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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 and Independence Day many women (and men) 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. Thus, 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?

Today I share the secrets of how over-the-knee boots can be styled in an ageless way that works for every woman, even Vivian Ward.

  1. Invest in your over-the-knee boots when you live in a region with cold winter climate. Buy them in the highest quality you can afford in a classic color that matches well with most of the items in your closet that you wear when it gets really cold outside.
  2. Go for suede or plain leather, i.e. stay away from patent leather or even pleather. Plain leather is best to keep clean and neat, and it is less vulnerable to water and wet snow than suede. Suede is a nice alternative to plain leather in regions with dry cold winters.
  3. Go for a wide toe box to get the most comfortable over the knee boots. Also when buying a pair consider to go half a size up so you can wear a pair of extra socks inside. Best is to try the shoes on with the extra socks. A comfortable toe box is one of the secrets for warm feet at extreme frigid temperatures. Squeezed toes mean cold toes. You will never look stylish when your face screams uncomfortable. So bye-bye pointy toe over-the-knee boots!
  4. When you like heels or your office dress-code requires heels, look for a sturdy heel of up to 3 inch (7.5 cm). Thin high heels are hard to walk on when the ground is snowy, slippy or icy. Make sure they have a thick sole that clearly is not a plateau.
  5. The embellishments should match your primary personal style. Take this free online style quiz if you aren’t sure about your primary personal style.
  6. Only wear your over-the-knee boots at below freezing temperatures and with winter clothes. Best at temperatures in the single or negative digits (less than -12oC).
  7. Wear them with casual or classic winter clothes as anything too glam, too lacy or too sexy gets you into rock star, dance or red light district style. You want to avoid all three “styles” as they are never stylish.
  8. Over-the-knee boots look best with wide midi skirts that cover them totally, skinny jeans (see discussed example of a casual outfit) or riding pants. In the case of wide skirts, pair them with a slim/tight sweater or twinset. When pairing the boots with skinnies or riding pants, a chunky sweater or a tight sweater/tailored shirt under a sporty blazer look incredibly stylish.
  9. When pairing over-the-knee boots with mini skirts or short dresses wear opaque tights. Ensure that there is room between the end of the boots and the hemline of more than a hand width.
  10. When wearing OTK boots with cute dresses or skirts the safest way is to go for an A-line or pleated midi version with lining and a thick fabric. Then the height is totally covered and won’t cause 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 over-the-knee boots are a no no for everyone except for women in the aforementioned 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. You have to avoid that your feet and/or knees sweat. Sweat will freeze/evaporate and cause discomfort, once you are back in the cold. Recall you wear these boots to avoid cold feet in frigid temperatures and knees in the first place. This means avoid to create a situation that makes you feel cold.
  13. Always go for a look that clearly says cold season to not look like a rock star on stage or said Vivian.



Step-by-step How I Styled 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 in this post on the history of cable knit sweaters). I finally found a pair of skinny jeans in my size in Fairbanks in a consignment store. Same thing here! They were brand new with the tags still attached! I don’t understand why people buy clothes and then never wear them. Do you?


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 statement leopard necklace for a casual, but polished weekend look


The following look goes for an American West vibe with a suede jacket, sweater and silk scarf. In very casual work environments or creative work environments in the west of the US this look may even work as an outfit for Casual Friday, if such a culture exists at your office.




The look below is a variation of the above styling recipe. The only differences are the scarf and jewelry. In the look above, these 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 statement necklace


The looks 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. It is clear that this outfit is for insulation to stay comfortable, while maintaining 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, statement necklace, Festina watch, striped winter coat (thrift store find), head band, LeatherCoatsEtc gloves and Longchamp satchel



Explained Example of a Work Outfit

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, Dior OTK boots, Arm party: Golden bangle gift from my late mother, enamel bangle gift from my girl friend, Hermes enamel lion bangle, and Tissot stone watch.





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 tiger buckle 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.


I got this pair on eBay a couple of years ago in summer. They were brand new!


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 wool 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 quarts necklace, and cable-knit sweater. Middle: Diamond-leopard print cropped jacket, Pendelton plaid skirt, Longchamp satchel, silk neckerchief and LeatherCoatsEtc gloves. Left: GNW Luxe sweater, unbranded denim jacket, Festina watch, Charhartt gingham shirt, three string pearl necklace, Ray Ban aviator sunglasses, Yves Saint Laurent bag, Hermes collier de chien bangle




My First Over-the-knee Boots

Ever since Julia Roberts wore over-the-knee boots in Pretty Woman, I loved them. My girlfriends and I bought our first pairs right after we saw the movie the first time. We all went for a flat pair as we sort of associated the stiletto heel too much with Vivian’s job on screen. My friend Katherine invested in two pairs, one in silver for going out, and one in brown. I went for a patent leather black as I could dress it up for going out and down with jeans. My other friend got them in red. She always loved to wear loud colors all over her outfit.


You Are Never too Old for a Great Pair of Over-the-knee Boots in Winter

Of course, these over-the-knee boots moved out of my closet long time ago during one of my closet overhauls. For years, I thought I am too old for over-the-knee boots and it would not be age appropriate. Well, I changed my mind about both, being too old and the term age-appropriate. The latter term namely seems that society dictated woman what too wear, while I have come to the point that I want to wear what looks great on me. The former is sort of opposite to being too young for something when I was a kid. I hated it back than. Thus, why should I accept too old now? Don’t allow yourself to thinking you are too old for OTK boots or to think OTK boots aren’t age appropriate. Instead solve the problem by promising yourself to wear what you want.


Conclusions on How to Wear Over-the-knee Boots

The secret is styling OTK boots over 40 with classics like shown in the example outfits. Search for a great pair of over-the-knee boots that are serious. Go for real leather or suede with sturdy heals. This means clearly veer out of Pretty Woman’s territory to look Young and Hip without looking like trying too hard.

Yes, at 40+, you still can wear over-the-knee boots. The boots have to be high quality materials plus classic details like sturdy, and medium high heels. A not too round, not too spiky toe box, and European classic boot colors (brown, tan) are best. Then, all you have to do is to keep your outfit moderate casual or moderate classic, and use sophisticated accessories.


More Sophisticated Looks with Otk Boots

Are you looking for further inspiration how to style the Pretty Woman footwear?


Not convinced yet?

Here is another example outfit with OTK-boots paired with pink and brown for a work outfit.

Do you wear over-the-knee boots? How do you style them?

Stay warm in style! 😉

Photos: G. Kramm

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