Very comfortable right out of the box! They're excellent quality and seem like they'll be durable. I have plantar fasciitis, so I have to wear orthotics, and they fit well in these shoes. The liner comes out, so my orthotics slide right underneath. Also the liners really wick perspiration. These are toning shoes and it says right on the box that they are not to be worn during exercise other than walking. They feel very stable and supportive, so they're not like those rocking toning shoes that I'd probably sprain my ankle with in 5 minutes. They're cushy, almost bouncey - exceptionally comfortable. In fact, I love these shoes so much, I ordered a pair of the same ones in brown. I wear them to work with my dress slacks and no one even notices. I guess if you're one of those people who's fussy about having the latest fashion statement on your feet, you wouldn't wear these to the office, but at 5 p.m. my feet still feel great and I don't hobble to the car like everyone in their stilettos. I also wear these with shorts and they look stylish and appropriate. Great shoe!