My Decade-Long Education in Outlet Shopping: From Teenage Sucker to Skeptical Bargain Hunter
I need to tell you about the day I learned that outlet shopping isn’t what I thought it was, because honestly, it took me way too long to figure this…
How I Learned to Dress for Job Interviews After Some Pretty Spectacular Failures
I walked into that law firm interview feeling pretty confident about my charcoal gray suit – you know, the one I’d spent way too much money on at Men’s Wearhouse…
I Found J.Crew’s Hidden Price System and It’s Been Saving Me Money for Years
I stumbled onto something weird at J.Crew about two years ago, and honestly, I’m still not sure if I’m supposed to talk about it. But it’s saved me probably close…
That Time I Tried to Dress Like an Italian and Failed Spectacularly (Plus What Europeans Actually Do Better)
So I’m standing outside this café in Florence three years ago – this was during my “maybe I should dress more European” phase, which, spoiler alert, didn’t go great –…
My Ongoing Battle with H&M’s Bizarrely Inconsistent Sizing System
So there I was last Tuesday, sitting at my desk in our Chicago office with exactly three different article deadlines breathing down my neck, when my editor shoots me a…
Gap vs Old Navy vs Banana Republic: What’s Actually Worth Your Money
I made a terrible financial decision last week. Wandering through the mall after a haircut, I ended up at Banana Republic because they had one of those “40% off everything”…
Why I’m Downsizing From 31 Pairs of Shoes to Just 5 (And You Should Too)
So I’ve got this embarrassing confession to make. Last weekend, I finally counted all my shoes. Not like a rough estimate or “yeah, probably around fifteen pairs” kind of count,…
My Dad’s Terrible Style Is Suddenly Cool (And I’m Having an Identity Crisis)
Last month I caught myself trying on a windbreaker at a thrift store in Lincoln Park that was basically identical to one my dad wore throughout my entire childhood. Same…
My Yankees Cap Has Seen More of the World Than Most People I Know
There’s this Yankees cap sitting on my dresser right now that honestly deserves its own passport. Thing’s been with me longer than most friendships, and I’m pretty sure it’s more…
Why I Started Taking Every Shirt to My Tailor (And You Should Too)
Look, I used to be one of those guys who thought alterations were for rich people or wedding suits. Like, why would I spend extra money on clothes that should…