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.

  1. Do OTK Boots Have an Age Limit?
    • Why Do Many Women Consider OTK Boots as a No No for Themselves?
    • Over-the-knee Boots Work at Any Age
  2. What Are the Secrets of Wearing Over-the-knee Boots Right?
  3. Step-by-step how I Styled Casual Weekend Looks with OTK boots
  4. Explained Example of a Work Outfit
  5. Photo Inspirations How to Style Otk Boots
  6. My First Over-the-knee Boots
  7. Conclusions on How to Wear Over-the-knee Boots
  8. Find More Sophisticated Looks with Otk Boots


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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 tigh high boots with red light district, or exotic dancers, respectively. They consider this footwear ok for a girls’ night out of our twenty something sisters, if at all. That style is not age appropriate (whatever that is supposed to mean) for who knows whom including our twenty something sis! It is a uniform for those professions, and only appropriate for them. 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?


Dior OTK boots details
Suede Dior otkb



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
Front view of skinnies with cable knit sweater otk boots look described below


style blogger weekend look with over-the-knee boots
Outfit details: 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 (all own) 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.



style over 40 woman in over the knee boots
Outfit details: Orvis suede blazer, LV silk scarf, GNW Luxe sweater, J Brand jeans, Dior suede boots, YSL bag, and Kieselstein Cord belt and buckle (all own)


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.

Change your look with your accessories. #shopyourcloset #slowfashion Click To Tweet


over 50 years old woman wearing a casual winter outfit with over-the-knee boots
Side view of casual look described below


influencer in over the knee boots
Outfit details: Orvis suede blazer, GNW Luxe cashmere wool sweater, J Brand skinnies, Dior over-the-knee boots, silk scarf and statement necklace (all own)


The look below shows how modest the above outfit gets when paired with a coat. When pairing your thigh high footwear with a long coat, they look like a winter look with a skirt or dress.


Classic winter outerwear look with OTK-boots
Outfit details: 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 Kate Moss for Longchamp satchel (all own)


I just read an interesting post on how to wear over-the-knee boots. #agelessstyle Click To Tweet



Explained Example of a Work Outfit

The next couple of photos, I paired my over-the-knee boots with my floral tweet skirt, denim jacket, cashmere sweater and a chambray shirt. When creating this look I used the skirt as the link between the OTK boots and the denim blue. It’s important to also accessorize your outfit in a spohisticated way.

accessories Arm party
Zoom-in on the arm party


style book author over 50 with over-the-knee boots styled for the office
Front view of the outfit idea described below


over 50 years old fashion blogger with knee-length tweed skirt, denim jacket sweater, shirt and OTK boots over-the-knee boots
Details of the look: 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



The long coat does not give away at all that I am wearing over-the-knee boots. It is clear that this outfit is for insulation to stay comfortable, while maintaining style in cold wet weather outfits.

To look stylish when bundled up, I added colors with a cashmere scarf a colleague brought me as a gift from a family visit in China. The hat is a vintage find I made a couple of years ago in a consignment store in Fairbanks.


mature woman looking posh chic in winter outfit with over-the-knee boots
Dior over-the-knee boots with geometric print coat (consignment find), hat (thrifted), geometric print cashmere scarf (gift from colleague), YSL bag, and matching LeatherCoatsEtc suede gloves



Photo Inspirations How to Style Otk Boots

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

When you wear over-the-knee boots the look must scream I am an outfit to stay warm in style in cold weather! Click To Tweet


fashion blogger in plaid blazer, suede thigh high boots, skinnies for Casual Friday
Front view of look described later

over 50 years old woman wearing OTK boots with jeans


fashion blogger over 50 in Casual Friday work outfit with thigh high boots
Outfit details: Burberry plaid blazer, Gucci scarf, J Brand jeans, and tiger buckle croc impress belt



The next photos give some inspirations of how I style my Dior over-the-knee boots in an ageless posh, casual, and work appropriate way. I got this pair on eBay a couple of years ago in summer. They were brand new!


