Everyone has a different threshold of pain. That being said, I would simply recommend putting your boots on and seeing how your bruises align with the pressure points you know you're going to apply with the boots. The bruising could be completely clear and no discomfort from your essential equipment. Additionally, being active is one of the best ways to aide healing of a contusion as the increased blood flow and muscle contractions help move the swelling out of the impacted area. One piece of important advice is to not take any NSAID pill for pain, i.e. aspirin, ibuprofen, naproxin.
Use Tylenol or its generic derivative and you can control the pain. You also should have plenty of snow to cool it down during breaks you may take and afterward. Lastly, I'm assuming from the pictures that this is higher on the shin, and looks to be an impact injury as the boundary of the bruise is pretty well defined. You will possibly feel a similar pain to "shin splints" that happens to athletes impacting hard surfaces over a prolonged period of time. In your case, once the muscle is warmed up and used, this feeling should diminish. However, this discomfort will be there each time until it has healed since the injury has created a natural pocket to attract lactic acid. End of the day, you RX is skiing!! Have fun!