I have Madden's size 6.5, do these size the same way?

They run true to size. I am a 7.5-8 and I got an 8 and they are perfect!

What kind of socks do you wear? If any?

Normally no socks but sometimes the thin half-socks.

What is the difference between regular and medium

Not sure... I wear a size 7 and purchase 7 regular and they fit great

Do these run big/small? I am typically a 5.5 but was wondering if I could get away with a 6?

They run small. I would get at least a 6, might want 6.5 depending on how much room you have left on your bigger foot in your regular size.

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Womens Bayshore Plus Ii

Product ID: 456528911

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Description

Women's textile shoes with embroidered or printed heel detail and Roxy flag label, including cotton laces, rounded off with a cushioned insole with memory foam and graphic print.

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