i am SUPER picky when it comes to shoes. I am pretty stylish and I have had a really hard time finding stylish comfy shoes to take to Thailand. these fit the bill. The are GREAT quality and they fit true to size. I wear a 9 and it was great, even room for a sock if I dared, which I wont. The cords/straps across the top were fine, they did not dig into my foot nor were they super loose. I think my instep is average. They look great with my PrAna capris and Horny Toad shorts, I don't know about a skirt, I wouldnt think so. Even jeans they are fine. Again, these aren't shoes I would wear all the time bc of the style, they are perfect though for recreational use and traveling when you are walking on varying terrain and its hot!