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    Flattering Shoes & Footwear To Wear With Skirts & Dresses

    9.7KViews Modified: Dec 20, 2022 · Published: Oct 24, 2012
    By Jacqueline 31 Comments

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    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.

    A Portrait Of Feminine Dress, Part 7 ~ Skirts and Flattering Shoes, strappy shoes, feminine, modest, with skirts, tights in the winter, leggings, flattering shoes for skirts

    (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!

    vintage sleeveless summer dress, modest, feminine

    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 🙂

     A Portrait Of Feminine Dress, Part 7 ~ Skirts and Flattering Shoes, strappy shoes, feminine, modest, with skirts, tights in the winter, leggings, flattering shoes for skirts, Linen Pantaloons in colour PISTACHIO, Susan Dashwood, New Verity Hope  (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

    A Portrait Of Feminine Dress, Part 7 ~ Skirts and Flattering Shoes, strappy shoes, feminine, modest, with skirts, tights in the winter, leggings, flattering shoes for skirts, nude pumps, neutral, pretty feminine dress with shoes, modest, feminine, how to wear

    A Portrait Of Feminine Dress, Part 7 ~ Skirts and Flattering Shoes, strappy shoes, feminine, modest, with skirts, tights in the winter, leggings, flattering shoes for skirts, nude pumps, neutral, pretty feminine dress with shoes, modest, feminine, how to wear

    (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.

    A Portrait Of Feminine Dress, Part 7 ~ Skirts and Flattering Shoes, strappy shoes, feminine, modest, with skirts, tights in the winter, leggings, flattering shoes for skirts, cute flats for wearing with skirt and dresses, purple shoes, feminine, modest

    (That Wife)

    Deck Shoes

    Canvas deck shoes are really perfect for this sporty cotton dress.

    A Portrait Of Feminine Dress, Part 7 ~ Skirts and Flattering Shoes, strappy shoes, feminine, modest, with skirts, tights in the winter, leggings, flattering shoes for skirts, deck shoes and striped cotton boat-neck dress, out on the lake,feminine dress, modest

     (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:

    A Portrait Of Feminine Dress, Part 7 ~ Skirts and Flattering Shoes, strappy shoes, feminine, modest, with skirts, tights in the winter, leggings, flattering shoes for skirts, deck shoes, polyvore of modest and feminine clothing with accessories

    Ballet Flats:

    ballet flats and slip-ons

    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.

    open toe

    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)!

    warm footwear

     (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.ski sweater(Source)

    women in boat

    (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.

     Flat, feminine, quality comfort shoe

    ~Merrell is an excellent shoe and has a whole line for everyday and for outdoors and active-wear:

    flattering shoes for skirts

    ~Keen for daily wear and active wear, too:

    Keen brown support shoe

    The simple Mary Jane by Crocs. Very comfortable.

      Mary janes

    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

    Finding Flattering Shoes & Footwear To Wear With Skirts & Dresses. strappy shoes, feminine, modest, with skirts, tights in the winter, leggings, flattering shoes for skirts

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    Hi! I’m Jacqueline!

    Thanks for being part of this journey with me.
    Welcome to my own little place on the internet! Home is where I love to be. I feel there is no greater place to incubate souls. These days you’ll find me using my experiences here to write about herbal remedies and natural health research — a big passion of mine. But being a wife and mother is not easy. It is challenging and potentially lonely. I get that. I wanted to create a place to connect with and support other moms for creating a natural, healthy, and fulfilling home life.
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