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How To Wear Ankle Boots Over 50

As the weather turns chilly and the ground gets messy, it’s time to stow our delicate footwear and embrace booties. They’re some of the comfiest footwear options for cooler weather because they’re stable around your ankle, which provides more support than a shoe. They also keep your feet warmer and dryer during nasty weather. Let’s look at some new ideas for how to wear ankle boots over 50. There are lots of new readers here, so I’m updating this post with fresh ideas and outfits.

PUFFER VEST / TURTLENECK / WIDE LEG JEANS / LUG SOLE BOOTIES / SLING BAG / EARRINGS

Booties are incredibly adaptable, and with a little creativity, you can work them into most outfits. Whether you prefer a rounded toe, pointed toe, short or long ankle shaft, block heel or stiletto heel, leather, suede, or fabric, there is an ankle boot for every woman’s needs. There are also plenty of flat boots with flexible soles and arch support in varying widths, so there’s no need to sacrifice comfort for style. 

Tips for Choosing the Right Ankle Boots Over 50

  • Comfort is key, so look for ankle boots with a comfortable fit, supportive sole, and a heel height that you can manage and walk in gracefully. Tottering around on sky-high heels that affect your gait just looks dumb. Plus, why risk your ankles?
  • Quality materials are an investment for the long term. Invest in ankle boots made from genuine leather or suede for durability and style. The new fabric options offer comfort and versatility for casual outfits.
  • Neutral-colored boots in black, brown, or tan are extremely versatile for your wardrobe, but don’t let that limit you.

How to Wear Ankle Boots with Bootcut, Flare & Wide-leg Jeans

woman wearing jeans, cashmere sweater and scarf

This is such a natural combination because you can skip the sock conundrum and simply cover the entire area. The hem of your jeans should cover the top of your foot and can extend partway down the heel to elongate your look and make your legs look longer.

How to Wear Ankle Boots with Straight-leg Jeans

OUTFIT DETAILS HERE

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 shaft or they’ll snag the top of the bootie when you sit down and need constant adjusting as you go about your day. The closer fitting the shaft, the better they work with straight-leg jeans. 

How to Wear Ankle Boots When You’re Petite

CHEETAH PULLOVER / SIMILAR BROOCH / SWEATER BLAZER / STRAIGHT LEG JEANS / LEATHER BELT

Proportion is critical when you’re petite, so wear booties that will allow your pants to cover the top of your foot and elongate your leg. The shorter the top or jacket, the longer your legs will look. Heeled booties will help you look taller, so if your feet can tolerate high heel booties, go for it.

How to Wear Ankle Boots with Leggings

fashion blogger jennifer of a well styled life wearing velvet leggings, blue sweater tunic and plaid scarf walking on sidewalk

Ankle boots with a higher shaft are great for tucking leggings into. There are no hard and fast rules, but the narrower your pant leg, the flatter your heel should be. When the boot and leggings closely match in tone or color, they give a long, lean line. For extra staying power, you can tuck the bottom of the legging into a pair of short socks, which helps to keep them tucked in. This look is great styled with a longer sweater, jacket, or tunic, which covers the top of the leggings and your backside.

You may also enjoy – The Modern Way To Wear Leggings After 50

How to Wear an Ankle Bootie with Skirts and Dresses

SOCK BOOTIES / TIGHTS / SIMILAR PLEATED SKIRT HERE, AND HERE / SIMILAR SWEATER / SHOULDER BAG

Knee boots are a classic look with skirts, but the latest trend of wearing ankle boots with skirts has become mainstream. You could pair it with bright-colored tights or go for the monochromatic look and match your tights to your ankle boots. Look for booties with a narrower and shorter shaft to help your legs look as long as possible. A pointed-toe bootie will also help elongate your legs and is a nice option with a midi skirt.

Types of Ankle Boots

Colorful Ankle Boots

EASY KNIT BLAZER / CASHMERE TEE / BOOTIES / JEANS / SHOULDER BAG / BRACELET

Black and brown boots are expected. Why not add a pop of color to a neutral outfit by pairing it with colored booties? I matched these to my blazer to keep the eye moving around my silhouette.

