I bought my first pair of Bostonian shoes 4 years ago and that has been the greatest investment in shoes I have ever made. I still have those shoes and they are still the most comfortable shoes I have ever worn. I can say that they are even more comfortable than tennis shoes! The kind that I had bought were the Bostonian Blues. They have a special insole that cushions your feel all day long. I cant remember the name of the insole, but it was specially made for their shoes. Im sure you can find something similiar in other shoes, but these were the first dress shoes that I could wear ALL DAY, and my feet would not complain. They cost me $115, but it was well worth it because they have lasted me 4 years. Since then I have purchased 2 other pair of dress shoes and I still go back to my Bostonians for the comfort and style that I like. I just recently bought a new pair of Bostonians. They didnt feel as good as the Bostonian Blues, but after I broke them in, they feel awesome! I didnt even have to break in the Bostonian Blues, they were a perfect fit. If you want to get your moneys worth, then purchanse a pair of Bostonians. Dont be cheap and buy crappy dress shoes, especially if you have to be on your feet all day. Save your money and really consider investing in your feet, because that is where all the back problems can be traced. Dont delay, save if you have to and invest in Bostonian shoes. Im so glad I did. -A side note: I was a college student when I bought these, so I wasnt rich at the time.