Fashion Over 40: Chic Outfits With My Most Comfortable Shoes

Heather Anderson
by Heather Anderson

Let’s talk about fashion over 40. We all would love not just to look good but feel good too. I’m going to show you some of my favorite comfortable shoes for women over 40.

Veronica Beard sneakers

1. Veronica Beard sneakers

Sneakers are comfortable shoes for standing all day. If you pick out the right style of sneaker you can be comfortable and still look stylish. That’s why I love these white and gold Veronica Beard sneakers. I love that these sneakers have a bit of a platform too.

Veronica Beard sneakers

Try to stick with a neutral color pallet to stick with a classier feel. Try pairing your sneakers with some white jeans, a white tank top, and a denim jacket. This is one of my favorite comfortable chic outfits.

Black New Balance sneakers

2. Black New Balance sneakers

I love my black New Balance sneakers with the white accents. They are so comfortable and go with so many different outfits. Try wearing your sneakers with some black leggings, a black tank top, and a grey hoody.

Tony Bianco silver heels
Sarah Flint champagne strappy heels

3. Tony Bianco silver heels

Now let’s talk heels. You want to look stylish, but you want to be comfortable!


My tip for comfortable heels is to find something with an open toe and a three-inch heel that’s not too skinny. I love my silver heels because they go with anything. I wore mine with a strapless yellow dress.

4. Sarah Flint champagne strappy heels

I have one pair of heels that are the exception to my rules. These are 4 inches and they have a thin spikey heel. They’re actually the most comfortable heels I own though because they have this nice padding for the arch of the foot. I love the way these look with a crochet red dress.

Marc Fisher white kitten heels

5. Marc Fisher white kitten heels

The next comfortable heels are these white slip-on kitten heels. Kitten heels are really trending this summer. I love pairing these shoes with some jeans, a fitted tank top and my navy blue tweed jacket.

Sam Edelman flat slip-on sandals

6. Sam Edelman flat slip-on sandals

These are so comfortable because they also have a padded heel in addition to being flat. Try wearing your slides with some denim shorts and a button-down tied at the waist.

TKEES gold strap slides

7. TKEES gold strap slides

These are very luxurious and glamorous-looking flat slides. Try pairing them with a simple mini dress like my dark denim dress.

Simon Miller thong kitten heels

8. Simon Miller thong kitten heels

These thong-style kitten heels are just one and a half inches. I love them in silver. Silver shoes is another current trend I’m seeing a lot of.


I’m wearing mine with some jeans and a simple tank top, but these go with everything. You can wear them with skirts, shorts, dresses, or whatever else you want.

RAYE silver lace-up sandals

9. RAYE silver lace-up sandals

These shoes are very stylish with their silver color and their lace-up straps, but because they’re flat they’re also extremely comfortable and wearable. I love the way they look with a denim mini-skirt, tank-top and, white denim jacket.

RAYE espadrille wedges

10. RAYE espadrille wedges

These are the perfect vacation and summer shoes. They give you some height from the platform, but they’re still extremely comfortable because the pitch is not that high. These look great with denim shorts, a white strapless shirt, and a straw beach hat.


Fashion over 40

I hope you enjoyed seeing some of my favorite casual comfortable outfits and shoes. Remember, you don’t have to sacrifice style or comfort to be fashionable over 40.


Which looks were your favorite? Leave me a comment to let me know.


Next, learn How to Look Expensive on a Budget.

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 1 comment
  • Mia Mia on Jul 09, 2024
    I thought the white sneakers were cute, but $295 is insane. 🤯
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