With so many booties out there to choose from, it took me forever to decide on a pair but unlike the other reviewer, I was pleasantly surprised.  I have only worn them with little anklet socks, but have never had a problem as far as comfort or them digging into the backs of my heels.  I wear these with everything and will probably end up getting them in black too!  I also purchased the Dolce VIta Halle boots in black and after wearing them once, I was so much happier with this Sam Edelman pair.  The Dolce Vita's were tight and not as comfortable as these boots.