These are the best telephoto lenses for street photography when you want discreet distance, flattering compression, fast and reliable autofocus, and creamy separation for candids, layered city scenes, silhouettes, reflections, and detail B-roll—without crowding your subjects—and here’s what to look for as you buy: prioritize quick, quiet AF (linear/USM/LM/STM), compact weight/balance for day-long carry, strong flare/ghost control for point lights and neon, honest edge sharpness at mid apertures, stabilization (IS/VR/OSS or strong IBIS) for dusk hand-helds, and minimal focus breathing if you film; 85–135mm primes are classic “stand-off” street lengths, 70–200mm covers everything from alley abstracts to compressed crosswalks, and 100–400mm lets you carve distant layers from across a boulevard or river. Full-frame standouts: Sony FE 85mm ƒ1.8 (light, fast, affordable), FE 135mm ƒ1.8 GM (buttery isolation with bite), FE 70–200mm ƒ4 G II (compact, macro-ish close focus for signage), FE 70–200mm ƒ2.8 GM II (event-ready speed), and FE 100–400mm GM (tight skyline layers); Canon RF 85mm ƒ2 Macro IS (stabilized, close-focus utility), RF 135mm ƒ1.8L IS (luxury street tele), RF 70–200mm ƒ4L IS (tiny for class) and ƒ2.8L IS (night-friendly), plus RF 100–500mm L for distant geometry; Nikon Z 85mm ƒ1.8 S (neutral, tack-sharp), Z 135mm ƒ1.8 S Plena (sumptuous rendering), Z 70–200mm ƒ2.8 S (stellar optics/VR), Z 70–180mm ƒ2.8 (compact flexibility), and Z 100–400mm S for waterfront compression; L-mount: Sigma 90mm ƒ2.8 DG DN C (pocketable short tele), Panasonic S 70–300mm OIS (balanced, close-focus), Sigma 100–400mm DG DN OS (light long end). APS-C and Micro Four Thirds gems: Fujifilm XF 90mm ƒ2 (razor portrait/candid tele), XF 50–140mm ƒ2.8 OIS (workhorse), XF 70–300mm ƒ4–5.6 OIS (light layer-carver); Sony E: Sigma 56mm ƒ1.4 DC DN (tiny bokeh beast), Sony E 70–350mm ƒ4.5–6.3 G OSS (daylight reach with OSS), and Tamron 70–180mm ƒ2.8 on A6xxx for evening speed; Canon RF-S 55–210mm IS STM (compact, stabilized), Nikon Z DX 50–250mm VR (surprisingly crisp), Micro Four Thirds: OM SYSTEM 40–150mm ƒ4 PRO / ƒ2.8 PRO (weather-sealed, featherweight coverage), Panasonic 35–100mm ƒ2.8 II OIS and Leica 50–200mm ƒ2.8–4 OIS (balanced, flare-tough). Practical buyer tips: pick 85mm for people at conversational distance without intrusion, 135mm for deep compression and clean backgrounds, 70–200mm ƒ4 when you walk all day, and ƒ2.8 versions for night markets and events; a 100–400mm is brilliant for isolating patterns, signage stacks, and waterfront layers from afar; standardize filter diameters for one slim CPL (use sparingly—too much kills reflections) and a light diffusion filter if you like glow; used EF/F 85/1.8, 135/2, and 70–200/4 IS remain budget-savvy tele street tools via adapters. Tele-street shooting tips: work in AF-C with subject/eye detect and a limiter, pre-focus to crosswalk zones and let people walk into your plane, shoot near wide open then stop 1/3–2/3 stop for eyelash-sharp faces and gentle rolloff, keep shutter speeds honest (≈1/250–1/500s for walkers; 1/1000s+ for cyclists), brace on poles/doors or use a monopod for long glass, backlight for rim-lit outlines and steam glow, watch speculars—angle a few degrees to avoid self-reflection in glass, and layer foregrounds (railing, signage) for depth; for nights, expose for faces/bright signs, enable anti-flicker if available, and use stabilization to hold steady between motion peaks; be respectful and read the room—distance helps candid authenticity—and when your telephoto combines decisive AF, strong coatings, and steady handling, your city stories come back sharp, graphic, and beautifully composed from a comfortable, unobtrusive distance.