13  secrets of a stunning over-the-knee boots look (ultimate guide)

Over-the-knee boots keep the knees warm. This post is your ultimate guide how you can wear OTK boots over 50 and look effortlessly stylish.

Contents
  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. Photo inspirations how to style over-the-knee boots
    • Step-by-step how I styled casual weekend 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 (own)

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. When wearing a wide skirt go with a slim/tight sweater or twinset. When pairing the boots with skinnies or riding pants go for a chunky sweater 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. 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.

Don’t let the right outfit be a random thing. Wear the right look in every situation by looking up what to wear when in How to Dress for Success in Midlife. Buy my book now.

Photo inspirations how to style over-the-knee 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

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 pearlnecklace, Ray Ban aviator sunglasses, Yves Saint Laurent bag, Hermes collier de chien bangle (all own)

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 (all own)

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 (all own)midlife woman wearing a belt for shape in an over-size sweater with OTKB Winter 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, LeatherCoatsEtc gloves and beret and Vittari maxi shearling coat worn as a cape (all own)

fashion over 50 woman wearing over-the-knee boots with an American West suede blazerAmerican West way: Orvis suede blazer, J Brand jeans, GNW Luxe sweater, DIY necklace and silk scarf (all own)

style over 40 woman in over-the-knee boots with floral tweed skirt 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 (all own)

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 (all own)

okt-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 (all own)

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 (all own)

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 (all own)

mature fashion woman in over-the-knee boots and skirt weekend lookWeekend 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 (all own) for running errands on the weekend

mature woman in leather work outfit 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 (all own)

style over 50 woman in workout fit with OTK boots Business casual: Bias-cut plaid skirt, Landsend mockneck sweater, smoky quartz necklace and bracelet, Gucci belt, GNW tight (all own)

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, gemstone statement necklace (all own)

Like these outfit ideas? If so, please feel free to pin them to your own Pinterest board.

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

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 for Casual Friday, if such a culture exists.

fashion blogger over 50 in Casual Friday work outfit with otk boots

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 Click To Tweet

over 50 years old woman wearing a casual winter outfit with over-the-knee boots

fashion accessories

woman looking in style 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 (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

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! 😉

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Photos: G. Kramm

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