I have received a number of comments and email asking about choosing shoes to go with skirts. This seems to be a big obstacle to wearing skirts and really being comfortable with the look. I would hate to let a choice of shoes stand in the way!
Go all the way to the tail end of this post for some pretty cool shoe ideas!
Update: This post dates back to 2012 when I wore mostly skirts and maxis. Because I wear jeans and slacks 50-60% of the time now, I have included photos throughout of great footwear with pants, as well.
Ideas For Flattering Shoes & Footwear
There are so many ideas of what this might look like, I thought I would try to gather some cute ideas together in one post. Here are some of my finds, and I give links back for further exploration.
In the warmer months it is much easier (in my opinion) to find flattering shoe choices to wear with skirts and dresses. Sandals, ballet flats, even simple pretty flip-flops work quite well when it is hot outside. And then when it turns chilly or cold there are also many options.
(Life As Mom ~ The Modest Mom)
Laura has sewn so many lovely, feminine summer and fall outfits, and she pairs them with just the right flattering shoes~
Boots somehow just complete this outfit!
These simple shoes do not draw attention to the feet, but, again, complete the look.
Here, the shoes kind of fade away and let the dress and the smile shine!
Some may not feel comfortable doing this, but I love this pop of color!
Crocs like these are just the thing for us when we are gardening or doing something active out of doors.
I like that you can actually hose off your feet before coming inside if you get dusty 🙂
(Susannah Dashwood Etsy)
Sandals look great with any length skirt anytime of the year. In summer wear them with your toenails painted. In winter, wear your favorite knit knee socks or tights.
How To Choose Shoes Video
I came upon this short, helpful video entitled “How To Choose Shoes for Skirts or Dresses”:
The key points?
- Get yourself a full length mirror if you don’t have one!
- Try on different shoes and see which works best.
- You can always wear a shoe that is the same color as your hair – it creates harmony and balance.
- You can always wear a ‘nude’ shoe that is similar to your skin color.
- Think about balance – thicker fabrics need more substantial shoes, very fine or flimsy fabrics need lighter, strappier, more delicate shoes.
The Nude Shoe
(source)
The Accent Shoe
It is such fun to match your shoes to one or more articles of clothing. If it tastefully done, it is a nice playful touch. I especially (with big feet) don’t like to draw attention to my feet, but it can also pull together an outfit.
(That Wife)
Deck Shoes
Canvas deck shoes are really perfect for this sporty cotton dress.
(no source)
Deck shoes are also an option with a jean skirt, etc. I found these next two outfit combinations over at the Modest Mom blog:
Ballet Flats:
Ballet flats are typically a wisp of a shoe, and if you have strong feet with no arch problems you will most likely be fine. They look adorable and feminine with skirts and dresses, and they are great for any season depending the color you get them in.
In the winter, you can wear full length panty-hose or hose weight knee-highs to keep you warm and still look cute. But, they usually have slick soles (no tread) so would not be good with little children or carrying a baby in snow or ice.
If you will be on your feet all day, you may want more support than a typical pair of ballet flats can provide. Some cushion between you and the floor may actually save you from spider veins in later years~ take it from someone who worked in surgery on concrete floors for years.
The little bows on the toe of these black low heel pumps are classic and work beautifully for more dressy occasions such as weddings and special dates with your husband. Pamper him by being at your modest, beautiful best for him. We dress for the Lord and for our husbands alone.
In the colder months, finding good shoes to go with the heavier weight woolens, corduroys, denims, and knits of winter can be a bit more of a challenge. Also, you must keep warm, so what to do? Artful Homemaking has a certain style, and you can develop your own style.
Wearing skirts a third of the time, I’ve tried a lot of different things over the years to keep warm during colder months. Pantyhose and tights work fine, but are not very warm. Sweatpants would be very warm, but make me feel bulgy and frumpy!
The best solution I have come up with is pretty simple. Wear leggings! A pair of leggings that are in style right now are the black leggings that many wear under a tunic shirt. I wear these under my skirts and dresses, and they work great!
Boots:
Don’t forget boots. Boots with skirts remind me of hearty English country women somehow (of course, out for a gallop or a sleigh-ride)!
(source)
Note the tights and boots, but you could also wear a pair of woolen socks besides for extra warmth at a football game, etc.
