Casual Shoes that go with Skirts!

Please don’t let shoes stop you from wearing skirts! I hear a lot of ladies say they don’t wear skirts because they don’t know what shoes to wear. Let me tell you something…

Growing up we were not stylish with shoes. We wore what we had to wear with our skirts. I went through a a few years as a teenager where my feet hurt all the time. I was fitted for special orthotics, and could only wear tennis shoes with them. So during the week I wore regular Nike or Reebok tennis shoes with my skirts or dresses. Did it look cute?


Not at all!

Did it make me stop wearing dresses?


If you have a conviction, and want to dress a certain way, just do it. Don’t let something like shoes get in the way!

That being said, there are good quality shoes that you can wear that look better then then a standard tennis shoe! If you have feet problems, you might not have a closet full of shoes, but if you invest in just a few good pairs they should last you awhile.

Comfortable Walking Shoes with a Skirt (Source)

These look like comfortable, basic walking shoes, and they are worn with a maxi dress!

Vintage dress with Keds(Source)

A vintage dress with blue Keds! She looks lovely.

Flats from Payless Shoe Stores

These flats from Payless are super affordable, but have really good reviews!

Bongo Woman's Flats

I’ve heard good things about these Bongo flats from Sears. They are not expensive, and the reviews say they are really comfortable. I would wear these everyday or to church.

Floral Shoes (Source)

These are so feminine looking!

Brown Mary Jane Shoes

I wear Mary Jane shoes quite often. You can look through many different styles of Mary Jane shoes on Kohls.

Circle skirt with flats

A lovely outfit with flats.

While spending money on good quality shoes can be an investment, think through how much you are on your feet. Some ladies can get by with cheaper shoes, others have to purchase higher quality shoes. Other good quality brands are Merrell, Keen, Born, and Toms.

Do you want to see what is on my wish list?


I really want to try a pair of TOMS crocheted shoes! They are so cute.

Winter is coming up on us and it does change the shoes we wear (unless you live in Florida and don’t get snow!). If we don’t have snow outside I will still wear Mary Jane style shoes with thicker socks, but I wear a lot of boots in the winter time. The next post will be about skirts and boots, so stay tuned!

I’d love to hear what your favorite everyday shoes are! 

24 Comments on Casual Shoes That Go With Skirts

  1. I have really enjoyed reading about your modest wardrobe. I recently like oct 2 have decided it was time to start my life over and dress modestly, be chaste and put Jesus as center of my life like I’ve always wanted to, Im only 25, but feel 40 haha. And now I can. I didn’t know God let you press the RESET button whenever you were ready to. And I have to say that reading your blog esp. Modest clothing has been such a huge blessing, I can find it all in one place! Skirts, shoes, examples, everything. Thank you so much for what you do. <3

  2. My danskos are my favorite. They’re pricey, but I’ve had mine for five years. They’re still in great condition and they’ve always been comfortable. I also like my Mary Jane’s, boots and my flats. And in the winter, sometimes I just wear my slipper shoes around the house! They feel wonderful and look nice enough (they honesty look like shoes) that I can even run a quick errand in them. Thanks for this post today!

  3. I bought 2 pairs of Toms from Zulilly this summer for a great price! They have had them for sale a few times since I joined. Try it out! 🙂

  4. I love the pictures you posted for inspiration, especially the ones with pretty, feminine tennis shoes! I live in an area where there are a lot of apostolic Christians that are known for always wearing skirts but I see many of them also wearing clunky tennis shoes that just don’t look feminine. I love what you are doing to encourage women to not only wear skirts, but to do it femininely. Since reading your blog I have tried to be more careful about my own shoe choices. What I struggle with is, this time of year, my legs are a little chilly, but not chilly enough for fleece leggings, and I think socks look a little dorky 🙂 with shoes and a skirt, and I am not warm enough (or comfortable enough) in panty hose, so I still am not quite sure what to do when it’s 50’s-60’s weather. Suggestions?

