This is a question I get asked a lot by those starting to learn to draw. Holding a pencil for drawing is similar in a way to holding a pen for handwriting in that there are ways that get better results, however it is a personal choice. Just like handwriting we all have a unique style so I think the best advice is however it feels best.
You can work out of doors at any time of the year if you go prepared. I offer a few tips on how to be prepared. What you will need will depend on the medium you are using, drawing outside is relatively simple equipment-wise but painting is a bit more complicated.
Drawing outside is a pleasure and gives so many advantages such as the quality of the light, seeing in context and in three-dimensions. All you really need to draw outside is a good hard-backed sketchpad and two – three drawing pencils in different grades of B.
A more developed sketch or drawing might require sitting rather than standing and this case you might want to bring a simple folding camping stall and perhaps a lightweight drawing board. Drawing outside in the summer will require water and suntan lotion, you may also want to wear a hat because when you are looking down the back of your neck can get burnt without realising!