Thigh High & Over the Knee Boots-Could You? Should You?
I received an email tod
ay asking the following question:
“I’m working on my Fall 2009 wardrobe, and love everything I’m seeing in the magazines. What is your take on the “over-the-knee” boots that seem to be everywhere? How would you suggest a 40-something woman wear them and not look ridiculous? (or is that not possible… )”
My first thought was welllll…. My next thought was, “great question”. So what’s the answer? As you have come to read in my blogs, nothing is ever as easy as a yes or no, black or white. This is definitely a younger look.
Let me ask you this:
- Where do you live (metro, surburban, rural)
- How old are you?
- What is you core style (do you have a dramatic style?)
- Where are you planning on wearing them?
Now, I’ll give you my answers to the above questions.
- If you live in a major metropolitan area (think big City) you might be able to wear the thigh high or over the knee boots while out at night or shopping with friends,but NOT to work.
- If you are pushing 40 or over 40, then think again. After a certain age it is very difficult to carry off a look that is as extreme as the “dominatrix” look without looking foolish. Leave these looks to the 20-somethings that can risk the opportunity of making.
- Is your “core” style Dramatic? This is not as “trendy” as it may seem. This look pushes the edge and requires all the accoutrements that belong with this look. Dramatic makeup, dramatic colors, leather, etc. In the photo below Kate Moss has successfully carried it off, but look at how she has paired it with other pieces. (oversized glasses & bag, large scarf, bold sweater) (Get the picture-oversize, bold, large, etc.) If you can’t successfully work the entire look you’d better leave it alone.
- Where are you planning on wearing this look? To work, to school, out on a date, dancing? This definitely doesn’t project a successful business image so don’t try to make it look like one. You will miss the boat if you try. Missing the boat will make you look like a fashion disaster.

As a last comment, when you see new fashions in the magazines, take a look at how they are staged. Look at the styling and the clothes that are combined with the look. Look at the lighting of the photo shoot, look at the background. For this look you will most likely see Hollywood types, runway shots and extreme locations to support the overall feeling of dominatrix.
The legs get a lot of attention. Tights or jeans, the leg is accentated. So, if you don’t have great legs, even if you are 20 something, run away from this look.
So, here’s my final answer: “If you are 40’sh, have great legs, can pull off the entire look, want to wear it out on the town or shopping in the city, I say you go girl”. I’ll be leaving this one alone!
To learn more about adapting the latest trends to your own style click on the following link. Adapting Trends to Your Wardrobe
“Look good, feel great and have fun doing it!”




August 17th, 2009 at 2:38 pm
Great post Karen, thank you! I like the Kate Moss look on the far right the best, but I think I like them a little bit less knowing they are called DOMINATRIX boots! Not sure where that fits in with my overall CLASSIC style.
~ I’ll have to hit the Saks shoe department this week; maybe just trying them on will alleviate my desire for these boots and I can see firsthand in the mirror how ridiculous I look.
October 18th, 2009 at 11:34 pm
Really enjoying reading your breakdown of this trend and your blog in general. Keep it up!