50 IS NOT OLD | HOW TO STYLE BOOTS WITH A DRESS | FASHION OVER 40Let’s face it, when it comes to the fall and winter season, boots are going to be the shoes of choice. I love boots and I have them in all different colors. Plus, I have them in several different styles including open-toe, military, ankle, and over-the-knee. The area that I have struggled in when it came to wearing boots was how to wear them with a dress. There are just some occasions when only a dress will do and the right style of boots can really make the difference. In the picture above I have paired a pair of black pointed-toe ankle boots with a pair of textured tights. 
50 IS NOT OLD | HOW TO STYLE BOOTS WITH A DRESS | FASHION OVER 40But, with this maroon sweater and skirt combo, I went with a pair of brown block heeled knee boots. The skirt is a midi and the length of the skirt called for the higher boot. If I had worn an ankle boot with this look it would have made my legs look like stubs. Instead, the solid color scheme made me look taller and that is usually a good thing.50 IS NOT OLD | HOW TO STYLE BOOTS WITH A DRESS | FASHION OVER 40 This black sweater dress hit me right at the knee level. With this look, I decided to wear the same ankle boots that I have on in the first picture, but with a pair of sheer black hose instead. The sheer hose makes the look more elegant which was what I was looking for with this look. 50 IS NOT OLD | HOW TO STYLE BOOTS WITH A DRESS | FASHION OVER 40In this look, I opt’ed to wear a pair of knee boots with a shorter dress that hit me well above the knee. Yes, I could have used a tan but the boots were cute. Lol! I was hoping that everyone would notice the boots and forget all about my “ghostly” white legs. I could have just said that I was going as a ghost for Halloween and I was getting in costume. Hahaha!50 IS NOT OLD | HOW TO STYLE BOOTS WITH A DRESS | FASHION OVER 40 This is a pair of over-the-knee boots by Tommy Hilfiger. I love this pair for the color and also because of the low heel. I decided to wear them with a striped sweater dress and cardigan that just meets the top of the boots. How many of you own a pair of over-the-knee boots? How do you wear yours?50 IS NOT OLD | HOW TO STYLE BOOTS WITH A DRESS | FASHION OVER 40 Here is another look at a shorter dress and a pair of knee boots. I am not sure if it is the length of the dresses or the style of the dresses, but I think I look younger in those photos. Is that my imagination? I am not talking “face” when I say younger, I am talking the overall effect. 50 IS NOT OLD | HOW TO STYLE BOOTS WITH A DRESS | FASHION OVER 40And, the last example for today is a dress and a pair of solid colored tights with a pair of suede ankle boots. Tights are very popular right now but I have not yet jumped on board the trend. What do you gurls think? Are you a fan of tights?

I know that today’s post is different from most of my posts. Joe and I both had a set back with our colds and if you could have seen me yesterday you probably would never follow me again. Lol! I didn’t get out of my pj’s all day long and I slept at least 3/4 of the day. I would wake up and eat and then go and lay back down. If I don’t feel better by today I am going to have to break down and go to the doctor. I have a birthday party to attend this weekend in Tennessee and I want to be feeling better to play with my grandchildren. Send me some good vibes, I need them. Plus, some chicken soup would be nice too. Lol!!!

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43 Comments

  1. Aimee Spencer Reply

    I will be the first one to send you get well wishes today ! Yes the chicken soup is highly recommended by my granddaughter’s doctor. For kids as well as adults. It’s the chicken broth as well as the vegetables that your body needs. Your doctor may prescribe something if you have a fever. I also suggest getting over the counter Afrin that is a liquid and you squeeze drops in your nose. It works like a miracle. I sure hope you guys feel better soon.😊

    • Tania Reply

      Aimee, I wanted to make chicken soup yesterday but just couldn’t make myself get up off the couch and go to the store 🙁 I am going to do that today and I will look for the Afrin. Thanks for the recommendation!

    • maggi ostrowicki Reply

      Tania, you have such a great sense of style and your closet must be fabulous. Keep them coming. I get a lot of ideas from your pics….

  2. Firstly let me say “get well soon”. Secondly I love the dress with the coloured tights and boots, this has got to be my favourite. Can you tell me more about the dress, please?

    • Tania Reply

      I am not sure which one you are talking about, Jill. If it is the last one, that is a dress from an online shop called Eva Trends.

  3. It is really helpful to see various ways to wear boots with dresses. I struggle with this. Tights are a must in Canada or you will freeze, so I am a fan. I often wear tights and tall boots just for warmth. When it is really cold I don’t wear dresses at all. I think the dress length and mostly the denim jacket make you look younger. I see that myself when I wear that combo. Feel better soon! One of the things I dislike the most about this weather is the colds that come with it. I don’t have time to feel lousy!

    • Tania Reply

      Thanks, Janet. I didn’t know you lived in Canada. Lol!!!

  4. Hope your are feeling better sweet friend! Yes, I like tights with some dresses. I think it depends on the type dress. I am loving the striped ruffle dress with the knee boots. Rockin’ it as always!

    • Tania Reply

      Thanks, Susanne. I can’t believe you got some snow this morning. What?!?!?!

  5. Sounds like you had a bit of the flu. I’m sending you both well wishes. I wear tights with dresses as soon as the weather gets cold. I loved the synopsis of dresses and boots. Very helpful! Feel better soon friend!

  6. So sorry your cold is hanging around. Prayers for a full recovery.

    You look great in all of the pics, but I love the teal dress with the boots and denim jacket on you. Yes, you do look very young!😊

    Feel better soon.😊

    • Tania Reply

      It makes me want to recreate that look with a small twist. I’ll have to see what I can do.

