11 secrets to look great in over-the-knee boots

Dior OTK boots details

OTK boots have no 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.

Best stylist’s secrets on wearing OTK boots

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.

11 secrets to look great in over the knee boots post banner

  1. Invest in your over-the-knee boots when you live in a region with cold winter climate. Get the highest quality you can afford in a neutral color of your wardrobe.
  2. 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. A wide toe box is a must. 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.
  5. The embellishments should match your personal style.

    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)
  6. Only wear your over-the-knee boots at below freezing temperatures and with winter clothes.
  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. Only wear your over-the-knee boots outside and 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 to not to create a situation that makes you feel cold.
  11. Always go for a look that clear says cold season to not look like a rock star on stage or said Vivian.

Styling inspirations for over-the-knee boots

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!

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.

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 Business casual: 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)

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)

How I styled a casual weekend look 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

Dior over-the-knee boots #advancedstyle

#over40fashion 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

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Photos: G. Kramm

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