eBay has the Under Armour Men's UA Stellar 8" Tactical Boots (Black) for $56 with free shipping. Available in select sizes from 8W to 12.5M.

Nike is offering Nike Men's React Element 55 Shoes (Black/Light Thistle/Pollen Rise/Magic Flamingo) for $55. Shipping is free for Nike+ members (free to join).

Amazon has the Marc Joseph New York Men's Leather Chukka Ankle Boots (several colors) for $26 with free shipping. Has excellent Amazon Reviews.

eBay has the ASICS Tiger GEL-Kayano 5 OG Men’s Shoes (white/black) for $33 with free shipping. Features fabric-and-synthetic, rubber sole, the shoe features classic 90's aesthetic, bulky silhouette, heavy use of overlays.

Amazon has the Cole Haan Men's Williams Wingtip Oxford (British Tan) for $59 with free shipping. Has good Amazon Reviews.