Most Comfortable Mary Jane Shoes for Women Over 50

Mary Janes have come a long way from the shoes we wore as kids. These days, they’re a popular shoe choice, which makes them a great option for women who want shoes that are both stylish and comfy. They’re a great alternative to sneakers and work well with everything from jeans to dresses. Let’s take a look at some Mary Jane options that keep your feet happy all day long!

SQUARE TOE MARY JANES / BARELY BOOT JEANS size 8P / FLEECE POPOVER TOP size S / EARRINGS
/ ZIPPERED TOTE BAG

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How to Wear Mary Janes for Women Over 50

I got a new pair of the same style of Mary Jane shoes for school each September for more years of my youth than I care to remember. My wide feet made anything else impractical. One year, they were red, the next black, then they were navy, followed by brown…you get the idea. It was painfully boring, so once I grew into my wide feet, I went in search of interesting shoes and never looked back.

When Mary Janes re-emerged as a popular shoe trend last year, I decided to give them a try. I hadn’t worn a pair since I was a child and worried they would look silly on me. I found them to be surprisingly comfortable, fun, and quite versatile.

I’ve found that the best way to wear these shoes at this stage of life is to keep the rest of your outfit’s details simple. I’d steer clear of overly “sweet” outfits, like floral dresses or ruffled skirts, as they can feel a little too precious.

Most Comfortable Mary Janes for Older Feet

COMFORTABLE MARY JANES FOR WOMEN OVER 50
SAM EDELMAN MICHAELA MARY JANE FLAT

These were my first pair of Mary Janes as an adult, and they did not disappoint. The cushioned insole makes them comfortable enough to wear all day. They come in a wide variety of colors and materials, from tweed to metallic to velvet. Most styles are available in sizes 5-12, with a few select colors offering sizes from 4-14.

VIONIC ALAMEDA MARY JANE

It wouldn’t be a comfy shoe list without mentioning at least one pair from Vionic. These Vionic Mary Janes are made with their signature arch support, so they’re great for long days on your feet. They come in narrow, medium, and wide sizes so that you can get the right fit, and the velcro strap makes them super easy to slip on and off.

COLE HAAN BRIDGE MARY JANE FLAT

I love the subtle croc texture and shine of these Cole Haan Mary Jane flats. They’re also available in black patent and a pretty textured gold in sizes 5-11.

ROTHY’S THE MAX SQUARE MARY JANE SHOE

I’ve been a Rothy’s fan for years. Their shoes are machine-washable (my favorite feature), but they’re also super durable because they’re made from recycled plastic. Their website says, “So comfortable, you’ll think you’re just wearing socks,” and I couldn’t agree more.

When I started looking at their Mary Jane styles, I couldn’t decide between two options. I ended up going with “The Square” in black, which has a slightly rounded toe, but I also really love the more squared-off style of “The Max.” Both are available in sizes 5-13.

REGENT BLAZER size 10P / TURTLENECK SIZE MP / CUFFED JEANS size 29 / MARY JANE FLATS / HANDBAG / SIMILAR CHARM NECKLACE / BELT
DANSKO FAWNA MARY JANE

Dansko shoes are known for being incredibly comfy, and this Fawna Mary Jane gets excellent feedback! Reviews mention they’re comfortable right out of the box, thanks to a sturdy sole and a removable molded EVA footbed that provides plenty of arch support. Perfect for all-day wear, these shoes are available in sizes 5-13 in medium and wide widths.

NATURALIZER KELLY MARY JANE

Last but not least, I wanted to share these from Naturalizer. They have a great classic shape that can be dressed up easily with a trouser, skirt, or dress. They’re available in 5-12 Medium and 6-11 Wide.

MORE MARY JANES

I’m noticing the trend in Mary Janes this year is for a longer toe box that extends over the top of the foot more. They look less like a ballet flat with a strap and have a more substantial feel on the foot. That means they also bypass my bunion, which is a plus for my older feet.

How do you feel about Mary Janes? Will you be giving them a try this year?

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34 Comments

  1. I adore Mary Jane shoes! They offer me a French Girl look. When I realized I could no longer wear high heels, I started looking for lower heel options. Loafers, ballet flats, and sneakers serve as flat options. Mary Jane’s with lower block heels were the solution for dressy shoes for work. I first discovered the Tartt pump from Sarah Jessica Parker – I have them in pink patent, white patent, and gray snakeskin. Last year, I found the Madewell Nettie and have them in black leather, silver leather, and brown suede. I splurged on a pair of Christian Dior Mary Jane pumps that go with everything. These all work with dresses, skirts, pants, and jeans. I have noticed lot of dressy pumps that are a modified Mary Jane style like the LifeStride Madelyn. I am happy with the style and the comfort!

  2. Brenda English says:

    Jennifer- I love your style, we are very similar in size and shape. I remember seeing leather and cork slide sandals on one of your posts and I can’t find them. Could you please remind me who makes them. I think they were an Italian brand?

    Thanks,
    Brenda

    1. What color were they

  3. Christine Arquilla says:

    I grew up wearing corrective shoes (either saddle shoes or brown or black “grandma” oxfords) until I was 11. The only Mary Jane’s I remember wearing back then were white ones for my First Communion. Luckily, I grew out of the foot problems and have been able to indulge in wearing whatever shoe I want up until the last few years. I like how Mary Janes look on me. I just need to made sure the toe box isn’t too round and the strap isn’t too wide. Proportion can make all the difference between looking fashionable and precious. I think I’m going to give a pair of the Vivaia shoes a try. I love the kelly green color they show in their ad. They would match some of my favorite office blouses and jackets.

  4. Hi Jennifer, you look good in everything you wear. I have to pass on the Mary Jane trend. They feel too cutesy on me. I am a huge Rothy’s fan but I stick to the regular flats and the points.