When I got these boots, it was only my 2nd pair of docs.  I didn't realize how sturdy the leather would be, so I did not wear the "right" kind of socks the 1st few time I wore these boots.  Word to the wise- until these boots are broken in, be sure to wear thick enough socks or band aids on your heels..... Now that I have fully broken in my boots, they are much more comfortable.  I wear them with jeans, cords, or shorts.  They are very sturdy & supportive.  Great Boots!!!