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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 about how to wear ankle boots with leggings, jeggings, skinny 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.

Note: This article has been updated to reflect changing fashion trends.

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 high heels, so I know more about stilettos and stacks and platforms and blocks and kittens and wedges than I do about flats. The last time I wore flat ankle boots was during new wave (1980s), when Oingo Boingo was on the radio and I was pregnant. But, even though most of my experience is with high-heel ankle boots and short-heel ankle boots, the same rules should apply.

Important: "Rule" is probably the wrong word. 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.

Most Women Tuck Their Jeans into their Boots

In my opinion, ankle boots look fabulous with skinny jeans and leggings, as long as the jeans or leggings are tucked into the ankle boot. That's how I wear this look.

read tips about ankle boots

How to Wear Ankle Boots

However, things have changed since I wrote this article way back in 2011. These days, many fashionable chicks... dare I say chic hipster chicks with excellent taste... are wearing their skinny jeans a tiny bit shorter by rolling up the hem about half an inch or maybe an inch.


I have a feeling I should take the word hipster out of this article, because some people don't like being labeled with that classification. I like the word "hipster". To me, it just means a person who is hip to the current, modern trends worn by the hippest of hip people. I know hipster describes a specific fashion and lifestyle... but... the word hipster just rolls off the tongue and makes me smile.

Someday I will try to explain the hipster style as I see it.

Rolled up Jeans Are Not Tucked into Ankle Boots

If you are wearing cropped pants or rolled-up (cuffed) jeans, you will not be able to tuck your trousers into your booties. Trendy women are wearing ankle boots and skinny jeans with a small gap between the pants and the boots. I don't do that, but it is not wrong to wear your jeans and boots in this manner.

For most of you, your booties should be the same color or the same shade (same darkness) as your jeans or leggings. That's what I usually do because I have short legs, and this gives the leg a long, unbroken line. And, in my opinion, cropped pants with ankle boots only look good on women with very long legs. (I don't mean a gap of half an inch, I mean short crops.)

Not Everyone Can Wear Catwalk Styles

Most of our fashion faux pas stem from seeing a trend on a tall, catwalk model and thinking it will look good on a regular woman like you or me. However, most females are not anorexic and 6 feet tall.

Short Boots and Boot Cut Jeans

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

read about ankle boots fashion tips

Ankle Boots Are Fun & Sexy

How to Wear Ankle Boots With Dresses

It’s a little tricky to wear ankle boots with a short dress, so here are my rules. If you are over 40 or 45, you'll probably want to follow these rules at first. After you get into the look, you can try other things.

  • Dark legs look best with dark booties. Bare legs look best with nude booties. There are exceptions, but these are the rules. Once you get the balance down, you can break the rules to go with your mood.
  • This is the wrong way to wear ankle boots. Ellen Page should wear a dress with a flared skirt to balance her shoulders. And, these dark booties look strange with that dress. Light brown boots would be better, although Ms Page would look beautiful wearing a trash bag.

Can You Wear Ankle Boots With Shorts?

Normally, I would snicker if I ever saw a female wearing ankle boots with shorts, but I have seen teens wearing shorts with chunky-heeled boots and they pulled it off.

read about wearing ankle boots

Pattern Socks

Call it hipster style, call it festival style, or call it hot pants redux, but whatever you want to call it, outfits involving shorts are more prevalent now than when I first wrote this article.

For ladies over 40, you can wear city shorts in place of a short skirt, although you should avoid regular shorts (and denim cut-offs) once you reach true "adulthood". I don't care how hot it gets. And, if you ever wear stilettos with shorts, your friendly neighborhood hookers will stop and tell you that you have no taste.

Update: Yes, it's fine for all of you young hipsters to wear cut-off jean shorts. Just don't let your moms borrow them.

Maxi Skirts With Ankle Booties

black ankle boots for women - photo hobbs prshots.comBoth flat and high-heeled ankle boots are great with long skirts. I believe you should wear tights to match the boots, if the boots are dark, because when you sit down more of your leg will show. One alternative would be to wear cute funky socks with a Fair Isle (Nordic) or repeating pattern. People would only get a glimpse of this chic little detail.

My new favorite thing is to wear my ankle boots with funky patterned socks, but I scrunch the socks down so they hardly show... like just an inch or two. Very fun. I'm losing it in my old age, but I'm losing it in a subtle way that doesn't make people want to run away from me.

Cuffed Ankle Boots

Cuffed booties can be worn with leggings, skirts, and shorts. The most important thing with cuffs is that you must be able to see the contrast of the wide cuff against the skinny leg. Cuffed boots are only cute if your skinny leg (or covered skinny leg) shows. Without that, your ankle boots will appear clunky.

For an easy no-brainer, tuck your skinny jeans into your cuffed boots. I think that cuffed boots are super sexy if they are done right. And, some cuffed boots look better if they contrast with the jeans or leggings.

ankle boots for women over 50Ankle Bootie Outfits

All women should start their own fashion experiments in front of their mirrors and try their boots in new ways. I started wearing black suede booties with black tights in 1997. I remember this because '97 was an important year for me, and I remember my girlfriend saying, “I didn’t know you could wear ankle boots with a mini skirt.” Right. Like I needed permission to wear my own clothes.

Any woman can look amazing in ankle booties, but every woman looks best in her own adaptation. When you get a pair of booties, try them on with everything you own. As long as you have a full-length mirror, you will be able to tell what works best with your type of body.