Style Tip- If your booties are the only pop of color in your outfit, all attention slams to a halt at your feet and stays there. Adding it in a scarf, blouse, hat, or jacket draws the eye back up to your face.

Flat Ankle Boots

OUTFIT DETAILS HERE

Skinny jeans are not as popular this year, but many ladies still love them, and they tend to look best with a flat ankle boot. Hem your blue jeans so that there is a small amount of leg showing between the skinny jeans and the top of the boot. Straight-leg jeans, pants, and trousers also work well with a flat boot when you have the leg long enough to cover the top of your foot.

Lug Sole Booties

navy easy spirit lug sole booties
EASY SPIRIT LUG SOLE BOOTIES

Lug sole booties look great with wide-leg pants and jeans because the wider leg adds visual weight, which helps balance the boot. They also look great with leggings tucked into them and a long, cozy sweater.

Sock Booties

EILEEN FISHER SOCK BOOTIES

Sock booties with a higher tight shaft are perfect to wear with a narrower leg because they’ll stay put and not interfere with the pants. They also work well with color-coordinated tights and skirts to give a continuous line that helps your legs look longer.

Embrace Elastic and Zippers

Booties with elastic side panels or zippers make it easy to slip them on and off with ease. I discovered knit booties in a stretch fabric several years ago and love their comfort. The heavier the texture, the more casual the vibe.

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.

41 Comments

  1. I love boots. They are so comfortable and stylish. Thanks for the super post.

  2. Super tips Jennifer; though I do admit because of the climate I’m in with long winters that deem boots, I avoid wearing them as much I can until necessary. -Brenda-
    P.S.: Added this post to my Style Pinterest Board.

    1. Thank you for adding it to your Pinterest board!

  3. Love all your outfits today; you look wonderful! I love boots and booties and enjoyed your tips on wearing them with different types of pants. I haven’t been able to embrace them with skirts, but maybe with your tips I’ll get up the courage to try! I ordered the Easy Spirit in the blue you showed. They looked wonderful with your jeans and most of mine are in the black and tan range so a color will be nice. Thank you! Love your blog!

  4. Great post, thanks for so many options with the pants or leggings or dresses. Always appreciate all the time you spend sending out the info. I love the boot season!

  5. Hey Jennifer! First time commenter! I love the booties that come up right at the ankle. I am also short. 4’11”. Should I have my pants above my ankles or to the top of the bootie. Most of the time the pant leg comes up over my bootie top when I sit, anyway. It really doesn’t look good. How is it supposed to be? I usually were cropped Jeans and Pants in the summer and full length in the fall and winter.

    1. Welcome! It depends on how wide the leg is but in general, a longer pant will make your legs look longer. Match your socks and boots to your pants for the longest look.

  6. Great post. You answered many of my questions !! I really enjoy your blog with its practical advice and choices from different stores. you have marvelous taste.

  7. Great post, Jennifer! I love my one pair of Taos ankle boots, but sadly they’ve developed an annoying squeak, so may need to check out some new ones! I have a question about wearing “fashion scarves” indoors, another blog I follow suggested this is a dated look. Wondering what you and other readers think about that?

    1. It depends on your style. Some women only wear scarves for warmth, others wear them to add a pop of color and brighten a look.I wear scarves inside if I’ve added it to a simple neckline for the purpose of styling rather than just wearing your clothes.

      1. Thank you, that is helpful!

  8. Thanks, Jennifer for such a great post about the booties! This answers so many questions about what colors,heel length,comfort etc. Very useful information!

  9. Great post today, very informative and a wide range of prices.

  10. I have never worn booties. I really would like to try a lug sole low heel bootie. I can’t wear Easy Spirit. They just don’t fit my feet. I live in Skechers as I have serious foot issues. I wear 6.5W in thin socks and 7W in my Smartwool winter socks. I need arch support in my shoes, no orthotics. I have to order online as I am very far from a city. Any suggestions to get me started with a pair would be appreciated.

