How To Wear Ankle Boots Over 40

A few days ago I was waiting for my friends at a cafe. At one point, unintentionally, I overheard a bevy of middle-aged beauties sitting next to my table, and they were discussing ankle boots fashion. Mostly they weren't sure if they were supposed to wear pants or skirts with over-ankle boots to look classy and charming.

The higher knee boots, over-ankle boots, or even short boots with skirts has become pretty mainstream. You can style them with anything; you want to wear, be it your favorite jeans top combo or frock with a long sweater. Fashion is all about confidence. Right?

How To Wear Ankle Boots Over 40

However, if you are over 40, 50, or more and want to ensure you’ll not look trashy with your experiments on platform boot outfits, hopefully, you’ll get all your confidence back by the end of this style guide. Today, I’ll focus on some trendy ideas for how to style boots or women’s ankle boots over 40.

How To Wear Ankle Boots Over 40

How to Wear Ankle Boots with Dresses?

Sometimes, you may look weird depending on the season, events, or place, if you choose the wrong outfit. Suppose you’re planning to wear revealing clothes in a chill winter to look alluring, but unknowingly you’ll look weird at the end of the day.

So, you’ll need to choose the right attire to wear by following these seasonal style rules –

During Spring

Comfort is king, but spring is the time to say goodbye to the coziness of cardigans, and furry blankets. This time you could try bright dopamine dressing to boost your mood and welcome the first blossom of spring.

When you’ll wear brightly colored floral dresses, wrap, or tea dresses, it would be a nice decision to go with brown or light-colored ankle boots.

Spring Dressing For Ankle Boot

During Summer

Summer is a good time to bring out your all-sleeveless dresses, minis, midis, and other short dresses to look alluring, as well as a little extra air circulation.

You can pair tan or brown ankle boots with mini floral dresses, midi linen, or patterned printed dresses to get a cool and stylish look.

Summer Dressing For Ankle Boot

During Autumn

Autumn is the time to embrace cozy winter, so if you want a cute and cozy look during these months, try coupling the skater dresses with black or brown ankle boots.

Autumn Drees For Ankle Boot

During Winter

Winter is the perfect time to make use of your favorite cozy cardigans, sweater, or warmest full covered dresses. Pair them up with shiny black ankle boots for warm style.

Winter Dress For Ankle Boot

Style Guide on the Different Kinds and Colored Ankle Boots and Dresses

I’ve noticed people often wander around their closets thinking about what to wear with black booties. How to style a night out red ankle boots outfit? Ankle boots will look great with all kinds of dresses if you pair together the right styles.

Different Type Of Ankle Boots
  • Suppose you want a gorgeous black bootie outfit. You will look stunning if you wear a floral dress or solid-colored, well-fitted velvet dress with tights and black boots in the cooler months.
  • You can pair any brown ankle boots, be it suede brown, chunky brown, or lace-up brown ankle boots, with all kinds of summer dresses.
  • If you want an edge of trendy sophistication in your tight leggings and ankle boots outfits, you can try the darker-heeled ankle boots. They will even create the illusion of having sexy long legs.
  • The most comfortable flat ankle boots go well with casual dresses, like comfy sweater dresses, t-shirt dresses, or skater dresses. Such outfits are perfect for day-to-day wear; they suit everyone. 

What to Wear With Chelsea Boots Women's?

Chelsea boots have been around since the 1950s, are still popular in 2022, and never seem to go out of fashion. People love these over-ankle shoes because of their style compatibility with endless outfit possibilities and the comfiest nature. They are available in varying widths with plenty of arch support and flat or low-heeled flexible sole options.

Chelsea Boots Outfit For Women

Such ankle-high boots are super stable around your ankle, and highly supportive at the arch; plus, it keeps your feet warmer and dry during nasty scorching summer or chilled weather.

However, there is no particular rule like Chelsa boots should be worn with jeans or skirts. You’ll look as amazing with jeans as you look with a floaty floral skirt.

Apart from jeans and skirts, the women's Chelsea boots will also look great with midis, mini skirts, leggings, joggers, patterned pants, leather pants, and jacket pairs. 

How to Wear Chelsea Boots Women?

Along with things of choosing the proper outfit depending on the weather, you can nail the iconic look you want with your chosen outfit by following these wearing styles -

  • Wear Chelsea Boots with Skirts over 40, or more

In middle age, you could go out with a super edgy look by wearing a gray sweater, black midi skirt, black ankle-length Chelsea boots at your feet, and a black Panama hat on your head.

Tights or leggings are a cute way to wear a mini skirt if you want to be less revealing. Pair together a chunky sweater, gray or light-colored mini skirt, black tights, and black boots to rock in Chelsea boots.

  • Wear Chelsea Boots with Pants

You will be super cute and attractive too in an untucked button-up solid-colored shirt, leather jacket on it, color-matching checkered pants, and Chelsea boots.

You can try different colored, washed, and styled jeans. If you want to show off your gorgeous Chelsea boots, wear cuffed jeans or any jeans just slightly over the top of the boots, and even you can roll up the bottom of the jeans a bit.

You can wear straight-leg or skinny jeans with desired top either tucked into the boot or just over the top. Some people wear Chelsea boots and tuck them into a pair of long socks to make the boot noticeable.


No matter, what outfit you’re carrying, just wear it with the fullest confidence to pull off any look. So, stop giving and even thinking of any age-related excuses we often come to hear from others.

Now, it’s the time to step forward towards exploring endless outfit possibilities with your higher-ankle boots. I believe that the surrounding people will adore your fashion sense for sure. 

Leave a Comment

Related Posts