BOOTS THAT LOOK BETTER WITH A DRESS

Ankle boots with a knee dress worn by Fashion Blogger 50 Is Not Old I have been busy for the past few days, purging and cleaning. You can tell that I am a collector at heart, so I have a hard time letting go of things. I can always think of reasons that I might use the item in the future. However, how many sheet sets do you need for each bed. I believe the correct answer would be two. That way, you could wash one and have one on the bed. The same goes for towels; how many do you really need? This is the giveaway pile from one linen closet! Isn’t this crazy? The cabinet is still full; you can see the towels now. Lol!
Knee boots with a plaid dress worn by Fashion Blogger 50 Is Not OldBecause I have been so busy cleaning, I haven’t been taking pictures. So, I am improvising instead, and I think that you are going to like the results. I thought about what you have mentioned in the past, and how to wear boots with dresses was one of the top requested topics. There are tons of boots that you can wear, such as knee boots, ankle boots, combat boots, cowboy boots, and they can have all kinds of heels.

Each of the photos is from a prior blog post. I have linked them to the post. So, all you have to do is click on the photo to be taken to the post. You can read the post and see the links to the items in the post. At the end of this post will also be a photo of different boots. All you have to do is click on the photo to be taken to the boot that you like.
Black over the knee boots with a red sweater dress worn by Fashion Blogger 50 Is Not Old These boots are an Over The Knee Boot, and they look great with a shorter dress. This particular sweater dress hits right at the knee, and with these boots, you don’t have to worry about wearing tights or your white legs showing. Lol!
Gray knee boots with a pintucked dress worn by Fashion Blogger 50 Is Not OldI like having some skin showing when I wear boots with a dress. Adding these gray knee boots to my pintuck dress gives some visual interest and breaks up the photo. I also think that this is a more youthful look, but it doesn’t look too young for women our age. Is this a style that you can see yourself wearing?
Knee boots with a swing dress and a denim jacket worn by Fashion Blogger 50 Is Not OldThis outfit was one of a 5 part series on how to take a dress and style it several different ways. Click on the photo to be taken to this look, and then you can look at the other looks if you are interested. This is one of my all-time favorite looks for wearing a dress with a knee boot. I like the boho, casual vibe of the look that the boots, jacket, and belt bring to the look. These knee boots have a chunky heel and a gorgeous caramel color.
Open toe boots with a floral maxi dress worn by Fashion Blogger 50 Is Not OldI wanted to make sure that I included a maxi dress and also an open-toe bootie. How lucky for me that I found both of these items in one post??? I love wearing a maxi dress in the summer and early fall, and adding the open-toe booties are great with this look. I quit wearing my open-toed boots once the weather gets cold, but I love them for the rest of the year.
Black knee boots with a red pencil skirt and a gray poncho worn by Fashion Blogger 50 Is Not OldKnee boots or Over The Knee Boots look great with a pencil skirt. Maybe it is just me, but I love the effect that they give off in this look. This is another one of my favorite outfits from back in 2018, and you won’t believe where I bought the poncho. Remember, click on any of the photos to be taken to the blog post.
Vince Camuto over the knee boots with a navy pencil skirt and denim jacket worn by Fashion Blogger 50 Is Not Old Here is another example of a pencil skirt and a pair of over the knee boots. These boots are relatively new, and I am pretty sure that I have them linked below. They are a favorite of mine, and I think they are on sale.

Here are some of my favorite boots. You can click on the photo of the boot you like to be taken straight to the link. Every one of these boots is on sale, so be aware that some of them may have limited sizes. Also, many of these boots come in other colors, so if you don’t like black but like the style, you can click on the photo and check out if it comes in other colors. I am pretty sure that every boot is under 100.00, and there are some under 30.00. I ordered several for myself because they are such a great buy.


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  1. Oh I like that maxi dress a lot! I love to wear my boots and I always wear dresses with boots in Winter!

    Posted 1.13.20 Reply
    • Tania wrote:

      Boots with a dress or skirt is one of my favorite looks in the winter months.

      Posted 1.13.20 Reply
  2. Ava Nickerson wrote:

    Great outfits! Your blog is always fun to read when I get to my computer.

    Posted 1.13.20 Reply
    • Tania wrote:

      I am glad that you enjoy it Ava!

      Posted 1.13.20 Reply
  3. Jaymie Ashcraft wrote:

    Great looks! I love boots and dresses together! It’s my favorite way to wear a dress!
    Jaymie
    http://www.jaymieashcraft.com

    Posted 1.13.20 Reply
    • Tania wrote:

      I know, Jaymie! I love wearing boots with a dress.

      Posted 1.13.20 Reply
  4. Becky Sanchez wrote:

    Hi Tania!
    I love this post! These outfits are so cute!
    Any updates on Thomas? I’ve been praying you guys will be able to catch him.

    Posted 1.13.20 Reply
    • Tania wrote:

      Oh, Becky, you must have missed my post. We found Thomas!!! He is back safe and sound. My daughter is planning on taking him back to Alaska with her later this week.

