How To Wear Ankle Boots Over 50

How To Wear Ankle Boots Over 50

It’s bootie season and I couldn’t be happier. Ankle boots are some of our comfiest footwear options for cooler weather. They’re stable around your ankle which provides more support than a shoe and will keep your feet warmer and dryer during nasty weather. There are plenty of flat and low heeled versions with flexible soles so there’s no need to sacrifice comfort for style with booties.

I’ve shared how long your pants should be here. Today I’m sharing five ways to wear booties over 50 and the right pant length for each.

With Leggings

Ankle boots with a higher shaft (higher on your ankle) are great for tucking your leggings into. It gives a long lean line when the boot and leggings closely match in tone or color. For extra staying power, you can tuck the bottom of the legging into a pair of short socks first. This look is great styled with a longer sweater, jacket or tunic which covers the top of the leggings and your backside. If you’re a workout instructor, you may be able to wear leggings with a short jacket, but those days are long gone for me;)

With Skinny Jeans

Tucking skinny jeans into ankle boots isn’t usually effective because they come untucked as you sit and move around. Skinny jeans are also notorious for bunching against the top of ankle boots which makes your legs look shorter. Here are two solutions-

  • cuff them up to have 1/2″ of ankle between the boot and your ankle. You can fold over twice to have a narrow cuff or one large fold. Be aware, the wider the cuff, the shorter your legs will look. If you cuff your jeans, wear a shorter top to help elongate the look of your legs.
  • You can also simply hem your jeans which I prefer for my short self.

With Straight Jeans

Straight jeans look great worn over the top of the ankle boot. Be sure your jeans are long enough to cover several inches at the top of your ankle boot. This works best with ankle boots that have a narrow opening on top.

With Cropped Jeans

These are a great option to wear with ankle boots because it leaves a little leg showing between the ankle boot and hemline. Just be sure they aren’t so cropped that you have 5 inches of shin showing.

With Bootcut Jeans

This is the easiest of all. Make sure your jeans reach the top of your arch. You can also hem them longer than usual to cover a small heel which elongates the look of your leg.


Booties also look great worn with a skirt or dress. The height of your ankle boot matters here. You want the maximum amount of leg to show so in general, choose a low cut bootie. Another great look is to bridge the gap with tights the same color as the bootie which helps make your legs look longer. Maxi dresses look fabulous with ankle booties. Choose a bootie with a narrow top so the skirt doesn’t get caught on it.

Lower Shaft Booties

The crop of booties this year is extensive so there’s plenty of options to chose from.

Are you a fan of booties?

How do you like to wear yours?


Thanks for reading and be sure to wear what makes you feel confident.

This post may contain affiliate links which won’t change your price but will share some commission.


  1. Sandra McDonald
    November 6, 2019 / 5:17 pm

    Please share a link to the snakeskin booties that you are wearing in the first photo.

  2. Ellen
    October 31, 2019 / 9:05 am

    Good post! Being pear shaped, I find showing skin above the boot to really shorten my leg line…not a good look. Also really struggle with booties and dresses. I think it looks cute on women with slender, well shaped legs and ankles but it just doens’t seem flattering with my thicker ankles. Love them with boot cut and straight leg!

  3. Nancy D
    October 30, 2019 / 11:47 am

    I love my short boots with leggings as well as straight leg or skinny jeans. My eyes simply cannot adjust to seeing short boots with cropped pants or with skirts.

  4. Kay
    October 30, 2019 / 10:58 am

    I read the title as wearing my 50 year old boots! I had a pair in high school I wish I had kept. Brown patent leather. I loved them. I find the ankle length pants work best for me with boots.

  5. October 30, 2019 / 10:05 am

    Great advice! I love ankle boots and wear them with just about everything!!

