I am assuming that you want a season appropriate answer, so at $280, the APC suede calfskins are a steal compared to the overpriced pieces being pumped out by Car Shoe and Tod’s.  The Leffot Disco Penny is also another solid option that will keep you fresh throughout the summertime.

Unfortunately, driving shoes are extremely delicate and aren’t designed for city living.  Even worse, the soles are irremovable, and I’ve never heard of a cobbler gluing in a new set of spikes.  So, looks like you’re out of luck, my dude—just rock them ‘til the wheels fall off.

Edit - I have never heard of the below procedure (and think it sounds a little dubious), but Compulsive Awesomeness comments: “To the tod’s questionI had a couple of Ralph Lauren driving loafers that were almost identical to Gommino Tods and wore the heel off as well… my cobbler replaced the sole with a very thin rubber sole and kept the back hel numbs so they look almost as new and I had them for over 4 years now”

I hit Woodbury twice a year—it may not have all the lastest fashunz, and while it’s usually hit (walk-off grandslam) or miss (strike out with runners on and two outs down by one in game seven of the world series), it’s definitely worth the trip.  In no particular order, check out these spots:

• Barney’s
• Cucinelli
• Brioni
• YSL
• Dior
• Moncler
• Zegna
• Etro
• Bally
• Tod’s
• Ferragamo
• Cavalli

And always, always, always do the right thing by picking up your lady something from La Perla and DVH.

PS - Oh, and Cinnabon FTW.