How to Wear Long Denim Skirts For Women Over 50: Splurge or Steal

You may have noticed that long denim skirts are on trend for fall 2023. They are in stores, on celebrities and a street style trend at recent fashion weeks. But how do you wear one when you are over 50 and not look like a tween or like you are trying too hard? I’ll show you several skirt styles that may work for your body type and tastes and give you styling options. And one of those options is to splurge on a designer denim skirt, or to get a similar look for a steal. You can decide if you want to splurge or steal.

How To Style Long Denim Skirts for Women Over 50

The best thing about this trend is you are covered up! A denim maxi skirt is comfortable, easy to wear and can make you look lean and mean. Here are some basic styling tips.

  1. Wear it like jeans. When it comes to styling, a long denim skirt can simply replace your jeans. T-shirts, shirts, blouses, sweaters and cardigans work well with long denim skirts. However when it comes to jackets it, a hip length or bomber style works best.
  2. Choose maxi or midi. Maxi denim skirts can be difficult to walk in but they usually have slits, fish tail or A-line shapes to accommodate for movement. If a maxi is too overwhelming for you, and if you are petite, go with a midi length style.
  3. The longer the skirt the higher the shoes. Especially for women over 50, it’s best to avoid wearing sneakers with a long midi skirt. A more sophisticated approach is to wear a high heel, mid-heel or kitten-heel pump, slide, sandal, ankle bootie or tall boots. These footwear styles work best with maxi denim skirts. With a midi skirt you can wear all of the above but also lower 1 inch heels or even flats.
  4. Choose a style to flatter you. By the time you are 50, you know what works best for your body type! To avoid a skirt that accentuates or is too tight in the hips, choose an a-line style or even a circle skirt. If you don’t want to show too much leg, avoid slits, or if you have fabulous legs go for it! I also urge you to try on a style you may not think will work, because it just may surprise you! Always get the proper fit and avoid a skirt that is too tight, but also if it is too loose, you may find it spinning around.

Long Denim Skirts Styling Options

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I pulled together what I think are some of the best styling options from Net-a-Porter to show you the most sophisticated ways to wear a long denim skirt.

Shop Long Denim Skirts: Splurge or Steal

And now it’s time to shop! Here are some of the best designer skirts to invest in and similar looks for a steal.

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Frayed Asymmetric Skirts

This CHLOÉ Frayed asymmetric denim midi skirt for $1,290 is a casual and very versatile investment. This skirt is easy to wear for most body-types and looks fabulous with tall boots and a sweater in fall and winter, or slides or sandals with a t-shirt in spring and summer. But you can save 90% with this Wash Lab Denim Selma Pieced Asymmetric Denim Maxi Skirt for $128.

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A-Line Maxi Skirts

This style is the easiest to wear and because you can walk in it! This amazing GANNI Maxi A-Line Appliquéd organic denim maxi skirt for $345 is super-stylish and worth the investment. Wear it runway style with a denim shirt! Or you can get this CHARTOU Women’s Retro A-Line Maxi Long Denim Skirt on Amazon truly for a steal at $33.


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Circle Skirts

Circle skirts are a trend we love for fall 2023, so why not get one in denim? This ALAÏA Archetypes leather-trimmed belted denim midi skirt is gorgeous but it is also $2,150.  However you can get a similar look for much (much) less. I found this Belle Poque Skirt Vintage High Waist Pleated Skirt with Pockets for only $20 and you can top it off with this Ayliss Wide Waist Cinch Belt Double Studded Waistband for $18.99 and get the look (well not as luxurious) for $39.99.

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Basic Front-Slit Midi Skirts

A classic style that is not quite so trendy and you will wear for years is a basic front slit midi skirt. This LOULOU STUDIO + NET SUSTAIN organic denim midi skirt is ideal for $320. Yet even more ideal is to get one for only $89, like this Steve Madden Avani Front Slit Denim Skirt.

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Ruffle Hem Denim Midi Skirts

If you want to try a denim skirt that is more feminine and flirty, you’ll love this ALAÏA Ruffled denim midi skirt for $1,730. Wear this skirt with heels for dress and clogs for a more casual look. If you don’t love the price tag, try this Allegra K Denim Jean Skirt for Women’s High Waist Fishtail Skirt for only $40 on Amazon.

Are you going to try the long denim skirt trend for fall? How would you wear it?


Carol Calacci

You may also like to read Fall 2023 Trends: Amazing Tailored Suits for Women Over 50 and Fall 2023 Trend to Try Now: Closet Staples For Women Over 50.

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3 thoughts on “How to Wear Long Denim Skirts For Women Over 50: Splurge or Steal”

  1. Love the denim skirt, especially #s 1 and 3 in your pics. I love wearing them with boots in the fall/winter, and depending on the thickness of the denim they are adorable with birks or another sandal, or some kind of flat. Honestly, I preferred the less expensive skirts of #s 1 and 3, too, provided that the thickness is appropriate. So excited to mind a new denim maxi skirt or two! (And treat myself to a couple new pairs of boots to wear with them – why not!)


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