Silks

[Dave Paprocki]

Some fine (expensive) clothes. Term was popularized by members of Duke Ellingtons Band -- the Duke being a stickler for well dressed musicians.

[Rihanna]

short for silk boxers

[Vania]

Silks, or the silks, is a slang term used to describe an item of great worth--typically dropped from a boss in an RPG video game.
The term originates from The Silks of the Victor, the unique Ancient Plate from Blizzards masterpiece Diablo II. Legend holds that this item could only be dropped from Diablo himself, but only few mortal men have had the mettle to challenge and defeat the beast.
In some circles, this term has been expanded to describe items acquired in real life.

[Mark Zuckerberg]

AKA tall flags

[Cami]

to eat breakfast at your favorite local restaurant

[Britney]

Silks in Horse Racing. The name given to the blouse and cap worn during a race by the jockeys. Each jockey wears the colors of the owner of his horse. Harness racing drivers wear jackets.