How to Style A Denim Maxi Skirt if You’re Over 50

Have you been seeing the denim maxi skirt everywhere but are over 50 and stumped as to how to style it? It can be tricky. So many inspirational photos feature 20-something girls wearing them with a bra top and layer. Not for me. Today’s post has five phenomenal denim maxi skirt looks for you to check out!

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Over 50? How to Style a Denim Maxi Skirt

Tips When Shopping for a Denim Maxi Skirt

Fitting denim skirts can be a bit tricky. Below are a few things you should look for when shopping.

  • A front, back, or side slit to make walking easier.
  • The proper fit. Ensure your skirt is comfortable around the widest part of your body (often the hips/rear). If need be, alter the waist to fit more snugly but do not buy a skirt that is pulling across your widest spot.
  • Your ideal length. A skirt that hits low calf to an inch or two above the ankle will likely be the most flattering
  • A comfortable fabric. Denim can be heavy. Be sure to choose a skirt that is light enough for warmer temps and that won’t weigh you down unnecessarily during the day.
  • Keep proportion in mind. A classic, slightly a-line shape will suit most people. However, if you choose a more fitted, pencil style or a full flared/circle style, remember: the wider the bottom, the more fitted the top and vice versa.

A few of my favorite denim maxi styles are below. A black or white version marks a nice change from traditional denim blue.

Sporty Style

A sporty style is great for those of you who work from home or for running errands throughout the day. The tape trim on this lilac hoodie (which also comes in Kelly green) adds a nice detail and ties in with the striping on the classic Adidas Samba sneakers.

Denim Maxi Skirt Outfit

Polished Casual

Perhaps you’re meeting a friend for lunch or heading out to the mall. This polished casual outfit fits the bill! It pairs a classic white button-down with a quilted vest, chunky loafers, and a leopard print handbag. If the weather is especially cold, add some tights and swap the vest for a quilted puffer jacket or pea coat.

Denim Maxi Skirt for Over 50 Style

Business Casual

Do you have an office day planned or maybe you’re a teacher? This business casual look is both chic and comfortable. Pair a turtleneck with a blazer, add a belt and mid-heel bootie, and out the door!

Note: The clear and gold earrings are available here.

Denim Maxi Skirt for Over 50 Style

Urban Elegance

This fourth look is a slightly elevated version of business casual. The paler tones and feminine vibe of the lady jacket and slouch boots convey an upscale vibe. Finish your outfit with a killer bag (J. McLaughlin makes a great dupe) and jewelry that complements the buttons on the lady jacket.

Resort Style

Lastly, you may be heading out of town for a winter break. A denim maxi skirt works well with summer styles too!

Denim Maxi Skirt Outfit

For more inspiration on how to wear your basics and beyond, check out our How to Style It series.


Tips and inspiration for cultivating a simple, stylish and satisfying life!

Have you been seeing the denim maxi skirt everywhere but are over 50 and stumped as to how to style them? It can be tricky. So many inspirational photos out there feature 20-something girls wearing them with a bra top and layer. Not for me. Today's post has five phenomenal denim maxi skirt looks for you to check out! #denimmaxiskirt #longdenimskirt #over50style #stylingtips
Have you been seeing the denim maxi skirt everywhere but are over 50 and stumped as to how to style them? It can be tricky. So many inspirational photos out there feature 20-something girls wearing them with a bra top and layer. Not for me. Today's post has five phenomenal denim maxi skirt looks for you to check out! #denimmaxiskirt #longdenimskirt #over50style #stylingtips

2 thoughts on “How to Style A Denim Maxi Skirt if You’re Over 50”

  1. Hi Betsy. This post gave me so e great ideas on how to style my denim skirt that I bought in Strasbourg, last year. I must say that the denim skirt is very versatile, and is especially great for the more casual lifestyle that we lead here, in this country. Thank you for sharing. xx

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