40+ Style: How to Wear Ankle Boots Over 40 

how to wear ankle boots over 40

Choosing the right pair of shoes is a daunting task, especially when you are a woman over 40 and comfort is your priority. So, here we present you with a brief guide on how to wear ankle boots over 40 in smart ways with convenience and style.

Getting your hands on a good-quality pair of boots is an expensive investment. So, why not choose the one that gets you through all seasons in style. Ankles boots are among those rare boots types that you can slay at work and on weekends all year round with your fashion game in check.

Ankle boots are more of a wardrobe essential because of their ability to go along well with most outfits. So, stick with us to know fashionable ways to style your ankle boots effortlessly. 

Do’s And Don’t Of Styling Ankle Boots For 40+ Women

  • Always wear your pants above your ankle shoes. The hems of the jeans tucked into your boots or folded above are a chic way to do so.
  • Try to match the color of your pants or jeans with your boots for a tall look.
  • Do not wear contrasting color socks with your boost; a pair of matching socks will look good.
  • Wear low-cut ankle boots with your summer outfit for a trendy look.

How To Wear Ankle Boots With Jeans?

Although, you can style ankle boots at any time of the year. But, it is ideal footwear to wear when the temperatures are moderate; too cold for sandals, and too hot for tall boots. The most effortless way to wear your ankle boots is with jeans. Wearing ankle boots with jeans is a classic outfit, in the trend for years now. So, here are a few trendy jeans fashions to wear with boots.

Skinny Jeans

Skinny jeans are the one type that can be styled with any form of ankle boots. You can never go wrong when styling with skinny jeans, whether it’s a  pointy toe, chunky heels, pencil heels, mid-calf, or low-cut ankle boots. Each one of them will depict a unique style when worn correctly.

Boot-cut Jeans 

Unlike other jeans, the flared hem will lie over the boots when styling boot-cut jeans. While choosing the ankle boots with your combat jeans, always opt for a heel. A pair of chunky heel dress boots with jeans is a perfect outfit for a sunny spring evening.

Straight Leg Jeans 

Straight-leg jeans are an ideal pair for a laid-back look. Although you can wear these jeans with any ankle boots, combat boots with jeans are the most suitable outfit combination for styling a black boots and jeans outfit.

Cropped jeans 

If you do not want to style your jeans with a folded hem ankle boot outfit, try wearing them with cropped jeans. A decent top and cropped pair of jeans with Chelsea boots are the perfect outfit combination to adorn on any casual evening. In addition, wearing a leather jacket with this outfit would be a cherry on top.

Mom Jeans 

If you want to style a voguish winter look, a pair of mom jeans with booties is your outfit. Style a body-hugging woven sweatshirt and wear your favorite baggy mom jeans and ankle boots with heels for a street-smart winter outfit. Moreover, carrying a cross-body bag with a black leather belt will elevate this look beyond measures.  

Boyfriend Jeans

If you are looking for some ankle boot outfit to wear in summer, a pair of boyfriends is all you need for a cool vibe. For this purpose, wear your faded boyfriend jeans with a white t-shirt and style this outfit with a matching pair of ankle boots. In addition, wear a stylish pair of sunglasses to add instant glam to this entire look.

Outfits To Wear With Ankle Boots Over 40

Although it is a fact that no other trend is more prevalent in 40+ fashion than a jeans outfit, as a woman over 40, you cannot always wear jeans with your ankle boots for every occasion. There is also some other outfit combination you can slay, putting your ankle boots on. So let’s discuss a few such outfits in detail.

Leggings Outfit

You can wear a legging outfit with low-heeled or flat ankle boots without thinking twice about the weather. For instance, a pair of black leggings styled with a simple oversized shirt ankle boots is a trendy casual look you can carry on an ordinary day. In contrast, a sweater dress with a pantyhose and ankle boots would be a tremendous semi-formal winter look. You can always layer this look with a peacoat for added warmth and style.

Boots With Dresses 

One of the most vogue ways to style your ankle boots is with a dress. Whether it’s a flared midi dress, floral maxi, or a wrap dress, a pair of stylish high-heel ankle boots will complement each one equally. Moreover, you can always add some blazer or trench coat to transform this look into a chic winter wear outfit. Lastly, adding some nice accessories like a neck scarf or a pair of sunglasses won’t hurt anyone.

Jumpsuit Styling With Boots

A raging trend nowadays, Jumpsuits create a unique style statement when styled with a pair of ankle boots. So, if you want to be the ultimate head-turner with your styling game, try wearing a wide-leg jumpsuit with a matching pair of chunky heels booties. Throwing a contrasting jacket or a blazer over this outfit would be a cherry on top. Moreover, pulling off the same look with a romper outfit will also make it work for summer days. 

The Skirt Outfit 

Style your mini skirt outfit with matching ankle boots for a bright summer look. Wearing a few accessories, a handbag, and sunglasses will elevate this entire look beyond measures. On the other hand, you can also style a maxi skirt with a pair of ankle boots to create a fun holiday look. Wear a leather blazer or a jacket with the above-defined look in cold weather.


Wearing Trousers or pant outfits with low-cut ankle boots is a clever way to upgrade your workwear game. In addition, an office blazer with a sleek bun hairstyle and a tote ba would make this look even more professional. Moreover, you can also style this look for a casual vibe by pairing it with a printed blouse outfit.

Above Ankle Boots With Shorts 

Denim shorts outfits look flattering and add a trendy casual vibe to your entire look. Wearing a pair of ankle boots with a t-shirt and denim shorts is a classic way to upgrade your casual look. Adding a stylish shacket or blazer and sunglasses will make this look pop out more. With your fashion game on point, you can wear this look to a college tailgate, a football match, or a casual trip to the grocery store.


How to wear jeans with ankle boots in 2023?

Wearing jeans with your ankle boots is the easiest way to pull off a chic look. Jeans with a flared hem can be worn the regular way, while for skinny or straight leg jeans, tuck the hem into your boots or fold it above your ankle for maximum style. You can pair this combination with any summer or winter to create a style statement.

How to wear Chelsea boots with jeans?

You can wear your Chelsea boots with cropped skinny jeans, a straight leg, or mom jeans. The type of jeans with wide legs or flared hem does not go well will flat boots. So, pairing them with boot-cut or boyfriend jeans will not work for you.

How to wear skinny jeans with boots?

Skinny jeans are the most appropriate and effortlessly modish outfit to wear with boots. Style your regular skinny jeans with a pair of boots by tucking the extra fabric into your knee-high boots. Alternatively, you can go for cropped skinny jeans to create a fabulous outfit to wear with your ankle boots. 


Ankle boots are the most sought-after trend in 40+ fashion. These versatile boots can be worn with almost any outfit, at any time of the year, regardless of the season. You can wear it with a t-shirt and jeans outfit by tucking all hems into your boots. Alternatively, you can also style them with jumpsuits and dresses for a breezy summer look. On the other hand, a trench coat or leather jacket paired with leggings or a skirt would be a sober outfit to carry on a chilly winter evening.

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