How To Pick the Right Shoe

Happy Tuesday, ladies! Today I’m styling a sweater dress from Target, but I wanted to talk to you about how to pick the right shoe. It’s one of the mistakes a lot of women make when adding accessories to their outfit.

Here is where I think we make a mistake, we pick too dark of a shoe. I’m wearing a tan dress, so I want to keep my shoes light. These peep toe sandals are a brown sugar color and to be honest that is as dark as I want to go.

How To Pick the Right Shoe

Whether it’s a bootie, a sandal, a wedge, light is always a better option for elongating the leg. A lot of women will try to wear a black shoe because black is a classic. But black is also very stark, and it doesn’t always enhance your outfit.

How To Pick the Right Shoe

My rule of thumb is when, in doubt, always go light. I rarely wear a dark shoe unless it’s with dark pants or jeans.

How To Pick the Right Shoe

And while we’re talking about shoes, adding a heel even if it’s small, is always a good option. Heels also elongate your legs, especially when wearing a dress. In the summer, I wear a lot of sandals with casual dresses, but I prefer a heel with most of my dresses and pants.

How To Pick the Right ShoeHow To Pick the Right Shoe

This dress doesn’t have a lot of structure, so I think adding a denim jacket helps to add some structure to the outfit.

How To Pick the Right Shoe

Target Sweater Dress (I’m wearing a small)//Denim Jacket (I’m wearing a small)//Peep Toe Sandal (TTS)//Handbag//Bracelet//Bracelet//Earrings

Do you have a hard time picking out your shoes with your outfit? Was this helpful?

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Beauty For the Heart~~Lord, remind me how brief my time on earth will be. Remind me that my days are numbered—how fleeting my life is. You have made my life no longer than the width of my hand. My entire lifetime is just a moment to you; at best, each of us is but a breath. Psalm 39:4-6

I don’t have to read the above verses to know that life is short and time keeps flying by. I remember as a child thinking Christmas would never get here and now I feel like I blink my eyes and I’m pulling out the Christmas tree to decorate.

Our time here is brief, and we can get so busy that we forget to look for the blessings in each day. Don’t let today go by without seeing the blessings…the sunrise, a child’s smile, a hug from a friend, food on your table, the changing season. Today don’t miss the blessings!

Have a wonderful day!


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  1. VERY helpful! I’ve started wearing lighter shoes with most of my dresses, and I do think it updates the look a lot. Do you ever wear a black shoe with a dress these days? Only with a black dress?

  2. I love shoes, but I always wonder which to wear with what. I would love a whole post on shoes and outfits. I see a lot of booties with straight jeans, and I don’t know how I feel about that (perfect with bootcut jeans.)

  3. I enjoy your blog so much. My style is similar to yours and I gets some great ideas from you. Thank you so much for your daily “Beauty for the Heart”. It’s the most important thing in our lives.
    Shoes are my nemesis,,,,I love shoes, but have very narrow feet. I struggle to find shoes that are narrow enough. Do you have any thoughts on this fashion problem.
    Have a wonderful day.

  4. Great post as I often agonize about what shoe to wear! As someone with foot issues, I have to wear flats. I would LOVE it if you could show how to style outfits using flats, even when a heel is the obvious better choice.

  5. I love this dress with and without the jacket! Thinking that I will run out to Target today!
    And I totally agree with you on the shoes. I almost always go with nude and always a heel.
    Sharing this with some friends today. Thanks!

  6. Love your posts…I appreciate the tip about the shoe being lighter In Color than darker. Thanks. At this point in my life, I’m older and prefer a slight wedge or flats. But I try to find really pretty, fun flats. I love wearing booties in the fall/winter…but again a flat version.

    Thanks for sharing all your knowledge and the spiritual encouragements.

  7. I’ve noticed over the years how you often style an outfit with nude, taupe or tan shoes and now I’m noticing that my closet also has more of those shades of shoes as well 😉
    Unfortunately one pair are going back. The tan wedge sneakers with the side cutout from Nordstrom didn’t work out. They are a bit wide around my ankles and also squeak when I walked in them at home. I so wanted to love them.

  8. Absolutely love this whole outfit. When I looked up the dress though it has wool:( which I can’t wear so I will search for something similar. I usually gravitate towards lighter footwear, and this post helps to put it in perspective. Thank you for sharing this and oh that handbag!!! How cute.

    1. I also was wondering what’s the rule for a black dress? I’ve seen light neutrals and black.. whether the dress is just plain or has a floral pattern. Thoughts? Thanks

  9. What about in the winter? I tend to wear black tights and black boots/heels most days. I thought because the tights and shoes were the same color that it made my legs look longer. Is that not right?

  10. My question is pertaining to what to wear with jeans. I know which type of boots look good with jeans , but I don’t want to be wearing boots all the time. What type of shoe should I wear with jeans? I love a loafer type shoe but with jeans….maybe not. What do you think?

  11. Cindi. I have a question for you…I have a sequin royal purple dress & coat that I am planning to wear on our 50th Anniversary cruise and I can’t decide what shoes would look best with it. It’s length is just below the knee. Can you give me any suggestions? I can’t wear heels because of back issues so I’m limited in styles!! HELP!!!!!

