Can you Wear Ankle Boots with a Skirt?

Ankle Boots for Women over 50

Can you Wear Ankle Boots with a Skirt?

Quote of the day: “Make the most of yourself, for that is all there is of you.”  – Ralph Waldo Emerson

This could be the rule that you heard growing up—never break up the line of your leg if you want to appear taller. And, to be truthful, there were many comments on Sixty + Me’s Facebook page regarding this characteristic about ankle boots!

And I do understand the thought about trying to appear more vertical. But I also think some women can be a little rigid in those “rules” they learned so long ago. I like the idea I hear from other bloggers about having fun with their clothing and using it to express their personality! If you missed the other ways we wore our booties, check them out with jeans, here, & with shorter trousers, here. It’s been so fun working with Eve & Sheela on this subject—don’t forget to click over to their sites!!

But let’s talk functionality about this concept of wearing your ankle boots with a dress or skirt. Since it’s officially autumn, the weather can be bipolar. And what’s a better way of counteracting the cool mornings and warm afternoons than by covering up the tootsies while leaving your legs exposed? But you may have a different idea? Let me know in the comments below!

Eve of The World According to Eve: Sometimes dresses can be the easiest piece of clothing ever! Just throw it on with footwear and you’re good to go. This outfit reminds me of the yin/yang I love! The dress is sweet with polka dots and flowers while the ankle boots are more boho with fringe!


Sheela of Sheela Writes: Here is the queen of print mixing—channeling the camo again! I love how the hat & booties bookend with the burgundy color—it’s a great recipe for fabulousness!


Dress – Dezzal~~Camo Bomber Jacket – StitchFix~~Hat – a gift from Eve~~Ankle Booties – GX by Gwen Stefani

Jodie’s (50’s) Outfit: I have to confess that I went out of my comfort zone when creating this outfit. I originally was going to wear my chambray (solid colored) dress, but then decided to be more brave with this print dress.

Fashion for women ages 50 and older.

I added the pin on the scarf to hold it in place, but I didn’t want it to be a focal point. So I picked out this pink fish pin, that is almost hiding!! It’s more like a surprise when you look closely!

Fashion for women ages 50 and older.

I just painted these earrings with nail polish. They were a darker metal and therefore you really couldn’t see them against my hair color. I figured some light pink nail polish would work and then I added a darker purple around the edges!

Fashion for women ages 50 and older.


Fashion for women ages 50 and older.

Dress: Peach Love from Blue Clover (here)~~Sweater: Sport Tempo(similar here)~~Boots: Sam Edelman (here)~~Scarf: (similar here the skinny version)~~Pin: (similar here couldn’t find a pink one)~~Earrings: (similar here)~~Purse: Charming Charlies (similar here in a light pink)

Nancy’s (60’s) Outfit: For Nancy, we pulled out her white dress! It could be a great way to get more use out of a summery dress for the fall months!

Fashion for women ages 50 and older.

We added a black & white jacket to keep Nancy warm and threw in some tassel necklaces!

Fashion for women ages 50 and older.

I thought the brown earrings would pull in the brown from the ankle boots.

Fashion for women ages 50 and older.

Nancy wore this same dress for our White Dress series here, here & here if you missed it!

Ankle Boots and Skirts for Women

Dress: Xhileration (similar here not as flared)~~Jacket: Charming Charlies (similar here)~~Boots: Impo (similar here)~~Necklace: (similar here the burgundy version)~~Earrings: (similar here)~~Bracelet: (similar here)

Charlotte’s (70’s) Outfit: I figured since mom’s ankle boots were neutral, then I was going to add in some print for the top half of her body!

Fashion for women ages 50 and older.

There were a couple reasons I left off a necklace. The print of the duster is big and colorful. We had her wear a belt. And there are scallops at the neckline of her shirt. I figured all of these elements were enough without a necklace.

Fashion for women ages 50 and older.

Fashion for women ages 50 and older.

Both the skirt and duster my mom made on her sewing machine many years ago! The skirt is a blush pink, but it can really look neutral when paired with certain colors.

Fashion for women ages 50 and older

Fashion for women ages 50 and older.

Skirt: Mom made it (similar here in one size only)~~Jacket: Mom made it (similar here with leather trim)~~Top: Sara Stephen (similar here)~~Boots: Hillard & Hanson (similar here in a suede)~~Belt: (similar here)~~Earrings: (similar here in a tassel form)

It’s been so much fun styling different items!! Thanks for joining us on this journey!

