Comfortable nautical shoes

I don't do uncomfortable shoes. Seriously. I rarely wear heels (mostly because I am tall and I just can't get used to them) and if I get blisters I don't wear the shoes again unless I really really love the shoes. Last winter I fell and broke my foot. I was wearing flip flops, holding H, and didn't see a huge hole in the dirt at a park. I probably would have been fine but the flip flops gave no support. Thankfully H was fine. Phew! But I had to wear a boot for months and I still have pain if I walk in sandals for a long time. SO I really try not to wear sandals/flip flops to work anymore. It's just not practical (we take a lot of walks!) or safe.

I have had to get creative on shoes that are practical for running around with a toddler but also not hideous.

TOMS Nautical Oxford are so adorable. No blisters and comfortable for long walks


The Webster at Target nautical ballet flats (these are sold out in most sizes. But there's a solid pink version too). I've NEVER received more compliments on anything I own! When I wear these shoes I get a minimum of three strangers saying they are so cute and asking where they are from. It's crazy! They are comfortable too! I've yet to get any blisters in them.


I am not embarrassed to admit I ordered these Crocs. They were way too big and had a complicated return policy (you return and then place a new order-I just wanted to exchange when I returned!). I am going to order another size. They were so comfortable.

Have you found any comfortable (cute) nautical shoes recently? Please share your finds!