(Source)
(source)
~~~~~~~
The Support Shoe that doesn’t look like one
Some of you have kindly shared the companies you have been happy with and who seem to make a good support shoe. You can find thin and unstructured shoes for those with healthy feet most anywhere. These links are for those who have foot issues, but are excellent for those who don’t want to get ‘foot issues’, too!
Keen, Merrell, Børn, and Croc ( and many others like Naturalizer) offer lots of different styles. I am just scratching the surface here.
~Børn has some of the best shoes we have ever owned, but that may change as manufacturing quality goes down and prices go up. We found our first pair (sandals) at a thrift shop, and I sprayed the really good with essential oils and put them in the sun. I love the comfort, support, and quality.
~Merrell is an excellent shoe and has a whole line for everyday and for outdoors and active-wear:
~Keen for daily wear and active wear, too:
The simple Mary Jane by Crocs. Very comfortable.
Also, FYI ~check out Good Feet. “Since 1995, Good Feet Arch Supports have helped millions of customers all over the world to relieve their foot pain and be able to once again walk, work –even enjoy their favorite sports activities – pain free, for the first time in years.” We have one in our city and I have heard good things about them…
Well, that’s my humble offering, dear ladies. I hope this will be of some help to you as you consider how we can be ambassadors for our Lord to our family, our neighbor, and to those we meet on the street.
“A true woman is willing, serious, and determined to reflect the beauty and heart of Christ to her world. She seeks to live a God-centered life, trusting Him and saying “Yes, Lord!” She knows this is only possible by His grace, and seeks to do so in community.” ~Nancy Leigh DeMoss
“How beautiful are the feet of those who bring good news!”~Romans 10:15
©2026 Deep Roots at Home • All Rights Reserved
Lesley Prentice
Jacqueline, I so much appreciate this series! I grew up with 2 brothers, and I have always been some what of a “tom boy”, but always very feminine. I have absolutely no fashion sense of my own, and I always look forward to these posts to give me a visual, of how to match up certain articles of clothing. It has been a blessing to me…Thank you.
~Lesley
ChristyH
I completely agree with you on the growing up a tom boy and having no fashion sense. These posts have helped me quite a bit.
Deanna
Love this series!
I wear Clark’s mostly. Comfy and supportive yet look good with skirts.
I love the last photo in your post – so ladylike and feminine!
Deanna
Tiffany Santos
Dansko (and the cheaper Sanita brand) also makes a lot of pretty shoes for people with arch problems. Plus they go great from being worn with skirts and dresses to pants and from everyday to dressy. Ross, TJ Maxx and Marshall’s are good places to look for the more expensive brands of shoes for around $30. They usually have Born, SAS, and Merrell there.
Rebecca Ann
Jaqueline all of the tips and tricks in this post and the whole feminine dress series have been so helpful to me. Thank you so much for the time your daughters and yourself have taken to put this series together! I absolutely love the way you have presented all the tips and tricks with pictures and videos. Thanks again!
God bless you!
Rebecca
Grandmother Lois
Beautiful. I love the ideas. These posts about how beautiful womanhood looks were very inspiring. ♥ Thank you.
patsy
I love wearing dresses and skirts but last year I developed Deep Vein Thrombosis and now have to wear compression stockings! So now I wear pants most of the time!!! It’s a BIG change for me! Patsy from HeARTworks
Jessica
Lots of cute ideas. I am on the lookout for some brown winter boots.
ChristyH
I love to knit my own socks in fun yarns and they go perfectly with my one pair of Keens. My husband and I love to get our shoes from Zappos.com great service.
Jill @ Jill's Home Remedies
Great taste as always! 😉
Nicole
Good shoes are very important – I seem to have an issue with shoes. I only have two flats (silver and black) and 1 pair of sneakers. I wear out shoes so fast that way, I really need to invest some in buying more variety! Great post. I have seen some good deals on good quality shoes at stores like Marshalls, TJ Maxx and Ross.
Nicole
Grace in the Home
Petra
I love these posts, too! My wide feet make it difficult to find good quality, affordable shoes…these are great ideas. In response to what to wear under a skirt in winter-time, I like wearing flannels rolled up just below my knees and tucked into knee socks. Not much bulk, and very cozy. 🙂
Thanks so much for the thought and time you put into these posts…how is your day going? Prayin’ for you!
