Secrets of How to Look Stylish in Comfortable Shoes

Secrets of How to Look Stylish in Comfortable Shoes

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3 decades of style

Secrets of How to Look Stylish in Comfortable Shoes

Overall, how to look stylish is easy when all of your pieces are fabulous. Often I say that shoes can make or break an outfit. And I had a reader voice a concern that she feels her shoes often fall into the “break” category.

Quote of the day: “Every readers catch-22: The more you read, the more you realize you haven’t read; the more you yearn to read more, the more you understand that you have, in fact, read nothing.” Pamela Paul

What does the quote above have to do with how to look stylish in comfortable shoes? It spoke to me because while I have a blast styling fashionable shoes, I haven’t had much practice with the more utilitarian styles.
In fact, this idea all started because Walking Cradles asked if we would be up for the challenge of styling some of their other footwear. We were gifted these shoes but I was not paid to write this post.

So the three of us put our heads together (along with our feet LOL) to share our secrets of how to look stylish in any kind of footwear.

First let me introduce the shoes, why we each picked these, and our review of them. Then I’ll share the secrets we employed of how to look stylish.

How to look stylish in flare jeans

Walking Cradles Eliot

The Eliot from Walking Cradles is touted as a loafer, but I would call it a low ankle bootie. It comes in this color called Lugguge, and also brown and black.
I’m showing how it’s adjustable with velcro across the instep in the photo below.

1-I found these to be so comfortable just like all of Walking Cradles’ shoes with the tiny pillows in the soles.
2-There is a “real” heel and it’s only 1 inch.
3-These have a rounded toe and tend to be clunky. To my husband, they remind him of the hippy shoes from when he was growing up.
4-The leather is very soft.

Fall outfit for older women

A New Boyfriend Called Emerson

Lesley foresees a long loving relationship with this shoe called the Emerson from Walking Cradles. She chose the warm taupe color, and they also come in brown, black and navy. These are described as a clog style on the Walking Cradles’ site, but you could also call it a mule.
Knowing they are a clog style reminds me of a blog post that I published years ago. It was when I had a request to style these types of shoes but didn’t have any in my closet. SO I asked a friend to help me out.

1-Lesley really appreciates the easy in and easy out ability with these kinds of mules/clogs. It makes it easy to slide on to take the dogs on a walk.
2-There is an inch heel that Lesley said was VERY easy to walk in and better for her back and posture than just a flat flat.
3-If you have any heel pressure points, these are shoes for you.

How to look stylish with footwear

How to Look Stylish in the Camden Style

The Walking Cradles bootie called the Camden is another I would describe as a short ankle boot or loafer. Charlotte is wearing it in brown, and it comes in black also.

1- Again, the consensus is these shoes are truly comfortable because all of Walking Cradles have the tiny pillows in their soles
2-They have a zipper on the top side. My mom chose this style because of that zipper. She has a bump on the top of one of her feet, and wanted something that she could adjust if it pushed on the bump.
3- There is a 1 inch heel but this one is more of a wedge heel.
4-The leather alternates with the lizard print to give some visual appeal.

Secrets of How to Look Stylish

Even if you have an item in your closet that you know is not incredibly stylish, you can work around that. There are secrets that we’ve employed and I will share to still look stylish.

Other blog posts about the idea of frumpy
What Exactly is Frumpy?
How Not to Look Frumpy: Viewpoints and Simple Examples By Millennials and Midlifers

1-Put the emphasis on other parts of the outfit. Since we were concentrating on the shoes, notice that all of us wore a hat. It brings attention to our face.
This is the magic of accessories including scarves and big earrings too.
2-Include a showstopper item. You know, a clothing piece that has a lot of color or interest. For me it’s my jacket. Charlotte wore a pop of color with her purse. And Lesley’s colorful scarf is front and center.
3-Sometimes the best idea is to put more attention on the item that you don’t believe to be stylish. It’s like the elephant in the room, and maybe you can accessorize or make it fun. With shoes like Lesley’s, you could add in a decorative sock to make it more whimsical instead of serious.

4-Another idea with shoes is to match them to the pants/skirt so they blend in. My mom showed how to do this with a matching skirt and hose recently even though her shoes were stylish. And she’s doing it again with the brown pants and shoes.
5-Think about what the style of the “unstylish” piece is. For example, Rob thought my shoes looked hippish. So I dressed in a boho like style with the flare jeans and this blazer. Then the shoes fit into the overall look.

Women over 50

More About Walking Cradles

I am an ambassador for Walking Cradles which means I am here to tell and show you more about this company that I love. What this means to you is if you ever purchase anything from their site, using my link, I receive a small commission.
FYI, I can’t link with my affiliate link to the specific shoe, so once you go to Walking Cradles site, then search for the style. Or feel free to browse all of their styles.

Walking Cradles is a small business that I discovered over 2 years ago. Since then, I have added many of their shoes to my closet both gifted and purchased with my own money. Why? Besides the fact that they have sizes from 4-13 in narrow to wide wide, they also care about their customers. They use “real” women as their models and their shoe designer is a woman. That means they try to make their shoes work for every age and foot.

I have a code, JODIE15, that can be used on your first order on the Walking Cradles site. Once you start loving them a much as I do, of course you should sign up for their loyalty points and newsletter. Please, consider always going through my link before ordering any footwear from them, so they know that this type of marketing is working.

The only disadvantage is to my overseas friends, as Walking Cradles only ship within the USA right now.

How to look stylish in comfortable shoes

Photo credit: Rob Filogomo

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