    1. Do you ladies have any brand suggestions for Sydney?

    2. I purchase ABEO from The Walking Company, online now. They used to be in our mall. They have a few footbeds to select from online too. Enjoy!👍

      I also enjoyed this post, because I have various ankle boots in various colors but I didn’t pay attention to the shaft and they can only be worn with certain pants. That was not my goal. Thanks, Jennifer, I will be smarter next time thanks to you and your information👍

  11. I love all boots! I have some of every kind. I can’t really wear high heels anymore but I can wear wedge boots so I’m happy about that. Thanks for the great info!

  12. Elizabeth says:

    Like a few others I have purchased a couple of booties. I wore some last year with pants, and this year am trying to wear them with dresses. Thank you for mentioning that the shorter shaft(?) is better with dresses. My problem is that I wear colored tights depending upon my dress – mostly navy – and I think that the black booties just don’t ‘go’ with the colored tights – as if I am trying and failing badly. Of course, I can’t find booties in navy, much less other shoes. I mostly wear dresses (with pockets!) while teaching.

    With plantar fasciitis and flat feet, I found a great pair of Dr Scholl’s and also some Abeo boots. Trying to find a bargain – I have been able to successfully purchase the Abeo boots on Poshmark – barely worn.

    Thank you for helping boost my confidence in wearing this type of shoe. It is a change from my cowboy boots that my students love, as I am a Texan teaching in the Boston area.

  13. Love the wine tone bootie, all the looks are wonderful and inspiring. I need to check out my collection for this winter. Also looking forward to Nordstrom Rack opening in Pinole, hope soon, looks like work going on….Happy Thanksgiving to you and yours..

    1. A new Nordstrom is always fun!!

  14. Very helpful post! Up here in New England with cobbled streets, it’s helpful to have lug sole boots. It was great to see some that do not look like combat boots. Thanks for the tuck or not-to-tuck advice. Of course, as my ankle is broken, I’m envious of those who can buy new boots!

    1. I hope it heals quickly!

  15. I need sock booties! And love the red outfit.

  16. Try as I might, I just cannot adjust to the short boots with skirts. Other than that, I agree with and appreciate all of your recommendations! Thanks for a very timely post.

  17. If buying only one pair, would you suggest taupe or black for a lug sole ankle boot? Not sure which color would go with a variety of casual outfits…..

    1. Hmmm… it depends. If you want contrast and were a lot of dark pants, and I would choose taupe. If you don’t wear much black I would choose taupe. If you wear lots of black, brown, navy, then I would probably choose black.

  18. What boots are you wearing with the leggings? (sorry maybe I missed where you mentioned it)

  19. I have several pairs of Blondo waterproof booties. They’re perfect for winter, and I have them in taupe and black with low heels. They go with everything.

  20. Easy Spirit booties are great- comfortable, can accommodate my podiatrists insert forfurther arch support and try look good too! My go to with jeans or casual pants.
    (I really love your wine colored boot too! )

    1. These Navy booties are so comfy.

  21. This morning’s blog just stands out on several levels! So much useful information on just which bootie would work best with whatever we may be wearing. My first concern with any footwear is a secure fit that insures my confidence to walk on a variety of surfaces.
    Your choice of outfits today was just simply outstanding! Love them all! I can steal various elements of what you wore and update my style choices. I need this inspiration! Thank you!

    1. Thank you, Jan. I worked hard on this post, so I’m really happy to hear it is helpful.

  22. Thank you for this post! I LOVE boots and booties and just got my first two pair of the over the ankle boots for the wider leg jeans/pants and trying to work up my nerve to wear them with skirts, etc. Being mid 70s I kinda worry about trying to look too trendy or like the three (in their early 20s) grandgirls. This post is definitely a boost in that direction.

    1. I turned 70 this summer and decided that a top I had just purchased the month before was too young for me. It was my husband that changed my mind. He thought it looked nice on me and said “don’t put yourself in a box”. I wore that top several times and loved the fit and style. Let’s not allow turning 70 control our wardrobe. Let’s continue to follow the trends we like. Rock those ankle boots with a dress or skirt!

      1. Yay, I love this Joanna

  23. I got some nice Vionics for my trip to Rome! With how crazy our weather patterns have been, I feel like I’ve got myself somewhat covered, since they are water resistant! So if leave Minnesota in snow, I’m still ready for any rain in Europe! Thank you for your suggestions!!

  24. Great post, just what I needed. Thank you
    Kaarina P

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