Tasteful Ways to Wear Over the Knee Boots After 40

Over the knee boots have gone from being a little bit edgy a few years ago and pretty mainstream. Flat or low heeled knee boots look fabulous with your favorite sweater and jeans, and you can even wear higher knee boots with skirts and dresses at any age, so long as you follow a few guidelines.

Here are some tips to keep in mind when you are over 40, 50, or more, and you want to make sure you look tasteful, not trashy.

How to Wear Over the Knee Bots |Brown leather over the knee boots with a rust sweater and booties

1. Try Low-Heeled Over the Knee Boots

If you’re dying to give over the knee boots ago, but you’re nervous about looking silly, don’t be. A very safe bet is an over the knee boot with a low or flat heel. Here’s why the flat heel balances out the boot’s tallness and softens the super sexy message these boots send. Instead, you come across as casually chic.

Black suede over the knee boots for women worn with an off the shoulder sweater and jeans

Suede has a slightly more casual feel than leather, so a suede over the knee boot is a great starting place. Pair your boots with skinny jeans or leggings. If your legs are on the short side, you may want to go with black suede boots worn with black pants or leggings. That will lengthen your legs. The suede adds some nice texture, which ensures that black on black isn’t boring. If you are not concerned about your leg length, go for a contrasting boot like brown or merlot, or even navy has been popular.

How to wear over the knee boots |dark brown over the knee boots sweaterdress and faux fur vest

2. Don’t Show Much Leg

Many young gals are wearing short, flirty mini dresses with very high over the knee boots, and it looks cute for that age group, but it can really look like you are playing little girl dress-up if you try to pull this off when you are a mature woman. Dresses worn with over the knee boots look best when the dress is too short, too skimpy, or too fussy. The key to pulling off a dress with over the knee boots is to show a hint of leg and keep the rest of the look covered up. Your boots should almost meet your hemline.

3. Pair with a Sweater Dress

A sweater dress is a great example of a dress that looks fab with over the knee boots. Again, it’s about balance. This dress is short enough to show off the boot, but it isn’t a mini. It is a simple, clean-lined, modest style that lets the boot have all the attention, and it is a nice heavy knit which gives a casual feel to balance out the sexy boot.

How to wear over the knee boots |taupe, suede over the knee boots, leggings and colorblocked sweater outfit

4. Get the Proportions Right

This is a popular style recipe that works at any age. Take a chunky, oversized sweater and wear it with jeans or leggings and over the knee boots. It’s a youthful, figure-flattering look.

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7 thoughts on “Tasteful Ways to Wear Over the Knee Boots After 40

  1. I just love this look but at only 5’2” I don’t think I could pull it off. They should make boots that vary according to height! Lol. I’ll keep wishing.

  2. I bought OTK boots in black, taupe, navy, and chocolate suede. Love them all and have worn the blue and black TO DEATH already this year. Now I need to focus on the taupe and chocolate. So sexy — and warm, and comfortable! They are my new favorite things I bought this year I think.

  3. This really is excellent advice about wearing these kinds of boots. I do all three of these when wearing mine and I am very tall at 6 feet with very long legs…and it always looks stylish and tasteful rather than smutty.

  4. I have yet to see over the knee boots popular in CO. They’re in all the stores. Maybe the younger set wear them. I like the look.

  5. Purchased a pair of flat heel, olive, suede OTK boots months ago and have yet to wear them. Glad to see I nailed the selection. Thanks for the post.

  6. I needed new flat black boots this winter, so I chose black suede OTK boots. I haven’t worn them with a sweater dress yet, but plan to, I have only worn them with skinnies. They are fabulous, but I fear they will be extremely dated next winter, so I plan on wearing them as often as I can. I love them, they are comfy and warm, and look fabulous! I love these boots!

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