I buy a new pair of these shoes every year for $85 and you can't beat the quality/comfort ratio. They may not be the best dress shoes out there, but spending $90 a year on shoes that I wear every day with all-day comfort is no problem.
Men's Merrell Jungle Waterproof Slip-On Loafers in Gunsmoke - Shoes for Superior Comfort and Style
47 Review
Ultimate Comfort and Style: Minnetonka Men's Sole Moccasin Taupe
46 Review
DANSKO Wayne Black Size 11.5-12 Regular
51 Review
Wool Blend Slippers Heathered Leather Maximum Men's Shoes and Loafers & Slip-Ons
58 Review