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Remember the old school fabric sports shoes we wore in elementary school? No one would have ever imagined that one day we would wear them on the streets! Stars like Taylor Swift made them an It item. Sneakers with skirts or dresses are a big street style movement right now. But how do you adopt the sneakers trend without looking like trying too hard or not trying at all. In other words, how to style the comfy gym shoes in a stylish street style way and not look Old Lady. Read how to wear sneakers with a skirt.



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How to Wear Sneakers with a Skirt in Midlife

Sneakers are an It item this season. For those of us over 50, sneakers being an It shoe is the second time around. This means we have to wear them in a modern way, not as we did in our teens or twenties. Take your inspirations from the models like, for instance, to walk in your sneakers as polished as Karlie Kloss.


Tips How to Style Sneaker with a Skirt Right-Now

  1. When you are over 40, stay out of the cute girl territory – think Taylor Swift. Of course, she wears them lovely in her Romantic Style with floral print fit-and-flare dresses. The look is too young. Wear a sheath or shirt dress instead.
  2. Stay out of casual territory of wide skirts with sneakers as this combination could look frumpy. Instead wear business casual attire like a straight or pencil skirt with a button-down shirt/top and/or a blazer with your canvas.
  3. Keep an eye on proportions. Avoid to be cut in half. Try to arrange for three thirds: One being your legs, one your skirt, and one your upper body.


stylist showing how to style a summer office outfit with sneakers
Notations top, Oliveo leather skirt, Hermes collier de chien bangle, Keds, Brooks Brothers stripes silk shirt, DIY statement belt, Celine bag, and Winkwood sunglasses.



Why to Adopt the Skirt/Dress with Sneakers Trend over 50

Many of us women over 40 will like the trend. The flat shoes give our somewhat worn balls of the feet some rest. Wearing high heels always throws all the body weight onto the ball of the foot. Like our skin looses collagen as we age, we also loose the cushioning in our feet.


What Accessories Are Best When Wearing the Skirt with Sneakers Trend over 40?

Go for accessories that are statement pieces and look grown-up. Avoid everything girly or very casual. The former looks

Too Young

like in trying too hard. The latter looks l

like not caring about styling at all!


examples of sophisticated accessories Moschino belt and watch details Example of sophisticated accessories for a skirt with sports shoes look
Zoom-in on the Moschino belt, Seiko watch, statement ring, and print details for an example of sophisticated accessorizing.



Skirt with Sneakers Outfit Ideas

The following outfit inspirations are easy to copy and illustrate the above tips.


stylist showing how to wear sneakers with a skirt
Skirt with sneakers outfit idea for mature women


ver 50 years old fashion influencer in posh casual work look with leather skirt and Keds
Oliveo linen summer blazer with Sienna Studio leather pencil skirt, Keds, Moschino belt, and GNW cardigan worn instead of a blouse.


midlife blogger in summer outfit with 3 mixed prints old school canvas shoes
Talbot abstract floral print skirt, Keds, Hermes enamel bangle and collier de chien bangle, Loft striped sweater, Celine tote, Paloma Picasso sunglasses, Talbot abstract floral print skirt, Keds, Hermes enamel bangle and collier de chien bangle, Loft striped sweater, Celine tote, Paloma Picasso sunglasses.


Further Posts with Gym Shoe Looks outside the Gym

You can find another example of this tricky to wear trend in my post on black carbon in the Arctic.

When you are thinking about jumping the bandwagon take a look at my SUNS old school sneakers review. It not only provides outfit inspirations with a dress, but also information about what is on the market.


Photos: G. Kramm

© 2013-2023 Nicole Mölders | All rights reserved

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