The Facts

Even if you wouldn’t consider purchasing your clothing online, it can be helpful to look through my links to see what is available! It certainly doesn’t hurt my feelings, if you click on them but don’t like them. Just so you know, one of the ways I make money from this blog is through these linked items.

Keeping in Touch

Are you registered for my email reminders to let you know when a post goes live? I’d certainly love it if you take the time to sign up and make sure all your friends sign up too!! There are other ways to follow my blog. Facebook readers can see my posts by liking my page. Or my Pinterest page has all of our outfits in a nutshell! Then there’s also Instagram! I’m really trying to grow this platform, so if you’re on it, I’d appreciate the follow!

And if you’re new to the party, you can always see our outfits organized by categories, here! Don’t forget to check out the deals & discounts too, on this page!

And here’s a collection of ankle boots for those of you willing to try a different color than black!

  • Kathleen McDermott

    Yes to ankle boots with skirts and dresses. All cute looks above. Yours is my favorite.

    • Thanks Kathleen!! For some reason I have been absolutely loving the ankle boots with shirts & dresses lately!! It just seems so modern!

      • Kathleen McDermott

        I found patterned ankle boots like yours (which I’ve been coveting since first seeing) on TJM online! Oh happy day! I immediately put them in my cart and stupidly (and uncharacteristically) waited to purchase. They sold out pronto. “Shoulda bought it when I saw it” I’m kicking myself.

        • Kathleen McDermott

          And yes! The look is modern and fresh.

        • Ughhhh!! But I bet you’ll find another pair this fall!!

  • all three looks are fantastic examples of how to create different balances of color and pattern into unique and stylish looks. Jodie, your boots are fabulous but it’s your mother’s outfit that is the standout in this post. You are a wizard. Thanks for linking with Fine-Whatever.


    • Jodie Filogomo

      Thanks so much Rena—my mom will be tickled pink that you said that!!

  • Somehow I missed this post. Y’all are seriously rocking these booties! Each one of you look beyond fabulous. Good for you for pushing your comfort zone because it is so fun and colorful! I Love a dress and bootie combination, even though I am a shortie. 🙂

    • Jodie Filogomo

      I think this is my new favorite way to wear them—maybe because it is breaking the rules? I’m a shortie too!!
      In fact I just wore different ankle boots on Monday with a dress to the movies with girlfriends—and even one of my girlfriends was styling hers that way!!

  • sue

    I love ankle boots Jodie and you all look fabulous. Thanks for sharing at Over the Moon and have a beautiful day.

    • Jodie Filogomo

      Thanks for the kind words Sue!!

  • I am wearing this styling as I type this! I love ankle booties with dresses, especially for this transitional weather

    • Jodie Filogomo

      I really have fallen in love with this combo—I wore it to a movie on Monday night with girlfriends. And even another one of the girls had it on (from reading my blog —isn’t that cute?) —because we are all about the same age!!

  • Melissa

    You ladies are always looking fab!! Love the pin of your scarf, cute detail!!
    Nancy white dress is soooo lovely the way she styled it.
    Thank you for linking up with Weekend Wear


    • Jodie Filogomo

      Thanks so much Melissa for the kind words!!
      I love Nancy’s dress—and the best thing is that it was under $15!! I think she can wear it much more than she imagined!!

  • PetiteOver40

    You hip ladies with all your patterns and colors and adorableness!!! I’m definitely down with booties paired with dresses/skirts these days. They really make a lot of sense for this transitional weather–and when you style them the way you all have them styled, it’s easy to see how they make fashion sense too!

    Hugs, 💙

    • Jodie Filogomo

      I’m even wearing some black ankle boots with a dress today—our book club is going to see the movie Girl on a Train since we read it last year!! They are a fun, stylish group of women, so I have to keep up with them!!

  • Brilliant styling!!!!

    – Lily Kanaya

    • Jodie Filogomo

      Thanks so much Lily!!

  • Anna Marcus

    Jodie, my favourite pieces here are your gorgeous boots and your mom’s duster. I am surprised you haven’t stolen it from her yet

    • Jodie Filogomo

      Haha Anna!! I’m only allowed to take mom’s clothes when they are too small for her—she’s sure she’s going to wear everything in her closet otherwise!!
      Thanks for the giggle and the kind words!!

  • Love all of these fall ankle boots! I’ve been searching for cute burgundy ones and these are a great start!

    Chow Down USA

    • Jodie Filogomo

      I’ve seen some great burgundy ones online lately!! That and olive green are definitely the colors of the season!!
      Good luck on your hunt and can’t wait to see what you get!

