Very likely yes! It partly depends on why the shoes were put on, and why you want them off. If he was shod because of a mechanical problem such as occurs with past founder, or a structural problem with the foot it might not be advisable to leave him barefoot. If he is tearing shoes off you might not have a choice.
If possible, plan ahead. A month of Equinell™ Hoof and Mane Oil will make the transition easier, by drying out the feet, and making them more comfortable. Try not to over trim when the shoes come off; the feet will tend to bruise, and you want as much horn as you can, for protection. If the shoe is already off, keep him on soft ground for a while, and use Equinell™ Hoof and Mane Oil weekly until he is comfortable and his feet look good.
Be very aware of bruises. These tend to form sterile abscesses, and Equinell™ Hoof and Mane Oil cannot help prevent them, except by generally improving the overall condition of the hoof. However, if they do occur, and are drained, Equinell™ Hoof and Mane Oil can help them return to normal faster.