Jacqueline
Good morning, Petra!
We returned late last night, and I am getting a slow start, but I felt lead to leave you a little reply to *hug* you in the Lord! I pray for you often, dear one!
Joenne
You have done an excellent job putting this entire series together and it has been a real blessing to be able to view it all. So often there are hints and suggestions, but having the pictures really puts everything together. Thank you for taking the time to do this, and may God richly bless you for it!
LeeAnne, Style N Season
Hi Jacqueline,
I love these series! Modesty was prompted me to start blogging, thought I could contribute something. But I ended up receiving much much more than what I had to give! So thankful for this community of likeminded ladies.
Visit me:
LeeAnne, Style N Season
http://stylenseason.blogspot.com
Jacqueline
Thanks for stopping by, LeeAnne! I ‘like’ what I see and wish you well as you blog. Blessings to you 🙂
Jennifer P
Jacqueline~I have loved this series! It’s made me evaluate, even at my age (47), my clothes and ‘feminine dress’. I actually ‘challenged’ myself to a week of skirts, which I normally do not wear on a daily basis. I really liked it and think I’m going to incorporate them more. Not that you have to wear a skirt to be feminine, but I just felt more so 🙂 Plus I love the leggings idea…because I am always so cold during winter months especially!
Anyway, Olivia & I have been doing the ‘Reclaiming Beauty’ webinar which is a great addition to your posts that we have THOROUGHLY enjoyed. I love the pictures and Olivia is inspired 🙂
Mrs. T.
Oh, thank you :). Lovely ideas.
Heather @ourcultivatedlife
Jacqueline~Thank you so much for this series. I really appreciate your encouragement for modesty and femininity in our dress. These are such cute ideas, especially for the various shoes. That is one thing I always seem to struggle with.
Have a blessed day!
~Heather
Jacie
Yay! A shoe post, just what we needed! I do wish there were more picture idea’s of boots with skirts, though. I look foward to fall for the scarves and boots and this being my first year in skirts/dresses, I’m having a hard time pairing them up with the right boots.
hannah
TOMS can go really well with skirts to, especially denim or more casual tierd (sp?) or maxi skirts.
Jenn
I really enjoy these blogs and knowing that I am not alone in wanting to dress more feminine and my girls to do the same. I am really hitting a wall with our outside family that think we’re weird, but we love the way a dress or skirt make us look and feel like ladies. Thanks for the encouragement I get from your blog.
Chrissy
This is a really good post. It can be challenging to choose shoes to go with skirts. I don’t really feel comfortable in most heels and my arches are too weak for ballet flats, so that makes it extra challenging. I live in Florida so it’s really hot. I can get away with flip-flop type shoes as long as I’m not walking very far. I look forward to Fall though, so I can break out the boots!
Jacqueline
Shoes do pose a problem for so many of us. Funny, but I resort to flip-flops all too often, too! Boots are my staple in winter 🙂 Blessings, Chrissy!
Elizabeth
Another brand for people with foot issues: Vionic. I have a pair and I really love them. They are so comfy, and I have collapsed arches and plantar fasciitis.
Jacqueline
Thank you for that tip, Elizabeth! Once this juicing is over, I’ll be attending to my feet. Blessings!
Antonie
hi I saw you pics of clothing on Pinterest and I love them! Do I order from you? I especially like the long grey skirt, actually like so manyoutfits.
Please let me know how I can order them!
I live in Toronto, Canada.
Thank you,
Antonieta Minatel
Jacqueline
No, Antonie,
I don’t sell them. This is just a compilation of clothing that I like that shows how to wear shoes in a flattering way with skirts. Some of the photos have links, and if you follow them, you might find a company that is selling that specific outfit or skirt. Sorry I can’t be of more help! Blessings!
Julie
Have you shared thoughts about your changes in clothing choices?
Jacqueline
Hi, Julie! No, I haven’t written on it. It would be super boring 😀 It has always been a preference rather than a conviction and somewhat of a knee jerk reaction to my loose feminist days!
It has been a slow evolution from mild legalism/preference/deference to others around me to the grace we’ve been given in Christ! I firmly still believe we elevate ourselves as women by respecting our God-given bodies and not causing others to stumble.
Blessings to you! ~J