Hanes via eBay offers the Champion Men's Authentic Cotton 9" Shorts with Pockets in four colors (Black pictured) for $8.99 with free shipping. (Amazon has them for the same price with free shipping for Prime members.) Excluding the mention below, that's the lowest total price we could find by $3. They're available in sizes S to XXL.
A close price: Sears has them for $9.49 with free in-store pickup.
Sears offers the Fila Men's T-Minus Running Shoes in Black/White for $19.99. Coupon code "ADORE" drops it to $16.99. Opt for in-store pickup to avoid the $5.49 shipping charge. That's the lowest price we could find by $19. They're available in sizes 7 to 13.
Sears offers the Covington Men's Ogden Dress Oxford Shoes for $34.99. Pad your order over $35 to bag free shipping. That's the lowest total price we could find by $37. They're available in medium and wide sizes from 7 to 13, although not in all size/width combinations.