Getting your temperature up in a warm environment over hours is easy: a low net heat output increases temperature over time to pretty high. Keeping it up in freezing temperatures is hard because the body loses the heat so fast.
Your body is actually very good at keeping you warm enough under a very wide range of temperatures. As with everything with humans, if you want it to be better at it, you can “practice” by progressively doing things that make you chilly. If you are active, you can last pretty much indefinitely in a t shirt and shorts in above freezing temperatures. Just go in/warm up when you start to shiver: that means your body isn’t keeping up with your core temperature. Eventually, you wont ever start to shiver. Source: I went year round in T shirt and shorts in freezing/close to freezing temperatures while being outside for hours at a time.
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