Ah ha! Timberlands. More than likely cemented ie plastic sole unit just stuck to the upper. They will always 'gap' where they flex and will never be waterproof as they were never designed to be. Best thing to do is plaster them with Dubbin and let it soak in. The only constructed leather footwear that is waterproof is 'veldtschoen' which are expensive. If you want waterproof and cheap buy a pair if wellies. If you stll have problems PM me.