Timberland offers its Timberland Men's Mt. Crescent Waterproof Jacket in four colors (Black pictured) for $31.49 with free shipping, via the directions below. That's $89 below list and the lowest total price we could find. It's available in size S to XXL. To get this price:
Timberland offers its Timberland Men's Earthkeepers Heritage Boat Shoes in seven colors (Brown Smooth pictured) for $79.99. Add them to cart and apply coupon code "welcome15" to drop it to $50.39. With free shipping, that's the lowest total price we could find by $32. They're available in sizes 7.5 to 13.