Five must have fall shoes for comfort

Every morning I sit across from my cousin and write. There are times we are both working on passion projects and there are times that he is just…working. Because he gets paid. His areas of expertise are varied and writes for soccer magazine, some famous gaming site, and is editor in chief for StyleForum a men’s fashion website. Yesterday he had me read his fall sneaker round up.  It made me realize for the 20,000th time how little I know or care about fashion. Some of my readers are with me. We don’t care that non-tennis sneakers shall be paired with skinny trousers. What we do care about is that our shoes are comfortable.

What then does a person who has not “fully embraced urban tech ware” wear? Here are my picks. These five shoes. Well, ten shoes, are on my feet 98% of the time. The rest of the time I am barefoot. I have included my affiliate links so if you like them I too can get paid.

  1. Dansko Flip Flops.
The orange fades to a neutral making them perfect for dress up.
The orange fades to a neutral making them perfect for dress up.

These flip flops are relatively new to my repertoire replacing the fit flops of old. (They never really firmed my ass as promised.) Like every other flip flop in the world they allow me to slip them on without the pain of sitting down or bending over. With their slightly taller than flat-foam-that we-wore-in-2nd-grade sole they make me feel less like a weeble. Plus they come in fun fashion colors. I went with orange…that faded to band aid color. Buy them for $40ish dollars here.


2. Groundhog grandpa shoe.

Imagine them pink. And yet more like a grandpa might wear them.
Imagine them pink. And yet more like a grandpa might wear them.

I have had these shoes for so long that evidently they no longer exist outside of the floor of my mudroom. You are going to have to imagine these in pink, making them my most stylish shoe by miles. Miles and miles. Which is how far I can walk in them and somehow not look as though I have totally given up. Their secret surprise? That those laces are actual elastic so once again I slip them on…but APPEAR that I can bend over and reach my feet. Magic.  Buy them for $99 here. Which might sound pricey for a shoe that is a cross between bowling and Birkenstocks but mine are 14 years and counting.

3. Frye Boots.

Mine don't even have that fancy detail at the top.
Mine don’t even have that fancy detail at the top. They are just cut straight across.

I deviate a bit with this selection because these (I think) might be legitimately stylish. Or they were when I bought them ten years ago. I went with a “fresh for fall” golden tan which matched my Carharts. I mean the color matched..not the style at all but whatever. They clunk around making me feel loud and proud. They add inches to my height, and with a bit of wiggling CAN be slipped on from a standing position. Particularly if there is a wall nearby to offer support. These used to be my go to fall shoe until I realized that the stacked leather sole wasn’t as comfortable as, say, cork or whatever magic is in the Dansko clogs. Now I pull them on when I want to be “fall fancy”. Buy them for hundreds and hundreds of dollars here. Once again I encourage you to remember that these boots will be in your rotation forever. So really its like a dollar a day for the first year and FREE forever more.


4. Converse All Stars. Slip on. Duh.

It looks like you lace them. But you DON"T.
It looks like you lace them. But you DON”T.

So there was a time when these were used for basketball. That’s why I consider them a great athletic shoe. Their lack of arch support is more than made up for by their slip on quality. When I had Leo my shoe size went from a 7.5 to a 9.5. That’s right. Two sized. I wasn’t even in denial about my original shoe size. I know because my friend makes custom shoes and he does excellent measurement. His shoe would be on this list but they don’t fit me anymore. So during the 10th month of my pregnancy I went out and bought white converse all stars with pink stars. Which should have been cute. But somehow made my feet look like the balloons they were. A few years later I admitted that they were loathesome and went shopping for a better solution. I found these and they solved all problems. No tying. Grey goes with everything, and the “laces” that stop mid foot makes me look less like a kids birthday party clown.

5. Dansko Clogs.

These. You need these.
These. You need these.

Last and certainly not least are the Dansko clogs. Any of you who have worked in the medical field or in food service can sing their praises. Plus you can dress them up or dress them down. Mostly down. By now you will not be surprised to hear that slipping them on is a big plus…as is the height that the stacked heel provides. After 15 years of 250 days a year wear I have replaced them 5 times. Always because my puppy chewed out the heel (and each time because of the left shoe.) Mine faded to a sad sickly green grey in the Denver sun and the miles of wear but a quick trip to the shoe shine brought them back to life. I recommend basic black because it will go well with all of your evening wear. These are the most important ones. Buy them for $119 here.


I'm so unstylish that I didn't know they were in style.
I’m so unstylish that I didn’t know they were in style.

When I told Jasper about my round up he asked if I would include Birkenstocks. I think there might be room for one more shoe in my life. (Or two.) Here is the fashion editors pick for best Birk. The cork foot bed compliments natural dyes. And for those of us who seek comfort…there is great arch support. Need I mention that you can slip them on?

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Anna Palmer

Anna Rosenblum Palmer is a freelance writer based in Denver, CO. She writes about sex, parenting, cat pee, bi-polar disorder and the NFL; all things inextricably intertwined with her mental health. In her free time she teaches her boys creative swear words, seeks the last missing puzzle piece and thinks deeply about how she is not exercising. Her writing can be found on Babble,, Great Moments in Parenting, Ravishly, Good Men Project, Sammiches and Psych Meds, Playpen, Crazy Good Parent, and YourTango. She also does a fair amount of navel gazing on her own blog at

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