Styling Ankle Boots This Fall
As the weather cools off and the ground gets messy, it’s time to swap out our summer shoes in favor of boots and booties. Not only are they one of the coziest footwear options for fall and winter, but I’m a big fan of their ankle support and the way they keep my feet dry in less-than-ideal weather. Today, Iām sharing some tips and styling ideas on how to wear ankle boots for women over 50, along with outfit inspiration and boot recommendations.
You might also enjoy reading Best Comfortable Womenās Shoes for Fall, Best Sneakers and Walking Shoes for Mature Feet, and Best Hiking Shoes and Boots for Women.
Knit booties have become a personal favorite because they stretch where my feet need it and accommodate my bunion without pinching.
KNIT STRETCH BOOTIES
Why Ankle Boots Are a Must-Have
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 womanās needs. There are also plenty of flat boots with flexible soles and arch support in varying widths, so thereās no need to sacrifice comfort for style.
How to Style and Wear Ankle Boots with Different Outfits
Ankle Boots with Bootcut, Flare, or Wide Leg Jeans
An ankle boot paired with a wider-leg jean like a flare or bootcut is such a natural combination. You’re able to skip the entire 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.
Ankle Boots with Straight Leg 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 shaft or they’ll snag the top of the bootie when you sit down and need constant adjustment as you go about your day. The closer fitting the shaft, the better they work with straight-leg jeans.
Ankle Boots with Skinny Jeans
These jeans aren’t super skinny, but they do have a narrow bottom. This type of jeans, along with a skinny jean, tends to look best with an ankle boot. Hem your blue jeans so that there is a small amount of leg showing between the jeans and the top of the boot. True skinny jeans look best with flats or tucked into knee boots.
Ankle Boots with Leggings
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
Ankle Boots with Dresses and Skirts
Pairing ankle boots with dresses and skirts can be incredibly flattering, but itās all about getting the proportions right. Knee boots are a classic look with knee-length skirts or dresses, but ankle boots can look just as flattering. Finish the look with tights that match your ankle boots for an elongated appearance. A pointed-toe bootie will also help make your legs look longer and is a nice option with a midi skirt.
Ankle Boots for Petites
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 a small heel, go for it.
The Best Ankle Boots for Women Over 50
You might have seen me wearing these low-heeled Munro booties in this post or this post. Their simple, minimalist design, almond-shaped toe, and neutral color make them an easy match for just about everything in my fall wardrobe. Their block heel adds a bit of height but is still super comfy and stable to walk in.
The shaft ofĀ this Easy Spirit Sidney bootieĀ fits nicely under my small bootcut jeans. They would also look nice with black tights and a skirt or casual dress. They’re incredibly comfortable with a comfy, low block heel, plus they’re orthotic friendly. Their arch support and cushioned insole make them wearable for long hours on your feet. They’re also available in brown or navy.
These Lifestride ankle booties are super comfy with a memory foam insole and a stable 1 3/8ā³ heel that feels virtually flat. They also have a gore inset that stretches when you walk. I bought the black microsuede, and they come in three other colors in sizes 5-11, medium and wide widths.
When the weather turns rainy or snowy, having a reliable boot to keep your feet dry is essential. While you could reach for a rugged, waterproof option, I prefer something that not only protects against the elements but also keeps me looking stylishālike this pair from Munro.
This platform bootie from Vionic checks all of my boxes for a solid ankle boot. Not only does the subtle wedge add a little height to your frame, but it has a removable, cushioned insole, arch support, an inset elastic panel, and zipper closure. It’s also made with water-repellent material. Available in three neutral shades in sizes 5-12 M and W.
Western or Cowboy boots have always been in style, and I’m seeing lots of western-inspired options this season. Tuck them under a bootcut jean or show them off with tights and a casual skirt. This pair from Naturalizer is available in both M and W widths in sizes 6-12.
Black and brown are classic choices, but why not switch things up with a pop of color like these red ankle boots or these blue ones? Pairing colored booties with a neutral outfit instantly adds a fun twist. Style Tip: If your booties are the only pop of color, the focus stops at your feet and stays there. To balance things out and draw attention back to your face, try adding a matching hue in a scarf, blouse, hat, or jacket. It creates a cohesive look that keeps the eyes moving upward.
Chelsea boots are a classic ankle boot that are never going to go out of style. They look great paired with a bootcut jean and a crewneck sweater for an effortless fall and winter look that’s both practical and polished. The double gore of this style will make them extra easy to step into and take off.
Shop More Ankle Boots for Women Over 50:
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.
- Booties with elastic side panels or zippers make it easy to slip them on and off with ease.
Are you a fan of booties? How do you like to wear yours?
This is unrelated to this blog post. I see lots of information on what to wear to a wedding. How about a post on what to wear to a Bridal Shower! In Houston, in February – it could be freezing or warm enough to go swimming! It will be a ladies shower, in the afternoon in someone’s home. We have been asked to wear blue. Can’t wait to see what if anything you come up with! Thank you in advance. Happy 2025!
Do you have an opinion on BZee brand booties? I bought a pair a few weeks ago and after one wearing, I had a serious blood blister on my toe. In their defense, that foot is fairly banged up, due to an addiction to pickleball. I specifically bought the Wide width, though and the upper material was fitting very well, I thought.
I have no experience with that shoe.
I really like to wear booties. I own 4 different styles. Thanks for the post and the great variety.
I have four pairs of booties but the weather until today has been too warm to wear them. We had a hard frost last night. Today is a slip in Skechers shoe as I am feeling my flu shot. Just a little nausea and fatigue. I will take it easy after I fold up two loads of towels I washed this morning. Enjoy your cool rainy day.
I hope you feel better soon
Great selection of booties. My favorite footwear for fall & winter. Love Munro, I have a pair from years ago that still look terrific. Iāve never tried stretch booties, might give them a try.. Happy Halloween, it was nice to Eakins up yo some rain this morning
Happy Halloween!!
Jennifer, what are your thoughts on wearing ankle boots with wide leg crop jeans/pants, for us older ladies. Like the crop gaucho jeans you have from Frank & Eileen. Would you wear those with an ankle boot. I have a few of that crop style of jeans from the summer and I wonder if I can make them work this Fall with boots.
I will wear mine with the sock booties, for sure. A wider shaft could get stuck on the top of a wider bootie. I’m also thinking they would be great over a knit knee boot. I left F&E gaucho jeans in Vancouver ( why oh why did I do that?) so I’ll have to try when I get back up there.
I love all these booties. I have never seen stretch boots but they look really comfortable.
Theyāre great! Really comfy.
Thank you for the wonderfully researched choices of booties along with your comments and recommendations. Definitely something here for everyone. There are quite a few ads on your site for the knit Vivaia booties and shoes. I wonder if you have tried them and can comment on them as well?
I havenāt but Iām a huge fan of stretch booties so maybe I should try them š
Hi Jennifer, I really loved the brown suede booties you had on yesterday, where are they from and do the ship to Canada?
They are selling out fast. I found some Here from Amazon. Hopefully theyāll ship to Canada.