As much as I enjoy browsing at Topman on Michigan Avenue, there is rarely anything there for me. Loathe as I am to admit it, I no longer have the heroin-chic, skin-and-bones physique to rock their super-skinny bright-blue pants. Not to mention, I’m a little too, ahem, old for that look. But one thing I consistently find there that keeps me coming back: shoes. Brogues, loafers, plimsolls, sneakers—they have them all, and often for a song. I have built quite a collection of $50 to $80 Topman shoes because I’ve been willing to wait and willing to pop in on a regular basis for a price status check. Every pair has looked great and worn remarkably well. Currently, I have my eye on the Peter 2 Boots. They aren’t on sale yet. But when they are, I’ll be ready to pounce.

$170 at Topman, 830 N. Michigan Ave.  312-280-6834; or