How To Style A Circle Skirt Outfit for Women Over 50 High And Low

One of our favorite new trends for Fall 2023 is actually an old one! The 50s style circle skirt has circled back. This classic skirt style is easy to wear for women over 50. Designers including Christian Dior, Carolina Herrera, Prada  showed circle skirts on the runway with simple and easy styling. I styled this amazing leopard print Valentino Garavani circle skirt with a basic black scoop neck top, black slide mules, a punchy pink clutch bag and a simple gold cuff bracelet. I also mirrored this high-end designer look with a much lower priced version, so you can wear it high or low, or mix up the pieces. Here’s how to wear a circle skirt outfit for women over 50 both high and low.

fall 2023 fashion trend circle skirts
Christian Dior, Carolina Herrera and Prada Fall 2023 RTW

Fall 2023 Circle Skirt Trend Styling Tips

This season’s circle skirt should be styled with more ease than in the past. You can avoid belts or excessive jewelry to get this laid back yet still elegant and chi look.

1. Wear a clean and simple top or thin sweater either tucked in or left out just over the waistband. A fitted shirt or blouse works well too, as long as there is not a lot of volume to tuck in around the waist line.


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2. Point toe pumps, kitten heels, mules or ballet flats (yes it is a nod to the 50s) work well with midi-length circle skirts. Try a bow pump, ankle strap or other embellishment.

3. A clutch bag works best with a circle skirt. You don’t want to carry a big clunky bag or a shoulder strap where the bag will get buried in the volume of the skirt.

4. Keep your jewelry to a minimum when wearing a circle skirt. You will notice on the runway the models were void of jewelry, and any embellishments were mostly on their skirts and shoes.

How To Style A Circle Skirt Outfit for Women Over 50

circle skirt outfit for women over 50

Shop the high end circle skirt outfit on the left, or the low priced version on the left, or mix up the pieces for what is known as high-low styling.

The Leopard Print Circle Skirt

This Valentino Garavani Leopard-print silk midi skirt is absolutely gorgeous. The interesting light to dark graduated leopard print, the fabric, the drape, the craftsmanship and fact that it has pockets would make this a worthwhile investment for your wardrobe. However $5,900 is a steep bill to pay (I think I once bought a car for that price) so I found a budget-friendly option, but without all the awesomeness. This “Beverly” Button Front Full Circle Skirt from Etsy is only $52.08 and it actually has pockets too. 

Black Scoop Neck Top

A simple scoop neck black jersey top like this long sleeve Raya from The Row can be tucked in or worn casually over the skirt. This is an extremely versatile high quality investment top for $590. But you can get the look for less with this Caslon® Scoop neck long sleeve cotton knit top for only $25.

Suede Kitten Heel Buckle Mules

The runways showed circle skirts with lower heel point toe pumps, both with and without embellishments. These Manolo Blahnik Maysale 50 black suede mules will be perfect for this look and are worth every penny for $795. You will be sure to wear them time and time again. However these DSW Journee Collection Vianna mules look similar (at a real quick glance) and will only set you back $59.99.

Barbiecore Pink Clutch Bag

A simple clutch bag works well with a circle skirt and why not add a pop of color with this Valentino Garavani VLogo textured-leather wallet for $1,350. After all Valentino started the Barbiecore trend several seasons ago with this vibrant color, so this bag would be an excellent addition to your wardrobe and will retain its value. Yet you can get the color for less with this hot pink Jewel Badgley Mischka Harper satin envelope clutch handbag for $80.

Simple Gold Cuff Bracelet

A more modern way to wear a circle skirt is void of excessive jewelry. A simple cuff like this David Yurman Cable Spira bracelet in 18K gold adds the right finishing touch for $1,750. But if you don’t want to invest in fine jewelry this BaubleBar Lana cuff bracelet has a similar texture and feel for only $44.

Shop This Circle Skirt Outfit


Valentino Garavani Leopard-print Silk Midi Skirt, $5,900

The Row Raya Long Sleeve Scoop Neck Jersey Top, $590

Manolo Blahnik Maysale 50 Black Suede Mule, $795

Valentino Garavani VLogo Textured-leather Wallet, $1,350

David Yurman Cable Spira Bracelet in 18K Gold, $1,750

Total High End Outfit: $10,385


Etsy The “Beverly” Button Front Full Circle Skirt, $52.08

Caslon® Scoop Neck Long Sleeve Cotton Knit Top, $25

DSW Journee Collection Vianna Mule, $59.99

Jewel Badgley Mischka Woman’s Harper Satin Envelope Clutch Handbag, $80

BaubleBar Lana Cuff Bracelet, $44

Total Low Priced Outfit: $261.08

Do you like the circle skirt trend for fall 2023? How would you style it?

Carol Calacci

Runway photos:

You may also like to read Best Fall 2023 Shoe Trends for Women Over 50: From Runway To Real Way and Red All Over: Top Fall 2023 Fashion Trend for Women Over 50.

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