Time heals all and heels hurt to walk in
But they go with the clutch that you carry your lip gloss in

from Drake (Ft. Swizz Beatz & T.I.) – Fancy Lyrics on Rap Genius

Meaning

A play on the common saying “time heals all”. Drake puts his trademark spin on it by trying to relate to the girls he’s talking to, instead of being a cocky womanizer.

The reason she wears her heels is strictly because they match her outfit; even though it will be painful, she does it to fit an arbitrary standard of beauty. This is rather ironic because the song is Drake’s ode to strong, independent women, but someone who isn’t confident enough to wear something she is comfortable in doesn’t fit that type.

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