  • Tessy Onyia

    Oh wow! Jodie now you are making me jealous. this is simply amazing! Your dreeses and ankle book are so cute.

    • Jodie Filogomo

      Tessy—what a cute thing to say!!
      Happy Sunday!!

  • So great on all of you. I’m a huge fan of ankle booties and wear them all Florida winter. I love what you did with your earrings, Jodie! And thanks for linking, xox


    • Jodie Filogomo

      I probably don’t wear my ankle boots as much in the winter because I’m trying to stay warm in the snow—ha ha!
      But it’s nice to have the option!!
      Thanks for the kind words, Patti!

  • Fantastic images

    • Jodie Filogomo

      Thanks Olga!

  • Pam@over50feeling40

    Cute…the boots look fun on all of you!

    • Jodie Filogomo

      Thanks so much Pam!!

  • This is one look I have yet to be able to pull off. You, my friend, have proven it can be done…no matter what age! Well done!!

    • Jodie Filogomo

      I know you can do it too—it might be perfect for your weather especially!!!

  • I love this way of wearing ankle boots, but being only 5’2 I don’t feel that I can get away with it. But as you say Jodie, we have to break our boundaries sometimes so I might have to post about this ! You certainly can’t hide those gorgeous floral boots away now anyway ! I’m totally loving those! x

    • Jodie Filogomo

      I’m only 5’2″ also Laurie! And I know those rules tell us it’s a no-no. But really, in pictures, you can’t tell a person’s height. All we can see is if the proportions and silhouette look good! So I’ve been trying to concentrate more on those details. Besides—it’s be fun to try all the things we aren’t supposed to wear!!
      Thanks for the love!!

  • I think that the rules have changed so much when it comes to fashion! It’s also great to challenge traditional ideas of dress! Great post, as always!

    • Jodie Filogomo

      You’re exactly right Joti. I think it can be harder to challenge some traditional styling “rules” for us older generations. Maybe because we’ve heard the rules over and over for so long.
      But I think it’s important to change it up in order to keep us modern! I mean, we don’t still ride & horse & buggy anymore, right?
      Thanks for stopping by!!

  • First, everyone’s ankle boots are FABULOUS! I’ll take a pair of each! 😉

    Second, I really like the boots with dresses! It’s interesting how easily we get stuck in rules and never really bother to rethink them – ankle boots definitely can work with dresses.

    Third, I love that you went out of your comfort zone with your outfit – it’s great!

    Andrea’s Wellness Notes

    • Jodie Filogomo

      It’s so true what you said Andrea—-we get so comfortable styling pieces in the way we know, that it seems “wrong” to do it any other way. Heck—I’ve totally been guilty of that in the past!
      But seeing others try new things has been so enlightening for me! And even when there are times, I don’t like what I styled, it’s a learning process (and not the end of the world)
      Thanks so much for your kind words!!
      Happy Sunday!

  • In the entire series, Jodie, this is my fave look from you and from Nancy (isn’t that interesting how varied your readers’ opinions are?), and from Charlotte, it was the one with shorter pants. I’m really impressed by how far you took the print journey with this dress, my friend. The little details you incorporated in the brooch and the earrings, everything melding together perfectly. And I’m especially appreciating that you went with a solid (albeit bold) colour for the bag. Perfect. Just perfect. Loads of love, to you, Nancy and Charlotte. With Eve, we could well be the next Angels, eh? 🙂 happy weekend, Jodie xoxo

    • Jodie Filogomo

      It truly is amazing how everyone’s perspective is so different when it comes to style.
      But that’s also what is so wonderful about it really—-individuality is a fact, even though we tend to want to be like others in many things!!
      It’s always such a fun project to see how you and Eve take a category and make it your own—sometimes kinda like I do, and sometimes not!!
      Can’t wait for the next one!!

  • Love the looks! I can wear ankle boots every day!

    • Jodie Filogomo

      I know—we are funny that way, huh? And then after months of cold weather, I so look forward to pulling out my sandals again!!
      Thanks for reading!

  • Jodie, I love your boots and pattern mixing! You all look gorgeous!

    Doused In Pink

    • Jodie Filogomo

      Thanks so much Jill!!
      I am starting to like print mixing more and more!!

