You are currently viewing 3 Tips to Look Great in Sneakers with Skirt
Zoom-in on polka dot Keds (own)
Sneakers with skirts or dresses are a big street style movement right now. This post covers how to adopt the 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.
  1. How to Wear Sneakers with Skirts in Midlife
  2. How to Adapt the Skirt/Dress with Sneakers Trend over 50
  3. Sneakers Are Risky with Skirts

Disclosure: There are affiliate links in this post.

How to Wear Sneakers with Skirts 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 watch to wear them in a modern way, not as we did in our teens or twenties. I showed how to style sneakers to look polished as Karlie Kloss does when she wears her sneakers. Here is how to pair them with a skirt for a Right-Now modern look.

  1. When wearing sneakers over 40, it is key to stay out of the cute girl territory – think Taylor Swift. Of course, I think she wears them lovely with her Romantic Style with floral print fit-and-flare dresses. Nevertheless, I would not wear these Keds with a fit-and-flare small floral print dress. Now even for swing dancing. The look is too young. If you go for a dress, take a sheath.
  2. Stay out of casual territory of wide skirts with sneakers as it could look frumpy. Instead go for serious work items like a straight or pencil skirt with a button-up shirt/top and/or a blazer.
  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.
When wearing the skirt with sneaker trend, watch the proportions. #styleadvice #agelessstyle Click To Tweet
#styleover50 woman in red white black summer look with white and plain wood patterned Winkwood eye wear
Notations top, Oliveo leather skirt, Hermes collier de chien bangle, Keds, Brooks Brothers stripes silk shirt, DIY statement belt, Celine bag (all own) and sunglasses c/o Winkwood


How to Adapt 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 throw all the body weight onto the ball of the foot. Like we loose collageen in our skin as we age, we also loose the cushioning in our feet. When you embrace the trend and adopt it, remember

When wearing the skirt with sneaker trend, watch the proportions. #styleadvice #HighLatitudeStyle Click To Tweet

red and white Keds polka dot

 Moschino belt details
Zoom-in on the Moschino belt, Seiko watch, statement ring, and print details (own)


Also accessories with statement pieces that look grown-up. Avoid everything girly or very casual. The former looks

Too Young

like in trying too hard. The latter looks like trying too hard.

Not wearing accessories looks like not caring about styling at all!

Don’t let your outfit be a random thing. Wear the right look in every situation by looking up what to wear when in How to Dress for Success in Midlife. Buy the book now.

Sneakers Are Risky with Skirts

The trend is risky. You have to avoid to look girly, which reads trying like trying too hard. You have to avoid to look frumpy, which reads not trying at all. And you have to not artificially shorten your legs.

When you are interested in another example of this tricky to wear trend, have a look at this post from earlier this week. Herein, I showed an outfit how I styled these sneakers for Casual Friday.

stylist showing how to style Keds with a skirt

over 50 years old fashion influencer in posh casual work look with leather skirt and Keds
Outfit details: Oliveo linen summer blazer with Sienna Studio leather pencil skirt, Keds, Moschino belt, and GNW cardigan worn instead of a blouse (all own)


How do you wear your sneakers? Do you wear sneakers with dresses or skirts? Do you like this trend/look? What are your fashion and style challenges?

When you are interested in reviews of the newest trends, and fashion and how to turn them into personal style, to look to your best in midlife, subscribe to High Latitude Style. Deep inside you know when I can do it, you can do it too.

Photos: G. Kramm

© 2013-2021 Nicole Mölders | All rights reserved