You are currently viewing 13 Secrets to Look Stunning in Over-the-Knee Boots

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).


older woman wearing over-the-knee boots with skinnies as weekend look
Dior over-the-knee boots with J Brand skinny jeans, Festina watch, Hermes collier de chien bangle, Orvis Irish cable-knit sweater and leopard pendant necklace for a casual, but polished weekend look. I found this pair brand-new on eBay a couple of years ago in summer.



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.


over 50 years old woman wearing a casual winter outfit with over-the-knee boots
Orvis suede blazer, GNW Luxe cashmere wool sweater, J Brand skinnies, Dior over-the-knee boots, silk scarf and necklace.


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.


Classic winter outerwear look with OTK-boots
Orvis suede blazer, GNW Luxe cashmere wool sweater, J Brand skinnies, Dior over-the-knee boots, silk scarf, necklace, Festina watch, striped winter coat (thrift store find), head band, LeatherCoatsEtc gloves and Longchamp satchel.



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.


over 50 years old fashion blogger with knee-length tweed skirt, denim jacket sweater, shirt and OTK boots over-the-knee boots
Great Northwest denim jacket, Oliveo button-down shirt, cat pendant necklace, Brooks Brothers cashmere sweater, Hermes collier de chien bangle, Ann Taylor floral tweed skirt, Arm party: Golden bangle gift from my late mother, enamel bangle gift from my girl friend, Hermes enamel lion bangle, and Tissot stone watch.


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.


collage of fashion blogger over 50 in Casual Friday work outfits with thigh high boots
Left two photos: Burberry plaid blazer, Gucci scarf, J Brand jeans, and croc-impress belt. Middle right: Eli Tahari leather sheath with GNW cashmere sweater, LV silk scarf, and 3.1 Philip Lim bag. Right: Ann Taylor floral tweed skirt, Oliveo button down shirt, statement necklace, Hermes collier de chien bangle, Tissot watch, Longchamp bag and Oliveo cropped blazer.



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.



collage showing how to style otk-boots for the office with skirts, sweaters and cardigans
Business Casual over-the-knee boots outfit ideas. Left: Bias-cut plaid skirt, Landsend mock neck sweater, smoky quartz necklace and bracelet, Gucci belt, GNW tight. Middle: Gucci silk scarf, Pendleton glen check pleated midi skirt, Hermes collier de chien bangle. Right: GNW leopard print cardigan worn as top, Moda International dyed cardigan worn, Jord bamboo watch, Pendleton glen-check pleated midi skirt and Hermes collier de chien bangle.




Alaskan fashion blogger in tall boots, shearling coat, headband and orange skirt
Styling tip: Roll your boots down. Unbranded headband, GNW Luxe cashmere wool sweater, gemstone necklace, Gucci scarf, Vittori shearling coat, Max Mara skirt, GNW tight, citrine earrings, LeatherCoatsEtc gloves, and Bellorita bag.



collage of style book author in otk suede caloches with skirts and jackets
Left: Plaid skirt, Gucci G belt, Andrew Mark shearling motorcycle jacket, LeatherCoatsEtc gloves and beret, 3.1 Philip Lim tote, smoky-quartz necklace, and cable-knit sweater. Middle: Diamond-leopard print jacket, Pendleton skirt, Longchamp satchel, silk neckerchief and LeatherCoatsEtc gloves. Left: GNW Luxe sweater, unbranded denim jacket, Festina watch, Carhartt gingham shirt, three string pearl necklace, Ray Ban aviators, YSL bag, Hermes collier de chien bangle.




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

© 2013-2023 Nicole Mölders | All rights reserved

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This Post Has 5 Comments

  1. Sorry to hear you broke your foot. I hope everything healed well so you don’t have any long-term issues.

  2. I am so glad you linked this post up with us for the Ageless Style link up. I have a pair of OTK boots that I bought several winters ago then promptly broke my foot and couldn’t wear. I have trouble thinking outside the box so could only envision wearing them with skinny jeans. I love the looks you shared showcasing the boots with skirts. A+!! I can do this. You look smashing in every picture and provided so much great inspiration. Thank you!!

  3. Yes, anything that reads 1970s or 1980s would look yesteryear on women over 50. A Millenia, however, could wear such a pair as a fashion statement within the retro trend when styled with modern (not vintage/not retro pieces).

  4. Kathleen

    I think you need a new, updated model with classic choices.

  5. You look amazing in your over-the-knee boots.