One of the ugliest semi=auto pistols ever made is the Webley and Scott Self-Loading. This pistol entered service in 1913 with the Royal Navy, and eventually accepted by the Air Corp and other services and ended up staying in service until the early 1950's. It's square receiver and stock and long thin barrel make for an ungainly and uncomfortable looking package. In addition, there is a large, odd looking grip safety about 2/3rd of the way down the grip.However, reports are that this was a reliable pistol.
This single action, locked breech design. It had a "half-cock" type safety. Another unusual feature was the ability to partially push a magazine into a locked position. This allowed the pistol to become a single shot pistol with the ability to hand feed single cartridges into place. Why this would be practical... no clue.
The caliber for this pistol is .455, technically the .455 Webley and Scott Auto, although this is not the same as the revolver round. The cartridge is semi-rimmed and shoots at a measly 750 feet per second. It's a slow, but big bullet that apparently had plenty of stopping power.
The pistol was also made in .38 Service Round, with a 200 grain bullet for the British. Also, export models were made in 38 Super, and a compact version in 32 ACP and 25 ACP.