14 Secrets to Look Stunning in Over-the-Knee Boots

 be You want to keep your knees warm? This post is your ultimate guide on how to wear over-the-knee boots over 50 and look effortlessly stylish. This post explains how to style over-the-knee boots over 40, and how to wear over-the-knee boots to work in deep winter.

 

 

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 why we are expected to endure freezing temperatures on our daily commutes, during grocery shopping, or when picking up kids or grandkids?

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 a No-No for Themselves?

Not at least since the movie Pretty Woman, many people associate thigh-high boots with the red light district. They consider this footwear okay for a girls’ night out among 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 woman in cold weather in winter. These boots are beneficial to stay warm in windy and cold weather in winter. They are also advantageous when you have 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. When you live in a region with cold or severe winters, consider investing in the highest quality OTKBs you can afford, in a classic color that complements most of your cold-weather attire.
2. Opt for plain leather, as it’s best for keeping clean and neat, and is less susceptible to water/wet snow. In deserts or on dry days, suede works.
3. 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 the dress code requires them, choose a sturdy heel of up to 3 inches (7.5 cm) because they are not as hard to walk in on snowy or icy ground as thin heels. 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 in temperatures below freezing.
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; in the case of skinnies or riding pants, add a chunky or tight sweater/tailored shirt under a sporty blazer.
9. When pairing over-the-knee boots with mini skirts or short dresses, wear opaque tights, and go for a hand-width of space between the shoes and hemline.
10. When pairing OTK boots with cute dresses or skirts, choose a thick fabric A-line or pleated midi version with lining to prevent an awkward bulk.
11. Wear your OTK boots with a skirt or dress and opaque tights in neutral colors.
12. Only wear your over-the-knee boots outside. Switch to pumps or other work-appropriate shoes upon arrival to prevent sweating on your feet and/or knees. Sweat will freeze or evaporate, causing discomfort once you return outside.
13. Always opt for a look that clearly conveys a cold season aesthetic to appear sophisticated.
14. Skinnies and over-the-knee boots are a foolproof combination.

 

 

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

I wanted to go for a comfy, but polished weekend look. This look would also work for a Thanksgiving watching the games party. An Irish cable-knit sweater is nearly an American Classic since the Kennedy boys wore it early in the last century.

 

 

 

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 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 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 also important to accessorize your outfit in a sophisticated way.

 

 

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 exchange them. Here are my best tips for shopping on eBay.

 

 

 

 

 

 

 

 

Barefoot Over-The-Knee Boots

The barefoot shoes, aka minimalist shoes, mimic the experience of walking barefoot. Their typical design has a thin, flexible sole, a wide toe box, and a zero-drop heel, i.e., heels and toes are at the same height. These features provide feedback from the ground and foot mobility. Of course, you can also find them as barefoot over-the-knee boots. Style them in a casual way, similar to flat OTKBs.

 

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 in two pairs: one in silver for going out and one in brown for everyday wear. My other friend got them in red.

I bought a patent-leather black pair that I could dress up with a midi LBD for going out, or wear with comfortable cotton leggings for a casual look. Of course, these flat over-the-knee boots moved out of my closet a 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 genuine leather or suede with medium-high sturdy heels.

Then, all you have to do is to keep your outfit moderate casual or moderate classic, and use sophisticated accessories.

 

Photos: G. Kramm

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