    1. Gayle whatever you pick, it should be nude. If you’re asking what I would wear, I would wear a nude heel. That dressy of a dress probably needs a heel but if you can’t wear them go with a flat.
      No flip flop style shoe.

  12. Love this post with the shoe info!! Would you do another post with dark pants/jeans and show the best shoe option?

    Also, maybe consider doing a side by side comparison so we can see the actual difference in how the outfit looks?? One pic with the lighter shoe and one with a black shoe? The visual makes a huge difference!
    Thanks so much,

  13. Great info. I love my shoes. I would love for you to do a post on undergarments. For example, have problem finding the correct bra for something sleeveless like the dress you have on. Also bra that doesn’t cause back bulges.

    1. Have you checked out Soma? Their staff have so much knowledge and I love the vanishing back bra line. If I have an important outfit, I take it in with me so they can help fit me.

      (sorry Cyndi if I overstepped… blessings)

  14. I agree that neutral footwear is usually most flattering and that’s what I wear most of the time. I recently read or heard that one should pick a neutral shoe that is closest to one’s skin tone. I’m trying to pare down my wardrobe and update my shoes. Finding stylish, comfy, and affordable footwear is a challenge! It seems many of us have this issue.

  15. Cyndi, you are so cute, and you have beautiful words to remind us of what’s really important. Thank you!
    One fashion question: I seem to wear a lot of black and white. What shoes (sandals in summer) would you suggest with a black and white skirt and a black blouse or cardigan? I agree that black shoes/sandals can look a little stark on my white girl legs!

  16. Cyndi,

    I just love your blog! All the fashion advice is wonderful and your Christian insight is greatly appreciated! Keep up the good work; we love you!

  17. Agree 💯!! Shoes make or break an outfit. I have neutral ballet flats, sandals, booties, boots, etc. if I wear pants, I try to match my footwear to the pants. I’m 5’5”, so I try not to break up that long line.
    What do you think about metallic loafers and oxfords? I’m still seeing those this fall. Do you think they come across as neutral?

  18. It would be great to see how this outfit or a similar outfit would look with different shoes, especially with black shoes so everyone could actually see what you’re talking about here.

    1. Good idea and I also think it would be fun to see the outfit ideas that WORK and DONT WORK. LIKE— show it with some flats and black shoes so we can visualize. Great post, as always. Love this outfit!

  19. I can see HOW it can get confusing when picking out shoes for an outfit. When we click the link to the dress and are taken to the Target site…the model is WEARING BLACK SHOES!!! Plus a top beneath the sweater which I think is hideous! I much prefer your style!!!! Thank You!!!

  20. I loved this post! I always seem to have a problem picking the right shoe for the outfit. In fact, I bought the vegan suede dress in Caramel from Banana Republic recently, but I’m unsure as to what shoe to wear. Can you look at that dress & give me some pointers on shoes both style and color? Except for animal print, I’m not sure what to pair with it! I always enjoy your posts and your uplifting thoughts!

  21. Love your blog about shoes….You always look so good in a heel. But being a tall person, I can’t wear heels because I feel like a giant. What would you suggest with the sweater dress?

  22. I agree about lighter shoes and especially as I have gotten older! I am 5ft 2 in and have found dare shoes stand out to much on my short legs. Always enjoy you messages!❤️

  23. Cyndi,
    I’ve never had church in my life much when growing up. But as a mother I did raise my children with alittle more than what I had. I love reading your beauty of the heart, it lets me know what I am missing, and these verses are very inspirational to me.<3

  24. Yep yep yep! I’m always attracted to dark or black shoes in the store but I’m trying to change my ways. Good reminder because they do look great. Although.. I am looking for some black sneakers like you often wear with jeans. Might take a bit to make this transition!

  25. Great advice! The right shoe truly does make an outfit. I tend to feel exactly as you and prefer a nude shoe especially when wearing a dress with bare legs. With tights – only in the winter, I will wear dark shoes/boots; I too prefer a heel of some kind esp since I’m only 5’2” ;-).

  26. I love reading your Beauty For the 💜.
    I agree with your advice on the shoes, I’ve learned so many fashion tips from you, Thank you

    On another note, I will be attending an October wedding and need some advice on what to wear, especially since it will be fall. I have in mind a rust color or even an emerald. Your thoughts would be appreciated. 😊
    God bless you ⚓️🦋

  27. Great information. I have always heard your shoe should match your hair color. But that doesn’t always work. Dark hair, dark shoes…might not be best. Love The elongation hint!

  28. Yes, very helpful I have a lot of shoes so sometimes I get confused on which one…….I just stand in front of the mirror trying until one looks right. I did know that nude was good for elongation so have a lot of booties & dress shoes for church. I recently bought some pinkish nude booties that are Vince Camuto that were in a 5 in the store. Some times I can just have luck and sometimes not. Look forward to hearing more tips in Part 2.

    1. First off I just want to say Hi love you my sister in Christ. I have lots of shoes and I have 2or 3 or I gravitate to. Mostly light ones but always catch wear dark boots in winter. So I guess I am going ok picking out my shoes but if you are wearing dark colors, do you still wear light shoes? I just don’t like that look.