In my experience, urban outdoor furniture is usually repaintable or refinishable, but “easy” depends a lot on the material, the existing finish, and how much wear it has seen. A simple painted steel bench or wooden slat table can often be refreshed with basic prep: clean it well, sand or scuff the surface, remove rust or peeling coating, apply a suitable primer, and then use a durable exterior paint. For home patios or light-use public spaces, that can be a manageable DIY job.
However, urban furniture is not the same as a quiet backyard chair. It faces rain, UV, pollution, salt, heavy use, and sometimes vandalism. Powder-coated aluminum or steel may look easy to paint, but it needs proper scuffing and an etching or bonding primer so the new coating grabs. Wood needs sanding and a moisture-resistant finish. Plastic and resin can be tricky because many paints peel unless you use an adhesion promoter. Wicker, rattan, and composite materials may need specialist products. Concrete or stone is generally not “repainted” in the usual sense, though it can be cleaned and sealed.
So yes, it is often possible to refinish urban outdoor furniture, and small touch-ups are usually straightforward. But for busy commercial streets, parks, transit stops, or pieces with a factory powder coat, I would not call it a quick weekend job. Professional refinishing is often worth it because the prep and coating quality determine whether the result lasts one season or several years. The keys are correct surface prep, the right exterior-grade product, and realistic expectations about maintenance.