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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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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 27, 2025 British Style Fit & Tailoring Shopping Style Advice Wardrobe Basics

Those Tiny Details That Make Me Stop and Think “This Dude Actually Knows What He’s Doing”

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…

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September 23, 2025 Fit & Tailoring Shopping Style Advice Wardrobe Basics

Why I Tell Young Men to Skip the Sneaker Game (And How to Do It Right If You Won’t Listen)

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…

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September 19, 2025 Fit & Tailoring Shopping Style Advice Wardrobe Basics

How I Went From Cologne Disaster to Actually Smelling Good (And You Can Too)

The first time I bought cologne was junior year of college, and man, did I mess it up. Walked into Macy’s with no clue what I was doing, got overwhelmed…

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September 16, 2025 British Style Fit & Tailoring Shopping Style Advice Wardrobe Basics

Why I’ll Never Be “The Guy Who Always Wears X” (And You Shouldn’t Either)

So I’m grabbing coffee at this spot in Southeast Portland last week, minding my own business, scrolling through my phone and trying to decide if I really need another pair…

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September 9, 2025 British Style Fit & Tailoring Shopping Style Advice Wardrobe Basics

After Twenty-Five Years of Professional Dress, Here’s What Actually Matters (And What Doesn’t)

You know what's funny? I've been wearing suits to work for twenty-five years now, and I still see young attorneys making the same mistakes I made when I started. They'll…

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August 31, 2025 British Style Fit & Tailoring Shopping Style Advice Wardrobe Basics

My Hypebeast Spreadsheet Hit $17K and I Felt Empty Inside

I’ve still got that email saved somewhere in my Gmail archive from April 2016. Subject line was something ridiculous like “SUPREME DROP ALERT – BE READY!!!” with way too many…

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August 16, 2025 British Style Fit & Tailoring Shopping Style Advice Wardrobe Basics

I Spent Two Weeks Comparing $400 Common Projects to $40 Amazon Dupes

Man, I’ve got to tell you about this whole situation I got myself into with these sneakers. So there I was, probably three years into my style journey, still making…

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