Win it: The Allen Edmonds MacKenzie Wholecut Oxford

MacKenzie Medallion Toe Wholecut – $237.60 – $425

NOTE: The brown options are on sale for $297, and you might be able to use the code PLUS20 for an extra 20% off that sale price. No word on when that code expires though. The walnut shade is currently sitting at full price, which is $425.

Wholecut shoes somehow manage to be both totally modern yet oddly classic, all at the same time. By their nature they’re sleek, minimalist shoes, yet they’re also the essence of what a shoe is. They are by definition, the type of shoe that uses the least amount of materials to create the upper. Just one piece of leather. And that means there’s nowhere to hide any attempts to cut costs.

Some think wholecuts can look a little too minimalist. And that’s why adding a medallion to the toe, just like what’s featured on the Allen Edmonds MacKenzie, ends up creating (for some of us) the perfect dress shoe.

Recently introduced to the Allen Edmonds lineup, the MacKenzie is built on their 2531 last. Which… I honestly have no idea what that’s comparable to. But as someone who loves his Strands, a 10.5 D in the MacKenzie fit my foot surprisingly well. With such a “fancy” shoe, I was expecting maybe some fit concerns. But that wasn’t the case at all. If you’re a fan of the 65 last (the one that Strands and the Park Ave. are built on) you should do well with the MacKenzies in your normal size.

The toe is round. No chisel action here. And they’re sleek but not spear like. Again, they somehow balance timeless looks with a modern minimalism. And the walnut leather shown here really is something. Reminds me of my Liverpools. Flexible, smooth, and comfortable right out of the box.

Still Goodyear welted. Still made in Wisconsin. Still recraftable. They’re a sexy shoe, but they’re also proof that sexy can be practical as well as a solid, long term investment.