Back in my student pilot days, while I was marking time waiting to be old enough to take my flight test, I had only my solo cross country to complete. I recall asking my instructor on several different days if the weather was good enough to fly my cross country. His reply was always, "I don't think so", so I just flew circuits or in the practice area instead.
Next time, I asked my instructor if the weather was good enough, and he said "I don't think so". As I turned away to contemplate more circuits, another instructor whispered to me "check the weather yourself!". I did, and is was perfectly fine for the intended flight. (This was decades before the information age, when checking weather actually required effort)
Not wanting to affront my instructor, I none the less, returned to him, and said "I just checked the weather, and it seems fine for my flight". He cheerfully replied, "Great, have a great flight then!".
I learned to listen to advice, but to gather my own information, and make my own decision.
The flying school routes for cross country flights were carefully planned to be in well covered weather reporting areas. There are, and are still large areas in Canada where weather information is sparse, and really good decision making is required.