Any park apparel/shoe advice for "Pooh sized"?

As far as chaffing...get body glide. I bought it at dicks sporting goods. It looks like deodorant. My son gets chaffed on his belly and inner legs from the beach so I coat him so he doesn't get sand burn. Bc tulle he coats himself now.

Body Glide ROCKS
 
I love my Sanuk yoga mat flip flops. They're around $35. So comfy! The first time I bought a pair I bought the "spree" kind because I liked the thinner band. It was a mistake, the footbed wasn't as comfortable as the original kind.

I almost always wear dresses with spanx under them. I wear spanx every day of my life though so I'm used to them, I know some people can't stand them. They do make some that aren't crazy tight compression though, I think they're the power panties. They prevent the chafing and then I can wear a dress and not be overly hot. But compression bike/athletic shorts would accomplish the same thing. The only issue I've had with them since I started working out is that the waist band is usually tight enough to give me muffin top even though the pants are loose everywhere else. Might not be super flattering. That's why I love spanx, they smooth everything.

Usually one day on our trip I'll wear a pair of Bermudas. I'm 5'8 (right around the same weight as you) with long legs and old navy's hit me maybe 4" above my knee and I have no chaffing issues. It took a lot of Disney trips for me to figure out my no-chaffing strategy while still being comfortable and looking nice and put together. It's tough, I feel your pain :).
 
Similar as your size,
For walking I take three shoes to swap out. I have Sketchers with memory foam, I need my feet to breath at some point during the day so I switch to my NIKE sandals that have memory foam.
Then the reliable Crocks, Mary Janes with either foot powder or those little socks you try shoes on with.

Especially with rain, I let the. Crocs dry, and put a pair of nude slip socks on, it's warm and comfortable.

I like to take my Disney T-shirts, and some tanks in flowy material from Sears or Kohls, and Thin material Capris or Bermuda shorts. Mine have a thin tie just below the knee I leave loose and are soo light.
I do have two sun dresses and were either thin biking shorts, or panties with short legs to keep from rubbing no matter what size I am.

I keep gold bond or other good powder and the body glide! but if wearing a dress body glide wears off without legs in the pants/shorts underneath. I found one day I was sooo warm and uncomfortable I went back to the hotel, went in for a short dip to cool off, then back to the park for MNSSHP for 4:00pm. That dip refreshed me and allowed me to make it a late night.
 






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