Stylist’s tip: You often can find brand new items on eBay that were gifts, but they did not fit (physically, taste, etc.), and 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.


style book author in otk suede caloches
Business casual: 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


Alaskan fashion blogger in tall boots, shearling coat, headband and orange skirt
Work outfit: Boots rolled down. Unbranded headband, GNW Luxe cashmere wool sweater, gemstone necklace, Gucci scarf, Vittori shearling coat, Max Mara skirt, GNW tight, citrin earrings, LeatherCoatsEtc gloves and Bellorita designer bag


over 50 years old fashion blogger in business casul winter look with tigh high footwear, skinnies and blazer
Casual Friday: J Brand skinnies, Jeanne Pierre sweater, Gucci scarf and G belt, Burberry plaid blazer


#trendsover40 midlife woman wearing a belt for shape in an over-size sweater
Business Casual: Gucci silk scarf, Orvis over-size Irish cable knit sweater belted for shape with Paloma Picasso x belt, Pendleton glen check pleated wool midi skirt, Hermes collier de chien bangle, YSL bag, Dior over-the-knee boots, LeatherCoatsEtc gloves, and beret, and maxi shearling coat worn as a cape
fashion over 50 woman wearing over-the-knee boots with an American West suede blazer
American West way: Orvis suede blazer, J Brand jeans, GNW Luxe sweater, DIY necklace and silk scarf


midlife blogger in a posh outfit corporative office look
Work outfit: Ann Taylor floral tweed skirt, Oliveo button down shirt, statement necklace, Hermes collier de chien bangle, Tissot watch, Longchamp bag and Oliveo cropped blazer


over 50 years old fashion blogger in brown midi skirt, boots and T-shirt, orange top and matching scarf
Office outfit: Gucci scarf, layering top (similar here), unbranded v-neck sweater, Pendleton brown, winter white glen check midi skirt, Festina watch, Hermes collier de chien leather band, Hermes collier de chien bangle


otk-boots styled with a skirt
Weekend: 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


midlife style book author in winter business casual office look with leopard print cardigan, glen check skirt, suede otkb
Winter work style: 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


over 50 years old fashion blogger Nicole in winter outerwear suitable for going to work in tigh-high footwear
Winter outerwear: Diamond-leopard print cropped jacket, Pendelton plaid skirt, Longchamp satchel, silk neckerchief and LeatherCoatsEtc gloves


stylist in over-the-knee boots, bias plaid skirt, oversize cable knit sweater, motorcycle shearling jacket, beret
Weekend casual look: A-line plaid skirt, Marc Andrew shearling motorcycle jacket, Gucci belt, unbranded chunky cable knit sweater, LeatherCoatsEtc gloves, LeatherCoatsEtc wool beret, and 3.1 Philip Lim bag for running errands


over 50 years old fashion blogger in leather dress with otk-boots
Dinner at a friend’s house: Eli Tahari leather sheath with GNW cashmere sweater, LV silk scarf, and 3.1 Philip Lim bag


stylist in pink sweater, brown tigh high boots, brown midi skirt
Business casual: Bias-cut plaid skirt, Landsend mockneck sweater, smoky quartz necklace and bracelet, Gucci belt, GNW tight


style blogger Nicole in Thanksgiving outfit with scarf, sweater, coat and boots in traditional colors
Folded over: Max Mara skirt, GNW tight, GNW Luxe sweater, Gucci scarf, Bellorita bag, Gabrielle shearling coat, head band, Judith Leiber gemstone necklace



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.

You are never too old for a great pair over-the-knee boots in winter. #agelessstyle Click To Tweet Promise yourself to wear what you want. #fiercefashion #fiercestyle Click To Tweet Confidence is part of great style, always remember that. #styleadvice Click To Tweet


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.

Search for a great pair of over-the-knee boots that are the highest quality you can afford. #midlifechic #OTKboots Click To Tweet

Thus, 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.


Find 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? Let me know, I am curious. Use @highlatitudestyle on IG to show me your otk-look.

Stay warm in style! 😉

Photos: G. Kramm

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