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Author: Jacob

Home Author Archives: Jacob
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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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 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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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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August 11, 2025 Style Advice

Why Your Style Choices Are Adding 10 Years to Your Age (And How I Fixed Mine)

So this is going to sound harsh, but I watched my dad's older brother completely age himself out of relevance at a family gathering a couple years back, and it's…

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August 1, 2025 British Style Fit & Tailoring Shopping Style Advice Wardrobe Basics

How I Learned to Stop Overpacking and Actually Enjoy Traveling Light

You know that specific moment when you realize you've been doing something completely wrong for years? Mine happened at O'Hare, standing behind this family of four in the security line.…

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July 24, 2025 Shopping

I Spent Two Weeks Comparing Target vs Walmart Clothes and the Results Actually Shocked Me

So there I was at 7:30 in the morning, standing under those soul-crushing Walmart fluorescent lights, stuffing $12 chinos into my cart while trying not to make eye contact with…

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July 17, 2025 Style Advice

Why Most Men’s Style Advice is Actually Making You Dress Worse (I Should Know – I Used to Follow All of It)

Last month this guy Mike from Cleveland sent me an email that honestly made me feel a little sick to my stomach. He'd been following men's style advice religiously for…

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