8 Menswear Rules You Should Break

He Spoke Style
He Spoke Style
1 Video View·Sep 30, 2026  #1 #2 #3

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.

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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!

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WHO AM I? GET TO KNOW ME BETTER:
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Reacting To Your Assumptions About Me
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