The speaker is a tailor's son, and the poem opens with a small, funny image: he and his clothes go out together, almost like two companions. He heads to a play or visits places that "understand wit without money," meaning spots where cleverness and good conversation count for more than a full wallet. The title suggests his clothes may be the best thing he has, since his family's trade gives him a smart appearance even if he can't pay his way.
The ending shifts the tone. He compares himself and his clothes to ships that sail out to "fetch the queen of melancholy / for a lost card." The image is odd and a little hard to pin down, but it suggests a grand, elaborate effort that brings back only sadness, and for something small and misplaced. The mood is wry and self-mocking, with a quiet ache underneath. The speaker seems to be dressing up his poverty with style and humor, yet the sadness still arrives.