skip to Main Content
Over The Knee Boots | CrunchyTales

Style Temptation: How To Sport Over The Knee Boots In Your 50s

4 min read

There’s something provocative, but also stylish, about over-the-knee boots. That’s probably why, even though sometimes challenging to sport, since the early 1960s when Balenciaga’s fall collection featured a tall boot by Mancini that just covered the knee, the popularity of what french stylists call Cuissards has never waned.

But still, many women over 50 prefer not to invest in these statement shoes as they are wrongly considered not appropriate for their age. What we often forget is that most of the time when it comes to updating our look all we need is to choose a style that flatters our body-type.

Whether you opt for the ones in leather or suede, flat-soled or with block heels, high heels or stiletto version, in the end, is all about finding the right proportions. And although they might seem daunting to wear at first, they’re practically like any other pair of boots you already own. They simply hit higher on your leg, which is really convenient when it’s chilly outside.

These boots are also pretty versatile. They can be worn for dressed-up occasions with dresses and gowns or every day with trousers and skirts to add a nice fun element.

The general rule of thumb is to find the perfect pair of boots that sit comfortably above the knee without either cutting into the back of your knees or falling down. If they sit at an awkward height it can feel uncomfortable or look less flattering.

If you’re just warming up to the idea of wearing over-the-knee boots in your 50s, here are a few tips to follow and then avoid the Pretty Woman look.

Keep it simple and classy

In general, steer away from wearing them with bare legs and instead pay attention to the length of your pants or skirts in relation to the top of your boots (too much of a gap can make you look shorter and a bit tacky).

Also, avoid plastic-looking fabrics and instead focus your efforts on keeping the colour palette cohesive with your overall look to elongate your silhouette. And when it comes to fit, choose those ones that are a bit tighter around the legs as they have more structure so they stay up and fall down less.

For the heel, you ideally want to buy shoes that suit a more casual way of dressing and are comfortable at the same time, so lower ones are perfect.

The best way to rock your over-the-knee boots at any age is to go for a flat to 2-inch heel height to ensure you look chicer or opt for a flat relaxed fit and chunky sole for a more casual style that’ll give you both comfort and increased height, and because of their versatility, you can basically wear them anywhere, from a business meeting in the morning to an event at night.” says stylist Rebecca Thompson.

SEE ALSO:  8 Charity Gifts Ideas For Christmas 2021 

But what if you are petite?

Unless you’re a model, over-the-knee boots can be somewhat challenging to pull off. The fact that they cover well over half the leg means that they can dominate your lower half. This draws eyes downwards and creates weight on your lower legs, making you appear shorter than you are.

For petite women, Thompson recommends trying a boot with a heel either wedge-style to a low-heel stiletto that best suits your daily routine and wardrobe.

Avoid slouchy styles and stick to boots that are more narrow and streamlined. Try pairing them with a sweater dress for a fabulous day-to-night look -just remember to have an inch or two of skin showing to avoid looking overpowered by fabric“, she continued. “Also remember to never fold down the boot, which can quickly become a piratesque look“.

Winning Combinations

A classy combination is pairing the boots with skinny trousers or leggings, a long sweater or blouse and your favourite cropped coat.

Skinny jeans tucked into over-the-knee boots styled with a tie-front top and a leather jacket is a classic autumn outfit – says fashion designer  Tan France -. For a winter outfit idea, pair black suede OTK boots with opaque tights or leggings and a turtleneck tucked into a mini skirt. Add a fuzzy or wool beret for retro-chic flair“.

But you can also sport them underneath a flowing maxi dress or midi skirt for a boho look. Even better is if there is a side slit that allows you to show off your footwear with every step you take.

If you like the bohemian look, wear over-the-knee heeled boots with a full skirt 2-3 inches below the knee and pair them with a peasant blouse“, suggests Sue Heuman, a member of Nordstrom‘s Canadian Advisory Panel and a Poppy Barley Ambassador. “Accessorize with a chunky necklace made with natural materials such as wood and leather to complete the look“”.

Even a pencil skirt with a structured blazer and dark tights would work with over-the-knee boots if you are looking to achieve a sophisticated look.

Whatever combo you go with, one thing’s for sure: knee-high boots have big main character energy. So, what are you waiting for? Choose your over-the-knee boots in grey, brown and cognac (the new “it” colours) and in soft suede varieties to start enjoying endless possibilities of standing out from the crowd. Your confidence boost might just be a pair of brand-new Cuissards.

Like this post? Support Us or Sign up to our newsletter to get more articles like this delivered straight to your inbox!

Back To Top

Learn how to make the most of your midlife journey. Get your Free Pocket Guide on “How to Age Playfully”


Learn how to make the most of your midlife journey. Get your Free Pocket Guide on

Free Pocket Guide | CrunchyTales

"How to Age Playfully"