i would probably forget about timberland stuff - they are way overprice for the performance they give. other brands like Hi-tec, Columbia and Soloman give much better value and they are brands that many mountainers and outdoor people swore by because of their design.
you might want to look at a 3-Season (Spring, Summer and Autumn) mid cut shoe - these will take you into the snow (unless you are doing extensive hiking in snow) and still remain quite usuable in Singapore. Some boots are solely for winter/mountain use and will be very useless in tropical singapore.
assuming you just need a pair of good shoes for light hiking in winter conditions, things i will look out for:
1. Water proofing design - It all depends on the stiching and general construction of the shoe - check the "bellow" around the tonge. Goretex layered boots can also leak. Goretex is expensive, there are similar cheaper membranes around. Alternatively is to get real leather boots and deep wax them. Oh yeah, DONT EVER :nono: deep wax shoes with goretex or similar membranes. you will just be sealing the pores of the leather and defeating the purpose of the membranes!!
2. Sole rigidity - you don't want something that flexes too much - actually SAF combat boots have a little too much lateral and horizontal flex for real heavy trekking and winter use. Timberland's casual hiker shoes have a lot of flex and is suitable for street walking and very light trekking like in MacRitchie

Look for something that has a torsion bar embeded in the sole - tradtional boots have them in steel, but it will not pass the airport sensors. Nowadays they make them with very hard plastic. This actually helps to lessen foot fatigue in long hikes.
3. three-quarter cut just incase you are in ankle deep snow.
4. Go for a design that has a clean toe cap e.g. SAF boots. Some fancy designs have a flat top with stichings ala deck shoes. These just serve as platform to hold snow and water.