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How To Wear Ankle Boots Over 50

It’s bootie season, and I couldn’t be happier. I find them one 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. There are plenty of flat and low heeled ankle boots with flexible soles, arch support, and available in varying widths so there’s no need to sacrifice comfort for style with ankle boots. Today, I’m updating this post from 2019, with some new ideas for how to wear ankle boots over 50.

With leggings

over 50 fashion blogger jennifer Connolly wearing talbots Ribknit poncho in Blackwatch Plaid
WEARING – similar ANKLE BOOTS  – CHAMBRAY SHIRT  similarSOHO PONTE LEGGINGS – PONCHO sold out

This year’s version of my above booties is available in Medium, Wide, Extra Wide, Super Slim, and Narrow widths. Yes, they’re an investment but mine has paid off year after year because they fit my wide foot and are incredibly comfortable. 

Ankle boots with a higher shaft are great for tucking 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 which helps to keeps 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.

Related- The Modern Way To Wear Leggings After 50

With Skinny Jeansgray suede booties and jeans

Tucking skinny jeans into ankle boots doesn’t work well because they come untucked the minute you sit or 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-

  • roll up and leave 1/2″ of ankle between the boot and your pant. 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.

Skinny jeans look best with some ankle showing so cut-out or split-shaft booties like these are a great option.

Related –How to Shorten Your Jeans and Keep the Original Hem

With Straight Jeans or pantsover 50 fashion blogger jennifer conolly of a well styled life wearing black and red checked pants and black sweater

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 close-fitting top.

With Bootcut Jeans

woman standing near railing wearing fall outfit
WEARING – SWEATER -runs large –  WHITE SHIRTBOOTCUT JEANSANKLE BOOTS

The perfect combination. Have your jeans reach the top of your arch or you can hem them longer than usual to cover a small heel which will help elongate the look of your leg.

ankle boots with width options

Related –How to Look Taller and Slimmer

The selection of booties this year is extensive so there are plenty of options to choose from at all price points.

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.

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48 Comments

  1. I really enjoy all my boots short, tall, in between and booties.
    They just add class to any outfit.
    Thanks for the great information. 😊

  2. I love your outfits. I have several types of boots. Some ankle height and some calf height. In the winter I struggle with not wearing socks. My ankles get very cold here in the North East. But I do like the look when there’s some skin showing between your pants and your booties. Do you have any recommendations on how to keep your ankles warm in the winter time?!

  3. My son’s girlfriend visited Boston for Xmas several years ago. It was REALLY cold. She did the 1″ gap between booties and leggings. When we stopped for coffee and cannoli, she had a bright red band of frozen skin around her ankles! Fashion met mother nature,and mother nature won. I love booties, BTW but wear mine with full length pants or with leggins tucked into socks. Going to try a split look this year. Great post.

  4. I LOVE LOVE LOVE all my booties! Boots in general. From UGGs to over the knee boots. I have so many that I can’t count them all!! My husband was forced to retire during COVID and now we’re moving south from Boston in the summer. I’ll be the only 1 in FL or GA wearing boots. Lol!

  5. Great post and styling tips! I have always loved boots; in all styles. Last year I discovered the split shaft idea and bought several pairs in different colors. They are so easy just to slip into andIt has to be a low heel for me. I have lots of suede booties as well as some open toe leather ones that I can still wear in our warm October weather.
    I wear booties with skinny jeans and leggings all winter long. I just bought a pair of beautiful burgundy suede booties and can’t wait to wear them, although I dropped my laptop on my (bare)foot last week and all I’m wearing are slippers! Lol! It’s not bootie weather here yet, so I have a little reprieve!
    Enjoy your weekend Jennifer!

  6. The weather turned cool enough for booties recently and I loved getting mine out to wear again. My legs aren’t the shapeliest so I struggle with wearing booties and tights with dresses… not the best look on me. I just bought a pair of almost knee high faux suede boots to wear with dresses instead. How do you feel about tall boots, Jennifer? Are they on trend?

    1. I love them, Ann!! They are my first choice with skirts of any length. I need to get mine out when I get home from this trip.

  7. I love boots as l feel taller (being 5”2 ) and it adds a bit of drama which l like. Years ago now l purchased R.M. Williams boots in Australia and they are so beautiful and l always get compliments on them. And then one of the perks is watching Hugh Jackman do a video going around the factory, as he is their spokesperson. Joy 🙂

  8. I wear them with leggings or slim pants or jeans. Still very warm here in Texas . We really don’t cool off much till after Halloween. (sigh)

  9. Thanks, what is your suggestion for socks when you are doing skinny jeans, or when the ankle shows? I have heard no socks but would like you opinion

  10. 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!

    1. Ha! My name is Ellen and I could have written this same post, except I was not familiar with Jennifer in 2019. But spot on comments. I love booties, but am picky about how I wear them due to my short legs (5’5″ and curvy). Just bought a cute and very comfortable pair from the Buckle, but our Ohio weather has been hot & humid through mid-October so haven’t worn them yet. Great article Jennifer!

  11. 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.

  12. 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.

  13. 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.

      1. 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!

  14. 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.

  15. 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.

    1. 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.

  16. 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!

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

  18. 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.

  19. 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.