How to Style Ankle Boots: Modern and Timeless Looks for Any Age
Fashion trends come and go, but certain staples—like ankle boots—are timeless. What does change, however, is how to wear them. A classic ankle boot can instantly elevate your outfit, but the secret to making them feel current is all in the styling.
Today, I’m helping you tweak your chic at 40, 50 and beyond by sharing everything you need to know about wearing ankle boots in a way that’s modern, flattering, and age-appropriate.
Styling Ankle Boots – Things to Consider
Looking fabulous in ankle boots is about more than just finding a cute bootie. You need to think about heel height, material, where you will be wearing the booties, and what you plan to pair with them. Let’s get into these details and look at a few outfit combos at the end for inspiration.
But first…
What are Ankle Boots?
Ankle boots end at the ankle or a few inches or above. They were introduced in 1804 as fashionable women’s wear for outdoor activities and riding and have been around ever since. The reason? They strike the perfect balance between comfort and chic.
Are Ankle Boots Still in Style?
Ankle boots are still 100% in style in 2025, so long as you style them in a modern way. These days, you’ll find hundreds of styles of ankle boots from Chelsea to Mod, Combat, and Sock booties, and the options for what to wear them with are endless.
Ankle boots continue to evolve with fashion trends. At the same time, the core silhouette stays the same, with details like toe shape, heel height, and material shift to reflect what’s current. So, if you want your look to feel fresh, you’ll want to pay attention to those little details.
Tips to Keep in Mind When Styling Ankle Boots
Which is more in style, tall or short ankle boots?
Did you know there’s a difference between “ankle boots” and “ankle booties”? It all comes down to shaft height. Tall ankle boots extend one to four inches above the ankle. This style is actually more on-trend right now because it adds a more structured and sophisticated touch to your wardrobe.
Ankle booties, on the other hand, hit just at or above the ankle. They’re the more classic option, suitable for casual looks. Even though ankle booties aren’t as trendy, they’re a timeless staple you can always count on. Short ankle boots look particularly good with slouchy jeans where the hem covers the ankle of the boot, anyway!
Should your ankle boots be tight or loose?
When people say “loose” ankle boots, they’re probably referring to the trendy older sister of classic ankle boots—slouchy boots! I’ve talked about them a few times on my blog before; they’re cozy and chic and easy to dress up or down.
Slouchy boots are actually the trendy choice—are you surprised? They give you that “boho babe” look, but it’s not for everyone. In that case, tighter ankle boots give you a more slimming effect and look much better than slouchy boots with certain pant styles.
Can you wear colorful ankle boots?
The right pair of shoes can make or break your outfit, so have fun with them! I’ve posted my fair share of sleek black ankle booties and elegant winter whites. But have you seen my posts on how to wear red ankle booties or edgy snakeskin prints?
Color or printed ankle boots can give your outfit a new life, but make sure you pair them with neutrals so everything looks good and balanced! Also, consider what season you’re wearing them in. These smoky taupe booties, for example, would look stunning in the summer, whereas these “Cafe Noir” boots would WOW in winter. See how the difference in shade makes all the difference?
Which is better, pointy-toe or round-toe ankle boots?
The pointy-toe will always be a fab choice, and I don’t just mean for ankle boots! Any pointy-toe shoe will make your legs look like they go on for miles. If pointed-toe shoes are too powerful for an outfit, almond or square-toed may be more your speed.
Round-toe boots are usually more comfortable, but some can look dated, especially the low-heel ones.
What heel shape will complement your style the most?
Chunky, stiletto, kitten, flared—with heel shape is the most stylish??? Like with everything else, it depends on what you wear.
I think I speak for us all when I say that even though stilettos bring some drama, they’re just not practical (or comfortable, lol!). Block and kitten heels are the perfect compromise. You get the height and comfort, and they tend to go with just about everything. Plus, you can bet they will make an outfit look elegant and feminine!
Suede or leather—which looks best?
Suede ankle boots add a bit of whimsical touch to a look. Think boho dresses, flowy skirts, or even the right pair of jeans. This style tends to pair better with more casual outfits. I really love wearing suede when it starts to get cool outside since they’re warm and cozy!
When you want a pair of ankle boots that look sleek and polished, go with leather! They’re timeless, versatile, and just as comfortable. You can pair them with anything from a moto jacket for a sexy and mature look or a pretty floral wrap dress to add a bit of sophistication. And they don’t always have to be sleek black leather. Look at these brown crocodile-printed ankle boots!
Timeless Ankle Boot Looks With a Modern Twist
Now that I’ve gone over all of the important tips for wearing ankle boots let me give you a few examples. If you need some inspiration, let these looks be your starting point!
Monochrome Look With Snakeskin Boots
Black skinny jeans with a black cardigan and a white tank create a striking monochrome look. Add snakeskin ankle booties for some print and texture, and the outfit looks chic and timeless.
Warm and Cozy in Suede (don’t love this heading)
For a warm winter look, try suede ankle boots with a funnel neck sweater. It still has the elegance of a turtleneck, but it isn’t as bulky. To keep the look timeless, wear dark wash jeans and add a few classic, dainty pieces of jewelry.
Wild in Western Ankle Boots
Western ankle boots are fun and trendy! But instead of looking like you’re on your way to the rodeo, this pair looks modern and sleek. Plus, the pink-shirred blouse with jeans puts a nice feminine touch to the overall ensemble. So cute!
Ankle boots are still in style; you just need to know how to style them!
Ankle boots will always be around, but looking great in them all comes down to how you style them. Pay attention to what you wear with your ankle boots. Match complementary colors and fabrics, and wear them in ways that make sense for the occasion. Tweak your chic.
Be sure to check out my LTK storefront to see all of my favorite outfit ideas. And keep up with my blog for each new post. You can also join my private Facebook group, Fabulous After 40 Dressing Room, to discuss your thoughts on ankle boots. Do you love them or hate them? I’d love to read all about it in the comments below!
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