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8 Menswear Rules You Should Break

Sep 28, 2026 · 77.7K views

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DescriptionMenswear rules can help you dress better but following every rule doesn’t automatically give you great style. Most menswear rules exist for a reason. But there’s a big difference between knowing the rules and being controlled by them. After 15 years in menswear, I’ve learned that the guys who dress well aren’t the More
Menswear rules can help you dress better but following every rule doesn’t automatically give you great style. Most menswear rules exist for a reason. But there’s a big difference between knowing the rules and being controlled by them. After 15 years in menswear, I’ve learned that the guys who dress well aren’t the ones who follow every rule, they’re the ones who understand why the rules exist. So today, I’m breaking down 8 classic menswear rules. Understand them. Then decide when to break them and wear the damn clothes. --- 0:00 — 8 Menswear Rules You Should Break 0:26 — Rule #1: No White After Labor Day 1:33 — Rule #2: Your Belt Must Match Your Shoes 2:50 — Rule #3: No Brown in Town 4:10 — Rule #4: You Must Wear a Tie With a Suit 5:35 — Rule #5: Your Socks Should Match Your Pants 6:46 — Rule #6: Never Wear a Watch With a Tuxedo 7:59 — Rule #7: DB Jacket Should Always Be Buttoned 9:20 — Rule #8: Don't Use Your Jacket Pockets 10:56 — The Bottom Line 11:22 — BONUS RULE! Join the community as an insider: https://hespokestyle.com/newsletter-sign-up-youtube/ Shop essential menswear: https://hespokestyle.com/shop/ Browse the essential men’s style library: https://kit.co/hespokestyle/essential-library-of-men-s-style-books --- NEW VIEWER? START HERE https://www.youtube.com/playlist?list=PL3v2lRj6jZMeVLnSveZFagb48MaeGfAmo --- WHO AM I? GET TO KNOW ME BETTER: 5 Things I Regret Buying The Most https://www.youtube.com/watch?v=fEE5fURfTUk&list=PL3v2lRj6jZMdj2TKL6JezNG_

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