      Posted 1.13.20 Reply
  5. Cheryl peffer wrote:

    Boots are so fun. Years ago I purged , amazing how much stuff you keep. As for towels and blankets I have them to the Humane Society. They were glad to have them. As for the rest of the stuff it mostly went in the trash. Lol.

    Posted 1.13.20 Reply
    • Tania wrote:

      Cheryl, it makes such a horrible mess during the process. I have already contacted my humane society.

      Posted 1.13.20 Reply
  6. I love wearing boots with dresses. They add such sass! Plus if I”m wearing tights I find I can wear a shorter dress than I normally would. Dresses fit my shape really well (apple shape) so I’ve got every boot imaginable!

    Posted 1.13.20 Reply
    • Tania wrote:

      Hahaha! I like adding sass!

      Posted 1.13.20 Reply
  7. Wendy wrote:

    Great ideas for boot combinations…and thanks for the daily fashion inspiration!! You make us feel fashion can be fun at all ages♥️

    Posted 1.13.20 Reply
    • Tania wrote:

      Wendy, I am so glad that you liked the post.

      Posted 1.13.20 Reply
  8. Justine wrote:

    I so can relate to your pain in keeping items!! I keep things because I’m sure I will need them for something and then I finally part with said item and sure enough I need it! Lol thanks for your dedication and I really enjoy your posts.

    Posted 1.13.20 Reply
    • Tania wrote:

      That is how I am too, Justine. As soon as I get rid of something, I will find myself searching for it. LOL!

      Posted 1.13.20 Reply
  9. Anne wrote:

    Thanks for this post!! You look beautiful!! It helps me to be inspired to put more effort into choosing an attractive outfit!! Joe is lucky to have found you! You are beautiful and funny too!!

    Posted 1.13.20 Reply
    • Tania wrote:

      Oh, Anne, I HAVE got to read him your comment. Lol!

      Posted 1.13.20 Reply
  10. Julia wrote:

    Tania, I love your blog! This is a great post with lots of different ideas. You look beautiful in each of these pictures. Thank you for inspiring women in their 50’s and beyond to look their best.

    Posted 1.13.20 Reply
    • Tania wrote:

      Julia, that is very sweet of you to say.

      Posted 1.13.20 Reply
  11. Fleurette Wollter wrote:

    My husband bought me a pair of black and silver cowboy boots. I wasn’t sure how to wear them. I was browsing my closet and I found a royal blue mid-length dress. I paired the boots, the dress and a black and silver (narrow) belt, (I’m only 5′ tall). I received so many complements! I am 65 and I really thought this might be pushing it a bit, but this outfit makes me feel soooo pretty.

    Posted 1.13.20 Reply
    • Tania wrote:

      That sounds amazing. Cowboy boots are one of the few types of boots that I don’t wear.

      Posted 1.13.20 Reply
  12. Monica Ercanbrack wrote:

    Love the post I also have trouble getting rid of stuff (in case I might need it) lol.
    My favorite is the turquoise outfit.

    Posted 1.13.20 Reply
    • Tania wrote:

      I know. I am sure that I will need it in the future. Lol!

      Posted 1.13.20 Reply
  13. Ellibelle wrote:

    These are all such great looks! Especially loving the royal blue dress!

    Posted 1.13.20 Reply
    • Tania wrote:

      It sounds like the royal blue dress is a winner!

      Posted 1.13.20 Reply
  14. Becky wrote:

    Oh! I love fairy tale endings!! I don’t know how I missed it! He’s a gorgeous boy! I’m so glad!!!

    Posted 1.13.20 Reply
  15. evegpt wrote:

    I just gave my last boots to my neice. Wobbly ugly knees and lack of energy to pull those boots up and take them off makes me want to just slip on an easy shoe. Loafers and flats are my standbys but there was a time when denim skirts and high red boots were my love. Some things are best left to those under 75! LOL. I still love posts like this and I do still wear booties. I love those.
    Mama told me you only need three of everything when I complained about not enough clothes. One .you are wearing. One in the laundry and one in the closet.

    Posted 1.13.20 Reply
  16. Lori wrote:

    Thank you for such a wonderful job of giving so many different options with boots. Your pics looked great!
    I have a question though about jeans…..and just where to look for great fitting jeans without the extremely high price tag. I don’t mind paying more for good denim but the prices can get really high.

    Posted 1.13.20 Reply
  17. Connie J wrote:

    I love the looks you posted today. I have tons of boots and get stuck in a rut sometimes about what to wear them with. Thanks for the style inspiration.
    I purged my linen closet last year but need to work on my actual closets some more. I donated a ton of stuff to our local thrift store but need to take them some more.

    Posted 1.13.20 Reply
  18. KRISTIN GREENE wrote:

    This post was great. I loved seeing different ways to pair boots with an outfit.

    Posted 1.14.20 Reply
  19. Leslie wrote:

    Thank you for your post. I pinned several of your photo’s. You always look stunning! You gave me some great idea’s. Many thanks!

    Posted 1.15.20 Reply
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