The expression "dressed with a needle" means that the thing is new, not worn, just from the tailor’s needle, recently sewn, sits impeccably. Later, an extended interpretation of this expression arose: a man is dressed “in fashion”.
There were times when clothing stores did not exist, so commoners sewed it themselves from homespun fabrics or bought in the markets, and noble and wealthy people ordered from tailors. The tailor's work was complicated and time-consuming: in order to sew a dress according to the figure in those days, great skill was required. Tailors were very attentive to their customers and tried to do the job with the highest quality, so that people would turn to them in the future.
The best craftsmen were those who sewed things without multiple trying on, so to speak, "the first time." And this requires a lot of experience. It was in the case when the customer came to the first fitting, and the clothes immediately came up to him, without requiring additional work, they said “clothes are like a needle”, which meant - sewn the first time.
Of course, there were very few specialists of this level. Therefore, almost all tailors, trying to preserve their clientele, constantly worked on their skills, honing him all the time.
Today, the phrase "dressed with a needle" characterizes those people who wear expensive, fashionable and beautiful clothes that sit perfectly - regardless of whether it is sewn to order or bought in a store.