Singapore was chosen as a base by the British in 1921 (June 16th to be exact) after it was realized that Japan was becoming expansionist and that Hong Kong was essentially undefendable. However, the combination of a liberal Labor government and the poor economy meant little was done towards actually building a base there.
By 1926 the Committee for Imperial Defense finally drew up initial plans for a base there and its defense. Included were the installation of a number of medium and heavy coastal defense guns including 3 15" guns.
These plans languished without any real committment by Britain's Labor government until 1932 when the planning was finalized. Included in the planning was a document stating that gun batteries would be the primary coastal defense system with aircraft providing additional support.
In 1935 the British finally started work on installing coastal defenses and building a naval base at Singapore. The RAF also began building bases at Kota Bharu and Kuantan in the north of Malaysia as well. These bases were to provide airfields for aircraft for maritime patrol and early detection of enemy convoys. However, the RAF paid little attention to the locations outside their suitability as airfields and the Army upon inspecting the sites found them undefensable in the event there was a ground war.
In 1937, for the first time apparently, the British started looking at the possibility of having to defend the 1000+ miles of Malay coastline against invasion. Major-General W G S Dobbie determined that the Japanese could invade along the East coast of Malaysia virtually year 'round and that the period from October to March was particularly vulnerable due to frequent overcast weather that made aerial reconnissance difficult. Kota Bharu was marked as the most likely landing site in Malaysia of a Japanese invasion (it was and that is where they landed their primary forces). This report was ignored in Britain (how usual).
In 1938 General Dobbie sent a second report based on local maneuvers that the Jungle from Johore and into Southern Malaysia was not "impenetrable" as the Imperial Chiefs of Staff believed. It too was ignored.
By 1939 all that had been done to protect the vulnerable land side of Singapore was the construction of some machinegun emplacements with a mere 60,000 pounds allocated to the project.
With increasing likelihood of a Pacific war, New Zealand and Australia both urged the Imperial Chiefs of Staff to move a fleet to that area before the war began. Nothing happened on this either.
In September 1939, the British sent an additional Indian infantry brigade with a mountian artillery regiment and two bomber squadrons (Blenheims) to Singapore. Also, the possibility of building up a 6 month supply of food stocks for the military and civilian population was "investigated" (we all know where that went

).
At this time Singapore had 5 regular infantry battalions, 2 territorial infantry battalions, two coastal artillery regiments (static), three anti-aircraft regiments and 4 fortress engineering companies in addition to the Indian units just arrived. There were 6 RAF squadrons with 58 aircraft in place.
The general atmosphere remained one of placid ignorance for the most part. Social events and a peacetime military attitude remained in place. Social events for officers and members of the civilian administration still took precendence over any wartime planning or training. Local merchants and plantation owners still resisted any use of their land for training by the military and if any such maneuvers were carried out strong protests and demands for payment for damages were made to the government immediately.
In February 1941 the Australian 8th Division arrived and more troops were said to be on the way. Lieutenant-General A E Percival became Singapore's and Malaysia's overall commander. Described as a good staff officer with little leadership or personal ability he was a poor choice for command.
One of Percival's first actions on arriving in Malaysia was to order defense installations built at the Northern RAF airfields (that were "indefensible" by Army reconning). He also found that most pre-war defense planning was exactly that...planning nothing more. Little had been done to improve the defense of Singapore or Malayia since 1937.
The RAF commander, Sir Robert Brooke-Popham, in Singapore turned down Hurricanes in early 1941 suggesting that "We can get on alright with Buffaloes out here...". Thus, the RAF sent what would be eventually 5 squadrons of Buffaloes (167 were sent, with 20 lost in accidents during peacetime) to Singapore as part of the last minute build-up of forces there. To British credit, they did believe they would primarily face the Ki 27 Nate or A5M Claude (both of which
were inferior to the Buffalo) rather than the Ki 43 Oscar or the formidable A6M Zero.
By October 1941, with the prospect of war immenent in the Pacific, the British sent the
Prince of Wales and
Repulse (the carrier
Indomitable was also supposed to go but was damaged by grounding) to Singapore. On land, the 9th Indian Infantry Division (8, 28th Bdes), the 11th Indian Infantry Division (6 and 15th Bdes), 28th Ind. Inf Bde under III Corps defended Malaysia on the mainland, while in Singapore the 8th Australian Infantry Division (2 Bdes), the 12th Ind. Inf Bde and 2 Malay Infantry Brigades were now garrisoned. Almost all of these troops had had little real field training and some units like the 11th Indian Division were virtually untrained.
This was the state of the defenses at Singapore in December 1941.