I’ll admit it – the idea of buying clothes from charity shops wasn’t exactly natural territory for me. After twenty-five years of wearing proper suits to the office, building a…
Last week I was standing outside my office building in Chicago watching this group of tourists getting absolutely destroyed by one of those sudden spring storms we get here. You…
I'm standing in the fourth changing room of the day at an M&S in Plano, trying on what feels like the hundredth pair of jeans this month. My legs are…
Last spring I watched my neighbor Mike suffer through his brother's wedding in what looked like a really nice suit that apparently hated him back. Every time he tried to…
I need to tell you about the day I learned to never trust Portland weather, even when you think you’ve got it figured out. Was meeting this potential client at…
It started with me standing in my tiny SF apartment at 2 AM, staring at another Amazon package I’d apparently ordered but couldn’t remember. Was it the gray henley? Another…
I walked into that startup office last month wearing what I thought was a perfectly reasonable gray suit – lightweight, unlined, basically the most casual tailored clothing I own –…
So I’m grabbing coffee last week at this spot downtown, and there’s this guy in front of me in line. Nothing crazy about him at first glance, you know? Just…
About three years ago, I made what my mom would've called "a questionable life choice." I showed up to a client meeting wearing my best dark jeans, a crisp white…
I have to admit something that might sound odd coming from a man who's spent twenty-five years wearing nothing but leather-soled dress shoes to work: I've been watching the sneaker…