It takes a courage for a man to wear UGG boots, but it can be done. If you have the boots, but are for whatever reason ashamed of having them, cover up the ankle part of them with you pants. If you wish to flaunt your several hundred dollar boots, let the front part of your pant bottoms be loose over your boots, but prop the back part of your pant bottoms on the tops of your boots. Remember, never ever tuck your pants into the boots. If you follow these simple strategies, it is possible for a man to wear Uggs and look good doing so.