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!