  • Amy D. Christensen

    This is my fave of the series too! I love your outfit Jodie. The print of your dress and the print on your booties are so complementary. Plus I love the pop of purple on the sleeves and the pop of pink of your bag. The leopard print pairs well with the stripes on Nancy’s jacket and your Mom is an amazing seamstress. Can’t get over all the things you style on her that she has made. So cool! Great series, Jodie. Keep them coming! – Amy

    • Jodie Filogomo

      I think it could be my fave too!
      Maybe because it’s different than just wearing it with jeans, but i really like the look too!!
      Thanks for all your encouragement Amy!!

  • Versatilestylebytracey

    These are my favorite looks in the series. There really is something fun and spunky about wearing your ankle boots with a dress or a skirt isn’t there?

    • Jodie Filogomo

      Spunky!!! That’s exactly the feeling!!
      Thanks Tracey!

  • I’ve heard the rule about not breaking up the line of your leg, but I have to say, I feel a lot freer and happier wearing whatever the heck I want! It seems we have that in common. As I’m sure you know, I love the look of an ankle bootie with a knee length dress. Yours almost has a mod vibe with the printed shift and bootie. Such a fun, playful, and groovy look!

    <3 Liz

    • Jodie Filogomo

      Thanks Liz—I liked how these looks came out—definitely more fun and adventuresome!!
      And groovy—that word always makes me smile!!

  • GAH!!! I WANT your booties! ; P

    I do feel that your Mom’s neutral almost skin colour booties avoid the whole, “cutting the line of the leg” issue.


    • Jodie Filogomo

      I think that’s why my mom didn’t complain as much when I styled these outfits!!!
      My booties remind me of that pair you didn’t buy—you know, because you have restraint and I don’t!!

  • i’m loving the graphic and prints ankle boots! Very a la mode!


    Tamara –

    • Jodie Filogomo

      Thanks Tamara!!

  • I love ankle boots with a skirt or dress and still feel like they are very flattering to the leg line if you find the right pair. You all look beautiful!

    Amy Ann
    Straight A Style

    • Jodie Filogomo

      You’re right—that probably is a key item—finding the right pair!
      I think that’s why my mom’s booties look good because they basically match her skin.
      I do like Nancy’s because they are fitted to her ankle and aren’t too wide.
      Mine, at least are low cut!
      Whether we look back on these and groan in a couple years—well who cares? It’s fun & creative!!

  • Ankle booties totally add an edgy youthful feel to any look! Love this post and your booties are amazing!

    xx, Elise

    • Jodie Filogomo

      Thanks Elise!

  • Jodie! I absolutely love your look today. The dress and boots are amazing! Have a lovely weekend. Gemma x

    • Jodie Filogomo

      Thanks so much Gemma!!
      Happy weekend to you too!!

  • Judy Gramith

    Your outfit illustrates how you’ve enthusiastically embraced pattern mixing! I really like the pattern of the dress/jumper with those awesome booties and that little fish pin is so cute!
    I’m not sure I like Nancy’s outfit. The white of the dress and blazer seems too much of a contrast with the beige and browns of the booties for my taste.
    Charlotte’s geometric patterned jacket is really cool and illustrates the longevity of some pieces. I really like it with the boots!

    • Jodie Filogomo

      I so appreciate your comments Jude!!
      I can see how Nancy’s dress & blazer contrast to her booties. Maybe I should have grabbed her olive jacket? That might have complimented it better?
      I know why I picked this striped jacket—it was her newest one and I wanted to show it off. But sometimes it pays to search among the oldies but goodies too!!
      Happy Weekend (and I just sent you a text!!)

  • Your floral booties with your bare legs really makes them stand out! I’m now convinced this is how they were meant to be worn.

    I really am squarely in the camp that ankle booties with a dress or skirt will make me look shorter, not that I haven’t done it, but I rarely look back on those looks and feel like they were the right choice.

    • Jodie Filogomo

      I have been loving these floral booties!
      And when I bought them, I know I never thought I’d wear them with a dress….but they are quite low cut, so I’m glad I tried it!

  • You picked some great looks. I love wearing ankle boots with dresses during the colder months.

    • Jodie Filogomo

      Thanks Izabela!!
      I’ve done it with tights before, but I haven’t been as open to bare legs—I’m glad I tried it!!

  • fantastic outfits. I love ankle boots, also in the summer but then with a peeptoe!

    • Jodie Filogomo

      Thanks Nancy!!
      I do think they are so functional yet stylish!!
      Can’t wait to see your leopard ones on your feet soon!!

  • This is my favourite combination Jodie!
    Ankle boots and skirts look so modern.

    • Jodie Filogomo

      Thanks Samantha—-it is what you see on the “young kids”, huh?
      Might as well join in on the fun!!