Full disclosure: I just got these boots today, but they are the absolute most comfortable boots out of the box I've ever worn. By a long shot. Time will tell if they hold up (and if they don't, I'll be back to edit this review) but for now, they are great.
AMAPO Men'S Mid-Top Dress Boots: A Perfect Blend Of Style And Comfort With Side Zipper And Lace-Up Closure
37 Review
AKARMY Men's Outdoor Military Tactical Pants: Rip-Stop Camouflage Cargo Work Pants with Multiple Pockets
45 Review
Men'S Waterproof Backpacking Boots For The Outdoors
36 Review
Waterproof Cold Weather Boot For Men By Kingshow (Model Number 1586)
46 Review