so many ways to add pieces to my wardrobe without breaking the bank. I love the high waist a-
    line denim skirt the best, the bodysuit, and the sage green cardigan. I am long waisted, so I will see if the bodysuit fits when I order it. Thanks so much!

  97. Every outfit looks very nice. The one denim skirt I would choose for myself is the button a-line. I love the light weight crew neck with the skirt especially the beautiful color.

  98. Pat Reeder says:

    love the denim skirts. For me, I would get more use out of the knee length

  99. My favorite is the one from Talbots. I prefer the shorter length.

  100. Debbie Price says:

    The A-Line denim skirt is gorgeous. I would buy all of the denim skirts if they looked as good on me as they do on you.

  101. The knee length denim skirt for me. I always had one in my wardrobe way back in the day when they were on trend. Happy to see them back! Also , I’ve always been a fan of bodysuits and thrilled to see them coming back as well. I remember them in the 70’s when I was a teenager!

    1. Same! I’ve always been a fan of denim.

  102. My favorite denim shirt is the midi length. I don’t have good looking legs so I need a little more coverage in a skirt.
    I really like the bootcut yoga pants at a great price. I just ordered the black pair.

    1. Awesome, Barb! Glad you found something you like!

  103. Love the Nydj skirt. Although, they all look great on you. Good luck to all us migraine sufferers this week. it’s gonna be a rough one with these two storms. 🥴

  104. Love the first and short a-line! But they all looked good. Such a classic look.

  105. I really like the way your styled these denim skirts. I have one in my closet. I just don’t know if I can bring myself to wear them again.

  106. I love the Talbots knee length skirt!

  107. Length of skirt would depend on the occasion for me. All look great!
    BTW – PastTense works for me!!
    Have a Blessed Day!

  108. Kelly Brooks says:

    Loved the knee length going to get the outfit. Really was darling.