13 Secrets to Look Stunning in Over-the-Knee Boots (2024)

You want to keep your knees warm? This post is your ultimate guide how to wear over-the-knee boots over 50 and look effortlessly stylish.

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Do OTK Boots Have an Age Limit?

The statement comes up again and again that women over 25 should not wear over-the-knee boots! Can someone explain to me why we are supposed to freeze our knees off in below freezing air on the commute to work, when shopping for groceries or picking up the kids or grand-kids somewhere?

The statement should be that women of any age should not style them like Vivian Ward in Pretty Women.

Why Do Many Women Consider OTK Boots as a No No for Themselves?

Not at least since the movie Pretty Women many people associate thigh-high boots with red light district. They consider this footwear ok for a girls’-night-out of our twenty something sisters, if at all. Otherwise it is a uniform for those professions. Patent leather stiletto OTK-boots are otherwise costume.

Over-the-knee Boots Work at Any Age

… for every women in cold weather in winter. These boots are very helpful to stay warm in windy and cold weather in winter. They are also advantageous when you had no opportunity to plug in your car or park it in a heated garage. Over-the-knee boots provide long enough insulation in the car until the car heating kicks in. See, there are many mature reasons for a woman in midlife to wear OTK boots. Now how to get it right?

What Are the Secrets of Wearing Over-the-Knee Boots Right?

1. Invest in your over-the-knee boots when you live in a region with cold or severe winters. Buy the highest quality you can afford in a classic color that matches well with most of your cold weather attire.
2. Go for suede or plain leather, not patent leather nor pleather. Plain leather is best to keep clean and neat, and least vulnerable to water/wet snow.
3. You will never look stylish when your face screams uncomfortable. Choose a wide toe box for comfort or go half a size up so you can wear a pair of extra socks inside. Squeezed toes mean cold toes.
4. When you like heels or your office dress-code requires heels, choose a sturdy heel of up to 3 inch (7.5 cm). Thin high heels are hard to walk in on snowy, or icy ground. Look for a thick sole, not a plateau.
5. The design should match your primary personal style.
6. Only wear your over-the-knee boots at below freezing temperatures.
7. Avoid anything too glam, lacy or sexy.
8. Over-the-knee boots look best with wide midi skirts that cover them totally, skinny jeans or riding pants. In the case of wide skirts, add a slim/tight sweater or twinset; incase of skinnies or riding pants, add a chunky or a tight sweater/tailored shirt under a sporty blazer.
9. When pairing over-the-knee boots with mini skirts or short dresses wear opaque tights. Go for hand-width of room between the boots and hemline.
10. When wearing OTK boots with cute dresses or skirts the safest way is a thick fabric A-line or pleated midi version with lining to avoid weird bulk.
11. When you pair them with a skirt or dress that does not cover them fully, wear opaque tights in neutral colors. Yes, bare legs with OTK boots are a no no for everyone except for women in the horizontal or vertical professions.
12. Only wear your over-the-knee boots outside. Switch to pumps or other work-appropriate shoes when you arrive at work to avoid that your feet and/or knees sweat. Sweat will freeze/evaporate and cause discomfort, once you are back outside.
13. Always go for a look that clearly says cold season to look sophisticated.

Step-by-Step How to Style Casual Weekend Looks with OTK Boots

I wanted to go for a comfy, but polished weekend look. Note this look would work for a Thanksgiving watching the games party too. An Irish cable-knit sweater is nearly an American Classic since the Kennedy boys wore it early last century (more on the history of cable knit sweaters).

The following look goes for an American West vibe with a suede jacket, sweater and silk scarf. In very casual or creative work environments in the American West, this look may even work as an outfit for Casual Friday.

The look below varies the above styling recipe. In the look above, the accessories twist the look to a blue-brown-gold color-scheme, while in the one below, they create a blue-brown-pink color combination.

The photos below show how modest the above outfit gets when paired with a long coat. Then your thigh-high footwear looks like a winter look with a skirt or dress. This outfit clearly shows that the footwear is for insulation to stay comfortable and in style in cold wet weather outfits.

Can You Wear Over-the-Knee Boots to Work (Explained Example)?

The next photo shows over-the-knee boots with my floral tweet skirt, denim jacket, cashmere sweater and a chambray shirt. The skirt is the link between the OTK boots and the denim blue. It’s important to also accessorize your outfit in a sophisticated way.

See another example of a sophisticated work outfit with OTK-boots with pink and brown.

Photo Inspirations How to Style Otk Boots

When styling your OTK-boots, your goal is to create a mature, powerful and serious look.

Tip: You often can find brand-new items on eBay that were gifts, but they did not fit (physically, taste, etc.), or the buyer had lost the receipt to be able to exchange it. Of course, you can’t go on eBay with the idea to find something right away. You have to browse long and frequently. Here are my best tips for 5 star shopping on eBay, in case you missed them.

See Also

Sweaty Feet: How to Manage Sweaty and Smelly Feet

Over-the-Knee Boots in the 1990s

My girlfriends and I bought our first pairs right after we saw Julia Roberts wearing over-the-knee boots in Pretty Woman. We all chose a flat pair to avoid association with Vivian’s job. My friend Katherine invested even in two pairs, one in silver for going out, and one in brown for everyday. My other friend got them in red. I bought a patent-leather black pair which I could dress it up with a midi LBD for going out otherwise wear leggings. Of course, these flat over-the-knee boots moved out of my closet long time ago during one of my closet overhauls. The reason: They were worn out.

Tip: When you had your first pair in the 1990s like me, don’t style them with leggings. It’s yesteryear.

Conclusions on How to Wear Over-the-Knee Boots at Any Age

The secret is styling OTK boots over 40 starts with the boot-style. Search for a great, high quality pair of over-the-knee boots that are serious. Look for classic details like a not too round, not too spiky toe box, and European classic boot colors (brown, tan, gray). Go for real leather or suede with medium-high sturdy heels. This means clearly veer out of Pretty Woman’s territory to look Young and Hip without looking like trying too hard.

Then, all you have to do is to keep your outfit moderate casual or moderate classic, and use sophisticated accessories like shown in the example outfits.

Photos: G. Kramm

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