How to wear over-the-knee boots right over 40

Over-the-knee boots work at any age

Over-the-knee boots are age appropriate 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.

Why do many mature 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 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.

The secrets of wearing over-the-knee boots right

Here are my tips how to look timeless and appropriate in over-the-knee boots and feel comfortable wearing them at any age:

1. 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.
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.
4. Avoid pairs with pointy toes. They squeeze your toes which is a recipe for cold feet!
5. Make sure they have a sturdy, not too high heel and a thick sole that clearly is not a plateau
6. The embellishments should match your primary personal style. Take this free online style quiz if you aren’t sure about your primary personal style.
7. Only wear them at below freezing temperatures, best at temperatures in the single or negative digits (less than -12^oC).
8. Wear them with casual or classic clothes, i.e. steer clear away from anything glam, lacy or too sexy.
9. 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.
10. 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.
11. Only wear them outside and switch to pumps or other work appropriate shoes when you arrive at the office. You don’t want to sweat in the boots, no matter how tall they are. The sweat would freeze or evaporate once you get outside and would result in what you wanted to avoid in the first place: Cold feet and knees.

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.

Example and details on how to style over-the-knee boots

When styling your OTK-boots, your goal is to create a mature, powerful and serious look. The photos above of my OOTD with my over-the-knee boots and zoom-ins on details of the styling are an detailed illustration of how to get it right. In plain English,

Here are some further OTK boots outfit ideas for women over 40.

Dior footwear styled with Gucci scarf, layering top, Pendleton pleated glen check skirt, Festina watch, Hermes collier de chien leather band(all own) Dior over-the-knee boots styled for Casual Friday with J Brand skinnies, Jeanne Pierre sweater, Gucci scarf and G belt, Burberry plaid blazer (all own)

Dior over-the-knee boots styled with 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)

Dior galottes worn with 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) Dior suede boots styled with 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)

Dior tigh-high footwear worn with diamond-leopard print cropped jacket, Pendelton plaid skirt, Longchamp satchel, silk neckerchief and LeatherCoatsEtc gloves (all own)

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

You can find further examples and styling inspirations for OTK boots worn with a a cable-knit sweater and a skirt.

Do you wear over-the-knee boots? How do you style them? Let me know, I am curious.

Stay warm in style! 😉

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Photos: G. Kramm

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