How to Wear Ankle Boots with a Skirt: Fashionista Approved

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Ankle Boots for Women over 50

How to Wear Ankle Boots with a Skirt: Fashionista Approved

How to wear ankle boots with a skirt couldn’t be easier. Put on a skirt or dress and then add your ankle boots to your feet. I’m sure you’ve heard the rule about not breaking 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!

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

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!

Besides, I think the idea of trying to appear taller or any kind of “er” is long outdated. Who decided that taller is better anyways?

Tips for How to Wear Ankle Boots with a Skirt

If it seems strange to combine something dressy like a skirt with ankle boots, then here are a couple of tips.

  • Try an ankle boot with a lower profile. There are ones that are very short on the leg line, and feel more like a loafer.
  • Stick with a color of ankle boots that matches your skin tone. Then they will look more like your leg.
  • If you have darker ankle boots, then wear the same color of tights as the booties. This will make them seem more like taller boots.
  • Many ankle boots have asymmetrical topline which can be more interesting.
  • If you feel you need a dressier ankle boot, they are many with heels and dressy elements.

Most of all, have fun with this idea of how to wear ankle boots with a skirt. You’ll never know until you try it.

Buying Ankle Boots Online

Shoes are hard to purchase online because the comfort factor is impossible to consider until you try them on. Yet, in this day and age, the convenience makes the online purse idea wonderful.

Here are some tips for successful online shoe buying

  • Before anything, check the return policy of the online store. This should give you either a red or green light if you should even stay on the site. Most of the time, I look for the option of free returns or being able to return to the store. Unless you already are familair with the brand.
  • Read the reviews. If everyone says to size up, then take their advice.
  • On the other hand, it can be more successful to purchase two different sizes. Since you already know the return policy, it shouldn’t be a surprise on how to take back the other pair.
  • Don’t count on the color being exactly the same. The colors on our computer monitors can vary greatly.
  • If it’s a brand you aren’t familiar with, check to see if it’s carried at a store near you. Then go to the store and try on the some of shoes first.

Eve of The World According to Eve

In Eve’s words “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

Sheela says: “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

How to Wear Ankle Boots with a Shift Dress

Jodie’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 braver 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, which is almost hiding!! It’s more like a surprise when you look closely!

Insider tip: Tying a scarf doesn’t have to involve a lot of flips and twists. You can always use any brooch to hold it together.

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)

How to Wear Leopard Ankle Boots

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!
This is such an easy way to print mix. Adding leopard ankle boots to a striped jacket. It works since they are farther apart and both are composed of neutrals.

Fashion for women ages 50 and older.

I thought the brown earrings would pull in the brown from the ankle boots.
Nancy always likes the smaller earrings, so they aren’t large enough to notice from far away. But it’s still a nice detail to add in more brown items like is in the booties.

Fashion for women ages 50 and older.

Other outfits with this same white dress

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 & How to Wear Ankle Boots :

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 of 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 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

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Welcome to Jodie’s Touch of Style. I’m here to prove that it’s never too late to look great. Clothing and style are meant to showcase your inner personality. So let’s have fun and try new things.

It’s not just about me on this blog, but also my mother and friend. We get to showcase not only different decades of life but also different body shapes and unique personal styles.

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