My novel 'Murder in the Fabric' is set in Melbourne in 2020. The preferred mode of transport is to don the hoodie and the dark glasses. Then get onto your bicycle, and move freely wherever you like in the city. There is nothing distinctive about pedalling that will give the forces of darkness a handle.
I'm a big fan of the Jack Reacher books. I have read almost all of them. Jack is ex-military, the quintessential outsider. He has a bank account somewhere, but not much else. Drifting from place to place, he encounters trouble, and deals with it. In the books, the Jack Reacher character is physically quite large. Large enough to stand out in a crowd. Of course the character goes back quite a while, and mostly he is in small towns in the mid-west of America. He doesn't carry a mobile phone, all transactions are in cash. If he checks into a hotel then he invents a new name each time.
In the modern surveillance state, how long would Jack last in a big city without being detected? Cameras on every corner, drones hovering overhead. He's off the digital transaction grid, so only the visual surveillance could get him. Facial recognition would be a big issue, so Jack might have to take to wearing a hoodie and dark glasses. No real problem. However there remains the issue of 'gait analysis'. Each of us walks in a distinctive way. Given Jack's size then his gait would be quite distinctive. Stay away from cameras, you say. The forces of darkness don't advertise their capabilities, but there is a view that gait analysis from satellite may be possible.
The subway is out. In Melbourne you have to get an electronic ticket. Each one is identified, and can be tracked. A cab has a surveillance camera. Cars have number plates. Once your car is tagged by one camera, it can be followed through the whole system. There are big advantages to tracking. Once a single camera grabs you, then wherever you go, the system will have you. A complete trace.
How long would Jack last? Maybe 30 minutes or so. The controversy over the film character, played by Tom Cruise is interesting in this context. A less physically distinctive frame has its advantages, he can move about more easily.
You want to move around a city without being detected? If you walk down a less crowded street then the cameras can get a good view of your face. Even with the hoodie and glasses they might have a chance. Best to find a crowd, and get yourself buried in deep in the middle of the crowd. Think one of those big pedestrian crossings in Tokyo, say Shibuya. The cameras will then be faced with the problem of occlusion - it's hard to break up the total image into faces. They might be able to follow you for a while, but as you move into bigger crowds, eventually they will lose you. Problem is, in Melbourne there are only two or three intersections crowded enough to evade the surveillance.
I look forward to Jack getting on the bike.