From casual to hot date, comfortable shoes you can walk in all day long

Let’s talk about the most comfortable shoes I own…

I like to walk. According to my FitBit, I walk about 11k steps a day. Which means I always like to wear comfortable shoes… even when I’m dressed up. This is my roundup of my comfortable shoes, from casual to hot dinner date, that you can walk in all day long…


If I had to pick ONE thing to wear on my feet for the rest of eternity, it would be a pair of single layer Men’s Rainbow sandals. (Although my Rainbow tan on my feet would probably argue that I’ve already made that choice years ago.) I have these in grey, tan, and a really pretty dark pink that they don’t make anymore.

Click here to read everything you need to know about these amazing boots. The tl;dr of it: I live in these. You should too (but not to the same event though, okay?).

Much like my Rainbow sandals, Chuck Taylors have been a shoe staple for me since the ’90s. I can’t even remember how many pairs I’ve burned through, but right I have a pair of these in black and purple.


Vagabond Grace Lace-Up Boot

Vagabond Grace Lace-Up Boot from Urban Outfitters

You might recognize these boots from this post. Would you believe I walk miles and miles in these babies all the time? This is my go-to shoe for a dinner date followed by a long late night stroll. Sexy and comfy.

Black Milk’s I Eat Mice shoes from Solestruck.

These were a birthday present to myself. I debated getting the kitty cat print ones, but I figured this cool snake skin pattern can be both dressed up and down. I also spent three hours in these while alternately standing in line in a courthouse and walking back and forth and up and down in said courthouse. I’m thinking of getting ALL styles of these bad girls.

You guys should stop reading this and buy these sandals right now, because they’re on sale for $5 and they’re STUPID AWESOME!

Your turn!

Please help me, and help everyone reading this, by leaving YOUR suggestions for the most comfortable shoes EVAR in the comments.


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  1. Justin cowboy boots. Strangers always compliment me when I wear them and they are legit comfy.

    • meganfinley

      WHAT!? Why have never seen you in cowboy boots. I can’t wait to see these in action.


    FLUEVOGS. (I have this pair in cherry red, and OMG. People fall to their knees).

  3. These Me Too flats are my faves:

    They require no breaking in and don’t blister my feet at all. They don’t last more than a season before they start to fall apart, but that’s okay by me for the trade-off of just being able to throw these on and GO.

  4. I live in my Keen Clearwaters every summer, my Minnetonka moccasins during the shoulder seasons, and my Merrell Captiva boots when the weather requires it.

  5. Sarah Brewer

    Sanuks! These are the style I have but there are so many other options and all are so damn comfortable!

    They’re like Toms that last more than 6 months 😉

  6. Beretta

    My Frye boots.

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