  7. Yes you do look young in the blue short dress with boots! Very good post with different dress and boot options.

  8. Prayers for you both to feel better soon. Rest is needed to heal. Something that is hard to do. Finally cooler weather in Savannah! I enjoy my lower heels boots with pants almost daily. Good to see all your outfits suggestion. Take care of yourself.

  9. I am a big fan of tights and I really like the textured pair. Not only are they comfy, but oh so warming! I love all these oufits, but my favorites are the 2,3 and 6! You can NEVER go wrong with black, the color in that cardigan is amazing and that denim outfit is so nice with the large belt!!! All the boots are great too!
    Sending good vibes that you both are feeling better. You definitely should go to the doctor if this doesn’t clear up, you don’t want this to turn into something worse. Always be on the safe side. It’s important to stay healthy at our age!! Be well!! 😊😊

    • Tania Reply

      My mom has a saying about erring on the safe side. I need to remember that!

  10. Everyone at work has had this virus and it takes 2weeks to fully recover. Hope you are feeling better soon. I love tights and fleece lined ones are the best in the dead of winter. I am not a fan of over the knee boots but do love colored booties! Best…Kathy

    • Tania Reply

      Joe is going on 3 weeks now and I am going on 2 weeks so we should be over the worst of it. My Energizer Bunny Friend got it before Joe and she is still not feeling good. It must be one that is like glue…..you just can’t get rid of it.

  11. Hope your cold is better! You looked great in all the pics but I didn’t love the last one. All of that voluminous floral fabric seemed too much for your small body.

  12. So sorry you can’t kick this cold! Chicken soup can help!

    Really like the ideas of boots with different outfits! I sometimes wonder if these boots are “right” with my outfits and your examples really help! I am 71 and don’t want to dress “old” but not a “teenie bopper” either! I guess I like to dress edgy but appropriate! Thank you for your blogs!

  13. What is your advice on what style of jeans to wear at our age? I struggle to know which cut goes with which show style. Thanks

  14. ❤️ your 4th and 6th pictures! You’re adorable! Hope you have a fabulous week! 😘

  15. Cheryl peffer Reply

    I never got on board with the tights. Looks good on everyone else. Feel better.

  16. I think this was good idea for a post because I have trouble with wearing ankle boots with dresses. I like the look but when I put on I feel funny. But you’ve shown what type dress looks best with booties and with knee high boots. Thanks. I’m taking your advice. And the photo of you in short blue dress with denim jacket made me think of your inner cowgirl. Cute. Cute. And you do look younger in shorter dress. Longer ones make anyone seem more mature. And sometimes that’s called for. You look great in them all.

  17. I forgot to say that the black cape in picture 3 is gorgeous. Very dramatic.

  18. Cheryl Wilcutt Reply

    I love that you wear dresses that hit at or above the knee! These are all great options, thanks for sharing!

  19. Picture #6 is adorable. You should wear those shades of teal/turquoise more often! And I dearly hope you feel better soon, Tania….or go to doc if need be to speed up your recovery. Sending good wishes to you. Take care!

  20. Cindy Arnold Reply

    I hope that you feel better soon. I love boots with dresses, and I’m short so it is a constant struggle. I like the tights idea, maybe it could make my legs appear longer. 🤔 I also love wearing a Jean jacket! It makes me feel younger too!! Have a great day. 😍

  21. Luv the black elegance and the jean jacket outfit. Stylin’! Yes, the Jean jacket outfit offers a younger look. However, you look fabulous at any age!

    • Tania Reply

      Regina, I am thrilled for you to get started. Use a very SMALL amount of product. I wipe off the brush on 2 or 3 of the sides and only apply that tiny amount to my lash line. If you apply too much of the product it can “move” into your eye and you will get red eyes. Then, be patient. Some ladies see immediate results and some are like me and take 12 weeks. I look forward to seeing your results.

  22. I love wearing tights because I am NOT a legging person. There are so many into leggings and I just feel like when I’m wearing them I’m still bare from the waist down. And…you can get fleece lined tights that are oh so warm in the winter with boots. I’m interested in finding out more about the very first dress. Is it still available someplace? Feel better. I had that bug last year and it lasted over a month and did have to end up going to the Dr. This year I got a flu shot for the first time so we will see if that makes a difference or not on how long it lasts “if” I do get it.

    • Tania Reply

      Leggings or tights are basically the same for me. I don’t wear socks normally so for me to wear tights is different. The dress actually came from Target last year so I doubt you will still find it anywhere. I am feeling better today so maybe all of the rest yesterday was what I was needing.

  23. Thank you for this post. I have struggled with how to wear. Booties, tights, hose and dresses in the winter and still look modern. Thank you.

  24. Love the boho dress and short teal one. I love dresses year round-I find tights to be just as warm as jeans. I’ll even wear leggings under a casual style dress. Abercrombie has some great knit ones typically that look great with leggings. I love my OTK boots, they are taller than yours and actually come all the way over my knees. Dresses or leggings or super skinny jeans is how I wear them.
    I’ve had the “crud” for a full 2 weeks and just now starting to feel better. I don’t do doctors unless I think it might be strep, bronchitis, or a sinus infection. Everything else is probably a virus that just has to run its course. Hang in there.

  25. Jayne Finkbohner Reply

    Absolutely love each outfit. Truly love the tight with dress. So darn cute. Feel the same way as you but it is a trend that is growing on me as well!!
    Hope your feeling better.

  26. Awesome to show several outfits to give examples of a look.

    Luv the video tutorials!!!
    Make up ,packing, hair style

    Cynthia
    St.Augustine Fl

  27. Lisa Melton Williams Reply

    You definitely rock that jean jacket outfit and yes it does make you look very young! It’s adorable!

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