Skip to content

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

#over40fashion #fashionover50 How to style over-the-knee boots: example plaid skirt for work in the weekly Ageless Style series @ High Latitude Style @

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 should not style them like Vivian in Pretty Women.

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

Styling of over-the-knee boots that works

  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.
  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.
  8. Over-the-knee boots look best with wide midi skirts that cover them totally, skinny jeans 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 stay warm 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 over-the-knee boots in a posh or casual, but ageless style.

#over40fashion woman wearing over-the-knee boots Dior over-the-knee boots styled with J Brand skinny jeans, Orvis chunky Irish cable-knit sweater and statement necklace (all own) for a casual ageless weekend look#fashionover50 woman wearing over-the-knee boots with an American West suede blazer Dior over-the-knee boots in an American West way with Orvis suede blazer, J Brand jeans, GNW Luxe sweater and silk scarf (all own)

#over40style woman wearing over-the-knee boots with a floral tweed skirt Dior over-the-knee boots styled with Ann Taylor floral tweed skirt, Oliveo button down shirt, statement necklace, Longchamp bag and Oliveo cropped blazer (all own) for an office appropriate winter look

#maturefashion woman in over-the-knee boots and skirt weekend look Dior OTK boots styled in a casual way with a skirt, Marc Aurel sherling motorcycle jacket, Gucci belt, chunky cable knit sweater, gloves, wool beret, and 3.1 Philip Lim bag (all own) for running errands on the weekend
#over50style mature woman in leather work outfit with OTK boots Eli Tahari leather sheath with GNW cashmere sweater, LV silk scarf, Dior over-the-knee boots, and 3.1 Philip Lim bag (all own)#styleover50 woman in workout fit with OTK boots Dior OTK boots with a bias-cut plaid skirt, GNW sweater, Gucci belt, GNW tight (all own) for a work outfit

When you liked this post, let your friends know how to wear over-the-knee boots when you are over 40.

Would you wear over-the-knee boots over 40? Do you wear OTK boots? What are your style challenges? Let me know by email so I can help you.

Get the support, motivation, and tips to look to your best in life. Get a subscription to High Latitude Style. Deep inside you know when I can do it you can do it too.

Photos: G. Kramm (2015)

Copyright 2013-2016 Nicole Mölders | All rights reserved

%d bloggers like this: