wearing a stripe

To have a rank of some significance in an organization, to have ascended above the rank-and-file members of the group, and have more responsibility and more status.

Joe used to be an unpaid intern, but when Gus left, Joe got promoted and now he's wearing a stripe.

Chris Moltisanti used to be a little shitheel till he got made. Now he's wearing a stripe.

the best time to wear a striped sweater

Is all the time

-Spongebob Squarepants

Spongebob Squarepants Singing
*The best time to wear a striped sweater is all the time*

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The best time to wear a striped sweater

All the time

I'd like to call this little number "Striped Sweater." *queue music* The best time to wear a striped sweater ... Is all the time....
One with a collar... Turtle neck... thats the kind. Cause when you're wearing. That one... speical...sweater