What Are The Best Shoes To Wear With Joggers For Fall?

Lauren and I were recently chatting about how much we love joggers and how we intend to wear them this fall. Then I questioned what shoes should we wear. To quote myself back in June, I said “anything goes” in my post on the best joggers for women over 40. However, now as we head into fall and winter I felt the need to take another look at the trend. Since we won’t be wearing slides, sandals and mules as we did last spring, I came up with list of the best shoes to wear with joggers for fall.

Best Shoes To Wear With Joggers for Fall

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J Brand Arkin Cotton-blend Sateen Track Pants, $230


Sneakers are an obvious choice, and yes, you can certainly stick with your sneakers for fall. Bare ankles do look best with sneakers and joggers, so you may not be able to wear this look for long as the weather gets cooler in some parts of the country. You can opt for sneakers in darker colors, heavier leathers and textures, even pony hair. Slip-on loafer-type, high tops, old-school styles and boot sneakers all work well with joggers.


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Olivia von Halle Gia London Silk and Cashmere-blend Set, $1,275

Chelsea Boots or Combat Boots

An easy substitute for your sneakers is to wear a Chelsea boot or combat style boot with joggers. A rubber lug sole keeps the elements out and keeps you comfortable for fall. The casualness of these boots go with the street-style sportiness of joggers. Boots like these look fabulous with faux leather joggers.

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Madeleine Thompson Working Girl Cashmere Track Pants, $395

Flat Shoes With Joggers

Flats can be quite tricky because you run the risk of looking like I Dream Of Jeannie (or Barbara Eden in the show).

I dream of jeannie barbara eden harem pants

Modern flats with gathers or square toe shoes will give your joggers a new look for fall. Here are some examples.

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Saint Laurent Lurex Track Pants, $1,590

High Heel Ankle Booties

Sleek and slim high heel ankle booties are your best bet for a dressier joggers look for evening. Find boots that are tighter around the ankle so the joggers will lay over the shaft. You don’t need to wear super high heels, either. Kitten heels or lower  heel booties are other options. See more here.

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J Brand Arkin Sateen Joggers, $228

Slouchy or Western Style Boots

Another option is to wear a slouchy boot over your joggers. This works best with a slimmer fitting pair of joggers. (Do not wear knee high boots!) You can also try other western inspired boots with joggers as well.

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Stella McCartney Julia Stretch-Cady Track Pants, $575

Creative Pumps

I saved the trickiest shoe for last, but you can wear a variety of pumps with joggers. Get creative with animal prints as shown, cone heels, d’orsay or strappy pumps. You really need to try them on and see how they look. A little confidence may be all you need! Here are some styles you may like.

Joggers Styling Note: When you purchase joggers, look for slimmer fitting styles similar to the selections I have shown you. Joggers that are not too billowy or voluminous in the leg and around the ankles are more flattering and also much easier to style with shoes.

What kind of shoes do you like best with jogger for fall?

Carol Calacci

You may also like to read more style over 40 posts like The Slouchy Pants Trend To The Rescue and The Latest Fall Pants Trends For Women Over 40.

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Photo: “I Dream of Jeannie” studio publicity shot, Barbara Eden, 1966

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