  6. jmp
    October 30, 2019 / 8:22 am

    This is just the information I needed! Thank you

  7. Griselle Camacho-Claudio
    October 30, 2019 / 8:18 am

    They are my go to from fall until the cold weather is gone. As you stated they are very comfortable and I like to wear them with socks as long as they don’t show. I have dressier ones with heels for special occasions and I have 4 pairs of Blondo booties in Natural, Black, Tan and Grey. They are wonderful and waterproof. I don’t need to worry if it is going to rain or snow here in Pennsylvania with those boots you look well put together and don’t need to worry about the weather.

    • October 30, 2019 / 2:58 pm

      I have my eye on a Blondo bootie right now. They really are fantastic.

      • Lorna
        February 4, 2020 / 11:49 am

        I love Blondo booties, but the heel is too high for me at 3″- 3 1/2″. I wish they made them with 1″-2″heels, as they are so beautiful! If they did, I’d buy them in multiple colors!

  8. Vanessa
    October 30, 2019 / 7:39 am

    Love this post! Love booties

  9. Joanna
    October 30, 2019 / 7:38 am

    I love booties! I have several pairs in different styles, heights, and colour. They are my favourite fall, winter & early spring footwear of choice.
    I agree on the bunched skinny looking wrong. It’s much better to cuff. I prefer a small cuff versus a wide one.
    As for wearing with dresses, I think a more feminine boot is required. I like the look with midis.

    • October 30, 2019 / 2:56 pm

      I feel the same. My legs are just too short to accommodate a wide cuff.

  10. MRSBEN2
    October 30, 2019 / 6:23 am

    Excellent advice, Jennifer. As for myself and lower cut boots with pants I much prefer no leg showing when one is seated so often wear color coordinated knee-high hosiery with mine either to match the shoe or bottoms. Also for those who do not like the look of a cuff; double-sided cello tape (applied to the inside) is an easy fix for temporary shortening of a pant leg. -Brenda-
    P.S.: I wear my ankle boots mostly with skinny leg jeans/leggings and/or pants whereas prefer longer style of boots with skirts/dresses in varying hem lengths.

    • October 30, 2019 / 2:55 pm

      Great tip Brenda. I’ve been known to just iron mine under for a one-time usage too.

    • Mary F
      November 2, 2019 / 5:10 pm

      Mrs Ben, I agree with you, although we seem to be in the minority. I just do not care for the look of bare skin between pants and shoes in the winter. I also do not like the feel of booties rubbing on bare skin at their tops. So I also wear socks or knee-highs, even though it is, apparently, a fashion faux pas.

  11. October 30, 2019 / 5:01 am

    Thanks so much for this helpful post! I was just starting to wear my first pair of booties and trying to figure out how they work with various pant lengths and which socks. Then we had a heat wave in the 90’s and I went back to sling backs and no socks 🙂

    I hope the air is good where you are. We had to evacuate from Santa Rosa. Packing objects was easy…you go for irreplaceable. Clothing was the opposite. Take the most practical for the next few days and leave everything else behind. Sounds so superficial in the midst of disaster. Hopefully they will get the fires contained soon. I hope you and your family are far away from this!

    • Catherine Vanderpool
      October 30, 2019 / 8:51 am

      Be safe and thanks for sharing.

    • October 30, 2019 / 2:54 pm

      Oh no, Marian. That’s so awful. I hope your home survives this fire. I never remember fires being so bad in the past.

  12. Audrey Storms
    October 30, 2019 / 4:35 am

    I enjoy my booties. I have two pairs in different colors. As a petite I wear them with dresses and different style jeans.

  13. October 30, 2019 / 4:12 am

    I love my boogies and wear with leggings at times, but mostly with straight length dark wash jeans. As you say, they are comfy, secure, and really look great I think. I have two pair as well.

  14. sheryl
    October 30, 2019 / 3:42 am

    i love my two pair of shoe boots, i have cognac and black, and they are enough for south florida winters. i prefer to wear them with just jeans…skinny straights with a tunic or blazer, or bootcuts with anything else.

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