Over-the-knee boots have a wrong reputation

Do you remember the movie “Pretty Woman?” I loved Julia Roberts‘ over-the-knee boots she was wearing in the movie. When I was in my 20s, I used to have a pair of flat over-the-knee boot in black patent material. I wore them with my leggings suit, or over skinny jeans with a wide sweater. My husband never liked the boots because of “Pretty Woman”. Nevertheless, I wore them literally nearly until they fell apart. My girl friend had the same pair, but in silver. She styled them with mini skirts. So how can babyboomers and gen X wear over-the-knee boots and look serious? This post provides several suggestions how to wear otk-boots over 50 and not look like Pretty Woman.

fashion blogger in work outfit with over-the-knee boots
Ann Taylor floral tweed skirt with Oliveo faux suede jacket, Oliveo chambray shirt, Dior over-the-knee boots, and Kate Moss for Longchamp bag (all own)

At what age should you stop wearing otk-boots?

You can wear over-the-knee boots at any age if you style them posh. I did not own a pair of over-the-knee boots for quite a while, probably because you can more easily get away with them, when you are in your 20s than at any time thereafter. I also admit the fact played a role that my husband never liked the pair I had early in our marriage. One day last winter, when we went to a milonga on a 40 below zero (-40oC) day, a dance friend in her 50s wore over-the-knee boots. She did look very stylish, and not “Pretty Woman” at all! After the dance, we sat in the car idling for 15 minutes  to warm up the engine, and to be able to put in the reverse gear. I got cold knees, and mentioned Flor’s great looking over-the-knee boots to my husband. He totally agreed that well styled with the right over-the-knee boots, the over-the-knee boot look is far away from being “Pretty Woman”. Thus, on this evening, I decided that I will look for a pair so I would not get cold knees in winter again when idling the car in a parking lot for 15 minutes.

stylist showing how to look mature with over-the-knee boots
Ann Taylor floral tweed skirt, Oliveo blazer, Dior over-the-knee boots and Kate Moss for Longchamp bag (all own)

Buy off-season for a great deal on a high quality

This summer, I started looking for over-the-knee boots. At the end of summer, I was lucky to get this pair of Dior over-the-knee boots for a quite good a steal on eBay. Even though temperatures are still about 75 degrees away from 40 below zero (-40oC), I tried them out as I could not wait any longer to wear them. This work outfit does not look like “Pretty Woman” at all, but makes every woman pretty. 😉

Do you like otk-boots? Do you own a pair? How do you style them? Let me, I am curious.

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Photos: G. Kramm

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