Menswear Rules: Sometimes, Always, Never


There are a lot of rules in menswear and depending on who you ask, you might even think that there are too many rules. Yet, as silly and as outdated as some of these rules might be, there are a few that are still valid in today’s menswear scene. Such as my personal favorite, the sometimes, always, never rule!

This rule pertains to 3-button jackets and since this style is becoming popular again (as seen in my favorite show, Suits) I decided to shed some light on this classic menswear rule!


Starting with the top button, it’s sometimes appropriate to have this one fastened along with the middle one.

However, it’s always appropriate to have the middle button fastened because it pulls the jacket together at your natural waist. The rule generally states that you should always keep the middle button fastened, especially when you’re standing up.


Lastly, you should never button the last button, for two reasons. One reason is because it does not allow the jacket to drape properly. Second, it just makes you look like a beginner.

This rule also applies to 2-button jackets and waistcoats.


In short, the middle button should always be fastened, and the top button is totally up to you but the bottom button? Don’t even think about it!

As always, thanks for reading!

Yours truly,

Akil McLeod
The Dapper Advisor

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