over-the-knee bootsI often get asked whether Over-The-Knee boots are appropriate for women over 40. My personal feeling is that it really has more to do with the overall styling than does with age. And trust me, there are ways to pair over-the-knee boots without venturing into the hooker look territory – unless, you want to.

My best advice to wear over-the-knee boots that is best for every age is to pair them with skinny jeans in pure indigo, dark wash or black colors. Over-the-knee boots have made the way as one of the cold-weather wardrobe staples and won’t go anywhere anytime soon.  If you do not have a pair in your closet I highly recommend to invest in a good pair.

Here are five effortless ways to wear them to keep you looking and feeling your best whether you’re 20 or 70!


One of the easiest ways to pair your over-the-knee boots with closet staples you probably already own, that is, your favorite sweater and skinny jeans. This style is universally flattering and the boots can instantly elongate and slim the legs.


Another look that I often wear with over-the-knee boots is a long sweater and thick leggings.


Every girl should have a sweater dress in her fall/winter wardrobe. They are cozy and warm. Nothing says laid-back glamour like a cozy and warm sweater dress paired with over-the-knee boots.


I can’t stress enough how well over-the-knee boots work with maxi skirts/dresses, especially in the cold weather. This is my favorite go-to style if I want to stay warm while looking stylish in a maxi dress/skirt.


Over-the-knee boots look really stylish with a mini skirt too. My advice is to remember to have an inch or two of skin showing to avoid looking overpowered by fabric, especially if you are petite like me.

I found a few styles of affordable over-the-knee boots to inspire you to rock this style with confidence.


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  1. I love the over the knee boots. They are so perfect with just about anything you could wear!

  2. I style them over jeans. Sometimes I will roll them down too. Hard to really play up too much with all the snow we have been getting.

  3. I have actually always wanted to try over the knee boots, but I’m afraid I would look like a new born baby deer with how skinny my legs are and how i can’t really walk in heels 😂. These are all cute styles!

  4. These look so great on you. I admire they way you carry fashionable clothes with elan! You are an inspiration to many girls out there! Keep up the good work!

  5. Thanks for all these useful tips! I’m petite and I haven’t tried wearing over the knee boots. They all look so fashionable!

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