More Articles for Hip Baby Boomer Women:

How to Wear Leggings if You're Over 40 or 50

Women's Travel Cruise Wear Online: Chicks Over 40 or 50

23 Trendy Pluse Size Clothing Sites for Large Women Sizes 1x - 12x

Women's Packable Raincoats and Jackets for Travel

Photo Credits: prshots.com.

  • Main Photo: I lost the list for these boots when we updated the site.
  • Wedge Ankle Boots: Monsoon.
  • How to Wear Ankle Boots With Skinny Jeans: Monsoon.
  • How to Wear Ankle Boots: Miss Self ridge.
  • Ankle Boots Are Fun & Sexy: Apricot, Phase Eight, East.
  • Pattern Socks: White  Stuff.
  • Short High Heeled Boots: Hobbs.
  • How to Wear Ankle Boots: La Redoute.com.

What Do You Think of this article? Leave a comment at the bottom of the page. I need to write an article about cuffed jeans... someday... but I'll have to study younger women because I don't wear that style.

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.


    • Tina-Boomerina


      Okay, I got rid of the word anorexic. I hope you are not a hipster who is going to give me shit for saying something wrong about hipsters.

      Do you really think I was trying to make fun of women who are killing themselves by starving their bodies? It's just the way I am... catty and disrespectful... in a nice way.

      If I were politically correct, I would be as boring as all the other bloggers are. Is that what you want?

      Well, come back anytime and bitch about something else soon, because that's how I know there really ARE people out there who are reading my blog.


      • Tina-Boomerina

        Oh fukkit. The sentence didn't sound right. I changed it back.


        • Tina-Boomerina

          And, I shouldn't say that all the other bloggers are boring. Some are good. You'll know which ones they are when you're reading their blog while drinking a soda and the Coke snorts OUT of your nose.

        • Sybil

          Three words: I love you!
          People are so afraid of fallout that even humour has become taboo.

          • Tina-Boomerina


            OMG, I love you back! It's so true. I don't think people can tell the difference between humour and hatred.

            I'm just trying to lighten up people's day, while explaining the meaning of life... and whatever else pops into my head.

            Come back often. Leave encouraging comments. You are fabulous.


  6. Fiona

    Love this article.

    How do I follow on FB and how do I join site?
    I can see log on but don't have password etc.

    Any help would be great.


    • Tina-Boomerina


      I've been having technical issues lately, but I'm going to be starting a new FB page and find better ways to keep the conversations going. I'd love to build a forum, but I don't have time right now.

      The log in button is for authors. I don't have a feed anymore because it seemed to go directly to scrapers. Scrapers are people who copy articles without permission and screw over writers by stealing their audiences. Scrapers make money by diverting a large percentage of the small income that bloggers get from advertisements. Scrapers are $#&^&!%^^&&*+^* asswhipe ^*#*%@!%$^*&s from hell.

      When I get my act together, if ever, I'll start up my newsletter once again.

      Tina Boomerina

  7. Daniela Scott

    I have high arches and am very picky about shoes. Ankle Boots are the best! These are so comfortable. I love them! Great stylish shoe!

    • Tina-Boomerina


      I love ankle boots. I like the extra stability that I get with boots if they fit right in the ankles. Boots and booties ROCK! I'm glad you told me another reason to love boots.


  8. Sarah

    Love your humor, love your blog! Thank you for keeping it real...so many people lose authenticity by trying to be so PC. I am in my 30's but feel more comfortable dressing in a classic and classy way (which it seems only 'older' women do anymore), so your blog and helpful tips are so much appreciated! Hugs to you!!

    • Tina-Boomerina


      Thanks so much. We've just made you an honorary Boomerina.

      I was born before PC, so I don't give a freak (most days). Glad you like our style. I'm also glad you're (probably) not wearing dresses so short we can see your undies even before you bend over.



      • Karen Brorsen

        I think you are fabulous and so straight to the point! Just the way I talk .... and people either love it or have no idea how to take me! Thank you for staying it out loud!!

  9. Tina-Boomerina

    ps well, i shouldn't assume anything these days...

  10. Pamela

    Why can't you place photos of 30,40,and 50-something women in an article about said ages?! This is no help when all I see are 25 year old models who weight 125 lbs (including their boots!) and are 6'5" tall!

    • Tina-Boomerina


      I agree.

      I would love to replace photos of 30, 40, and 50-something women with older models. Read this to find out why I use photos of anorexic 12 year olds. http://www.boomerinas.com/2013/10/21/why-use-young-swimsuit-models-for-baby-boomer-articles/


      • Tina-Boomerina

        PS. I doubt they are 25 years old. They are more like 12... ok.... maybe 15.

        AND, I love that you say they are 125lbs including their boots. Yes... maybe... if their boots are 10lbs. I totally agree with you, but I don't have enough time and money to find good models and the right clothing for my articles. I hope you read the link directly above, which explains the problem.

        I WISH I could find better photos. Sometimes I use my own photos but they seldom come out clear enough or good enough to show you the trend I'm talking about. I could use NO photos but I think that would be worse.

        • Pamela

          Tina, I'm impressed you responded. Frankly, just thought I was venting to the air! Okay, so I obviously know absolutely nothing about models. You understood my main point, though...I was simply wanting to know how to wear the current styles without looking ridiculous. I encourage you to follow through with photography appropriate to your message. It wouldn't be easy, I hear that. However, I think you would grab your audience's attention (like a good lead...) in the sincerity of the final work. I can say this because I AM over 50. ;) Thank you for the response!