Why I Stopped Looking Like a Silicon Valley Guy Playing Dress-Up in Tweed
I had this moment about two years ago when I was visiting my girlfriend's family in Vermont, and her dad showed up to breakfast wearing this perfectly worn-in Filson jacket,…
Why I Finally Admitted M&S Makes Some of My Favorite Clothes (And You Should Too)
Look, I need to confess something that would've made 28-year-old me absolutely cringe. I'm genuinely excited about Marks & Spencer basics. Not in an ironic way, not because I've given…
I Spent a Year Obsessively Tracking Every Piece of Clothing I Bought (The Results Were Brutal)
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…
Why I Still Wear Suits Even Though Everyone Thinks I’m Crazy
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 –…
Why I Started Wearing Sneakers to Work (And You Should Too)
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’ve Been Getting Smart Casual Wrong for Years (Here’s What Actually Works)
So I got this invite to a tech meetup last month and the dress code said "smart casual." My first thought? Great, another meaningless term that could mean anything from…
Four Years of Tracking My “Investment” Purchases – Here’s What Actually Worked
I had what can only be described as a complete meltdown in that store four years ago. Standing there with my credit card hovering over the reader, staring at a…
How I Finally Stopped Overpacking and Actually Fit Two Weeks in Europe Into One Carry-On
I used to be that guy who'd show up at the airport with a suitcase that weighed exactly 49.9 pounds because I was terrified of paying overweight fees, plus a…
How Silicon Valley Finally Learned That Hoodies Aren’t a Personality
The first time I stepped onto a major tech campus in Palo Alto back in 2018, I thought I’d accidentally walked into some kind of dystopian social experiment. Everyone—and I…
Why I Started Hunting Down the Last Real Menswear Stores (And You Should Too)
So this is gonna sound weird, but I’ve been thinking a lot about my grandfather lately. Not because he was some style icon or anything – dude basically wore the…