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

How Asking One Simple Question Before Buying Clothes Changed Everything for Me

You know that feeling when you’re staring at your closet full of clothes thinking you have absolutely nothing to wear? Yeah, I lived there for years. Had a closet stuffed…

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June 26, 2025 British Style Fit & Tailoring Shopping Style Advice Wardrobe Basics

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 –…

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June 24, 2025 British Style Fit & Tailoring Shopping Style Advice Wardrobe Basics

I Wore Only Black and White for a Year and Here’s What Actually Happened (Spoiler: It Wasn’t What I Expected)

So I made this completely ridiculous bet at a dinner party three years ago, and honestly? It changed how I think about wardrobes more than any other experiment I’ve done.…

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June 19, 2025 Fit & Tailoring Shopping Style Advice

Why Men’s Clothing Sizes Are a Complete Disaster (And My Hard-Learned Shopping Survival Guide)

I’ve got three medium polos hanging in my closet right now – same brand, same style, bought six months apart. One fits Jackson perfectly (he’s seven), one makes me look…

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June 17, 2025 Style Advice

Let My Wife Dress Me for a Week (Got a Promotion and Learned I’m Style-Blind)

So there I was last Sunday morning, drinking coffee while Sophie colored at the kitchen table and Jackson played on his iPad, wearing what I genuinely thought was a decent…

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June 11, 2025 Style Advice

Why I Stopped Believing in “Color Seasons” and Started Actually Looking Good

So there I was in Target’s men’s section last Tuesday, holding two identical polos – one in what I’d call “generic blue” and another in this sort of dusty olive…

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June 6, 2025 Style Advice

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…

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June 5, 2025 Style Advice Wardrobe Basics

15 Pieces That Actually Matter: Building a Wardrobe That Works

So last year my closet basically exploded. Not literally – though that would’ve been cooler – but I had one of those moments where you look at your clothes and…

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June 4, 2025 Style Advice

Dad vs. Dress Code – Figuring Out What to Wear When Nobody Knows the Rules Anymore

Last week I’m grabbing lunch with this guy Dave from my old job, and I swear I thought he’d lost a bet or something. Guy shows up looking like he…

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June 3, 2025 Fit & Tailoring Style Advice

How I Learned to Look Better Than the Guy Wearing the Same Exact Outfit

You know what happened to me at the Kroger last week? I’m standing in line at the deli counter, waiting for my usual half-pound of turkey (Jessica makes these killer…

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