    • “Poof” brand makes a lightweight legging that would possibly work. They come in a couple of different lengths. I usually find them at TJMaxx.

    • I wear tights. They come in various thicknesses for different temperatures. There are some as thin as pantyhose and I have some that are cabled wool that are as warm as fleece leggings. Cabled tights look especially nice with tweeds and woolen skirts.

  5. So many cute ones! I agree that chunky tennis shoes just don’t look very feminine with skirts. I have a pair of Toms – sooooo comfortable and the crocheted ones are really cute!

  6. I wear Sanita’s (Dansko style – they were the makers of Dansko’s until Dansko outsourced to China a few years ago)daily for the arch and heel support, usually a Mary Jane style. I usually buy them online for around $40 in stead of the usual $110. They go with everything!!

  7. My everyday shoes are flip flops! I actually prefer barefoot, but our entire home is currently concrete. I need some cushion, and am loving my Crocs flip flops!
    Another casual option are boat shoes. They can be feminine and cute with skirts. My little sister even has pink ones. Mine are camel brown.

  8. Thank you so much for these posts. They have been very encouraging to me. Especially the one on denim skirts! I wear them but worry about wearing them too much.
    I have Bobs shoes which are cheaper than Toms and I love them. They are so comfy and look great with my skirts!

  9. I usually wear flats, flip flop(on occasion), and wedges for summer. Boots, wedges and ballet flats for fall/winter. I usually never wear tennis shoes, not my favorite.
    For cold weather, I , allot of the time will wear a knit skirt , just below the knee with full length leggings and ballet flats. And I always stay warm!!

  10. TOMS (I have a black sparkly pair that are easily dressed up or down), KEEN sandals, and flip-flops are my go-to shoes to wear with skirts. I struggle with awful flat feet and loose ankle joint, but put orthotic inlays in the KEENs and TOMs, and invest in the Vionic brand of flip-flops. They are great!
    I don’t care to wear tennis shoes with a skirt, but I will wear that combination just doing housework around the house.
    I don’t feel like I can move very easily in boots, but I wear them to church in winter.

  11. So far, I have not been able to find anything other than clunky tennis shoes to wear with skirts. I have very bad feet with no padding in the ball of the foot. I have orthotics, but unless the shoe is very well padded like a running shoe, I have severe pain in the ball of the foot. I have tried very expensive shoes, but they still have too little padding. I also have very narrow heels, so I have not been able to try clogs. They just fall off. Ideas?

  12. In the summer, I wear sandals, in the fall, I wear Mary Janes or other slip-ons, and lace-up Packer boots, and in winter I wear lace-up hiking boots with tights & tweed socks!

  13. I also love crocs! They have some really cute flats styles now, not at all clunky like the original crocs are. They feel so comfy all day!

  14. Alegria saved my feet!! 2 years ago I went to the Dr with bad heel pain, couldn’t hardly walk in the morning. HE said I had plantar fasciitis. My Dad who runs a shoe store said to try Alegria; oh wonderful!!! NOT really pretty; but who cares if you’re feet don’t hurt. I try to find them on sale at!!! I’M pain free most days now. WEAR them with skirts and jeans!!!

  15. Thank you for your “as always” very encouraging post. I have chosen skirts and jumpers for my wardrobe choice within this year. After a severely broken ankle, 5 surgeries including final fusion, I now have to wear a special orthotics on my ankle of the opposing leg so my shoes have to be lace up shoes, so I wear SAS which are very expensive but after my first purchase at the SAS Store I found 2 pair of “like new” on EBay. Before this I had a closet full of beautiful high heels and very nice flip flops. The Lord has shown me to stop with my high heel collection &I flip flops. LADIES BEWARE OF WEARING FLIP FLOPS all the time. Not only can you ruin your feet but when they go bad, so goes the ankles with them.

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