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November 11, 2025 British Style Fit & Tailoring Shopping Style Advice Wardrobe Basics

How I Learned to Layer Like a Pro (And Why Every Guy Should Master This)

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…

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November 10, 2025 Style Advice

The Real Working Men Who Haven’t Given Up on Looking Good

Last Tuesday I found myself in a staff room in South London that smelled like instant coffee and desperation, watching this English teacher named Tom get ready for what he…

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November 8, 2025 British Style Style Advice

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,…

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November 7, 2025 British Style Style Advice

Why British Summer Dressing is Like Trying to Date Someone Who Won’t Text You Back

There's this moment that happens every year in Britain when the temperature hits like 22 degrees and suddenly everyone loses their absolute minds. I saw it go down just last…

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November 4, 2025 Style Advice Wardrobe Basics

The Dad’s Guide to Not Looking Like a Disaster in a Suit

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…

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October 6, 2025 Fit & Tailoring Style Advice

I Changed One Thing About Every Outfit for 30 Days and Everyone Started Asking What Was Different

So there I was last month, staring at my closet like it had personally offended me. Which, honestly, it kind of had. My friend Sarah had just told me at…

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October 5, 2025 British Style Fit & Tailoring Shopping Style Advice Wardrobe Basics

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…

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September 30, 2025 Style Advice

What I Learned From Professional Stylists About Why Most Dads Look Terrible (And It’s Not What You Think)

So there I was last Tuesday night, standing in line at Jackson's school pickup, when I noticed Mike from the PTA wearing what had to be a $200 shirt. You…

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September 29, 2025 Style Advice

I Watched Every Guy at This Coffee Shop and Realized We’re All Just Following Different Style Rules

So I’m sitting at this coffee place in Lincoln Park last Tuesday, supposed to be working on some campaign briefs but honestly just procrastinating hard and watching people walk by.…

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September 28, 2025 Style Advice

My Style Rock Bottom: How I Clawed My Way Back From Stained Sweatpants and Actually Learned Something

I need to tell you about the most embarrassing moment of my adult life, and it happened on a random Wednesday morning about three years ago. I was getting ready…

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