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How to Wear Ankle Boots With Skinny Jeans, Leggings, or Shorts – Tips for Older Women

how to wear ankle boots older women over 60

by  Tina Boomerina (Christina Gregoire)

I can show you tips for how to wear ankle boots with leggings, skinny legging jeans, dresses and, possibly, shorts.  Short boots for women are fun and versatile.

ankle booties for women - photo monsoon prshots.comLet me tell you right up front that it is difficult, but not impossible, to pull off shorts (in general) if you are over 40 or 50.  But, I will give you tips on how to do it, anyway.

High Heel Ankle Boots for Women

Let’s start off with a disclaimer. I only wear heels. Unless I’m off to the dog park or on vacation, I’m probably wearing heels, so I know more about stilettos and stacks than flats. And, you should know that the following fashion rules are only guidelines, as there are usually exceptions to every rule. You are the artist of your own wardrobe. Be creative.

Best Ankle Boots for Skinny Jeans and Leggings

I prefer any type of high-heel boot to most high-heel shoes because a boot with the right fit will stabilize my ankle. This makes boots and booties easier to walk in than pumps or high-heel sandals.

How to wear booties with jeans when you're over 40 or 50And, when you are walking on cobbled streets or unfamiliar sidewalks, you want your heel to stay underneath your foot.

In my opinion, ankle boots look great with skinny jeans and leggings, as long as the jeans or leggings are tucked in. Most of the time, your booties should be the same color or the same shade (same darkness) as your jeans or leggings.

And, cropped leggings with booties only look good on women with very long legs.

Most of our fashion faux pas stem from seeing a trend on a tall, catwalk model and thinking it will look good on regular women like you or me. However, most females are neither anorexic nor 6 feet tall.

Older women with ankle boots and short dress photoShort Boots and Boot Cut Jeans

Modern ankle boots were originally designed to be worn under trousers, because most knee-high boots interfere with the silhouette of a woman's pants. So, flat ankle boots and high-heeled ankle boots are perfect when worn with any straight-leg, flared, or boot-cut jeans or trousers.

If your pants are wide enough to fit easily over your boots, you can do whatever feels most comfortable.  However, I prefer the artsy look of skinny jeans tucked into boots.  It's more trendy.

Wearing Ankle Boots With Dresses

It’s a little tricky to wear ankle boots with a short dress, so here are my rules...

(continue reading about ankle boots on page 2)


Tina Boomerina (AKA Christina Gregoire) is a Baby Boomer born at the end of 1952. Her mission is to make the internet a kinder and gentler place for Baby Boomer women around the world. Tina's specialty is fashion for women over 50.

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  1. Karin

    I can't wear ankle boots. They look better on tall women.

  2. Tina


    If you have short legs, like I do, you might like the look of ankle boots if you match the color of the boots to the color of your leggings, pants, or tights. Try that.


    Tina Boomerina

  3. gloria garrett

    I think it's great that someone remembers that we are still alive. I also love the idea that dressing rules are much more relaxed than 40-50 years ago.I discovered leggings about 2 months ago, God they're great! I'm making a pair of palazzo pants, like I had 50 years ago. And I made and wore my first bell bottoms in 50 years.YEAH!

    • Tina-Boomerina


      Not only are we still alive, but we're kicking ash. I wish I could sew. I would make palazzo pants like the ones I wore 50 years ago.

      Rock on Boomer Sistah!


  4. Debbie

    Your advice was great and I like your sense of humor! Thank you so much!

    • Tina-Boomerina


      I'm glad you like my writing. Some people don't understand the humor. It doesn't translate well into other languages... or parts of the country... well, keep reading.

      I hope you don't live in Kansas. For some reason I like to make fun of people from Kansas. I also like to tease my mother. She has a different last name, so no one will ever know, but she's only been online one time and she's afraid of the internet. My brother (almost 60) is the same way.

      I keep telling both of them that not going online is like running from town to town instead of getting in a car and driving.

      Anyway, glad you like the site.


  5. Miaana Beckström

    Models are not anorexic. There is a world of difference between being thin and anorexic. Throwing the word around without regard as you did is both catty towards other women and disrespectful to those who are suffering from the disease.

    • Tina-Boomerina


      Sorry, I wrote this article ages ago and I don't remember what I said. I'll try to find that word and take it out. Is there another word I could use that is not disrespectful but gives the same idea?

      I didn't mean to cause a problem. I was skinny for most of my life and people accused me of being annorexic or an addict and all kinds of horrid things. I was neither one. There's a fine line between humor and horror.



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