How to photograph skyscrapers and skylines
One problem separates an amateur skyscraper photo from a good one, and it is geometric. The rest is light, distance, and the rules of the place you are standing in.
The converging verticals problem
Tilt a camera up at a tower and its sides lean inward, so the top comes out narrower than the base by an amount no real building is. This is keystoning: the sensor is no longer parallel to the facade. The wider the lens and the closer you stand, the worse it gets.
Three fixes. Step back and put on a longer lens: from three or four blocks away at 85 mm or 135 mm you barely tilt at all. Keep the camera level, frame in the sidewalk you did not want, and crop the bottom off, which costs resolution and buys straight lines. Or correct it in software, with Lightroom's Transform panel or Photoshop's Perspective Crop; that stretches the top of the frame, so leave margin around the crown.
The proper tool is a tilt-shift lens. Shifting the front element upward moves the image circle instead of the camera, so the sensor stays parallel and nothing converges. A 17 mm or 24 mm tilt-shift is expensive and manual focus, which is why most people crop instead. If you own one, this is what it is for.
The blue hour
Roughly twenty to forty minutes after sunset the sky still holds color and the building lights are already on. That overlap is when most good skyline photographs are taken. Earlier the windows are dark against a bright sky; an hour later the sky is black and the lit windows blow out. Be framed before sunset and keep shooting, because the balance shifts every few minutes.
Across water, or from a bridge
A skyline needs distance. Among the towers you see walls; a mile back you see the shape of the group. Water gives you that distance with nothing in the way, and a reflection that doubles the lights. Hence the standard views from across a river or harbor: Brooklyn Bridge Park for Lower Manhattan, North Avenue Beach for Chicago, the Kowloon promenade for Hong Kong Island.
It also needs a foreground, or the picture is a stripe across the middle of the frame: a railing, a moored boat, rocks at the waterline. Bridges work the same way and add elevation, but check whether the one you picked vibrates when traffic crosses, because a two-second exposure on a shaking deck is unusable.
Up from the base
The convergence you fight in a portrait of a whole building is useful once it is the subject. Stand at the base, use a 16 mm or 20 mm lens or a phone's ultra-wide, point straight up and center the frame so the lines run to one vanishing point. Two or three towers around a plaza beat one. Symmetry makes it read as deliberate; a slight lean reads as a mistake.
Details, abstracts and reflections
A long lens isolates a facade pattern. At 200 mm the mullions and repeated windows flatten into a grid and a curtain wall becomes a graphic. Look for where the pattern breaks: a corner, a setback, the seam between two cladding types. Art Deco towers give you more of this than glass boxes.
Reflections in a neighboring tower's glass are the easiest strong frame in a business district: an older building mirrored in a newer one, broken by the panel joints, dates both in one shot. The light has to be on the reflected building and not on the glass you shoot through, so walk the block early or late.
Tripods, shutter speeds and glass
Below about 1/60 second you need a tripod, and the blue hour at base ISO puts you well under it. Use a remote release or the two-second timer, switch stabilization off, and shoot f/8 to f/11. Many observation decks ban tripods, so check before you carry one up; without one, a beanbag on the handrail, ISO 6400 and a fast lens will get a night skyline.
Glass is the other problem on an enclosed deck. Press a rubber lens hood flat against the pane and the reflections go; a rigid hood works almost as well if you block the light behind you with a dark jacket. Shoot perpendicular to the glass and pick a clean patch, because deck windows are covered in handprints at eye level.
Law and access
Photographing buildings from public streets is generally allowed in most countries, the United States and the United Kingdom included: what is visible from public land can usually be photographed and published. Some countries restrict publishing images of buildings commercially. In France, Italy and Belgium a photograph of modern architecture for your own use is fine, while selling it needs permission from whoever holds copyright in the building, normally the architect or their estate. Stock submissions, prints and advertising are the exposure, not snapshots.
Private property sets its own terms whatever the law says. Plazas that look public are often privately owned and staff can ask you to stop. Observation decks ban commercial shoots without a booking and set the tripod conditions on the ticket. Drones are the strictest case: dense city centers are controlled airspace, and an aerial skyline needs a licensed pilot and clearance.
On September 3rd
Skyscraper Day is September 3rd, a reasonable excuse to go and shoot the towers in your own city: pick a deck or a waterfront view and work the blue hour. Ten other things to do on the day are on the celebration page, and the observation decks page says which of the highest ones are enclosed. For vantage points, start with New York, Chicago or the twelve vertical cities.