Am I booking flights too early or too late for Europe this winter?

I almost always book as early as possible but do watch fares for a month or so. I’m not so sure how I’ll be buying for my yearly trip in February due to current fuel increases. I usually have flights booked by now.

The current fuel price situation has changed airfares for an unknown time into the future. Traditionally, there would be sales on winter airfares starting this fall. Will that happen this year? Who knows.

A few things you can do. Track airfares ( which it sounds like you are doing) to get a sense of typical pricing. Explore different routings using gateway cities at both departure and arrival destinations. Take advantage of any frequent flier miles you may have.

Booking. I would encourage you to book directly with the airlines.

We always book 8-9 months in advance. Then if the price goes down, I call the airline, and almost always get a credit or refund for the difference in price. I'm not sure if is because we have the Delta AMEX credit cards or not. When we book with miles, we do get miles refund if the price in miles goes down. I'm not sure how the other airlines work.

I have a very clear idea of what a typical airfares is Singapore to London (my normal route for a Europe trip). It doesn’t generally vary that much unless it's a last minute booking.

I would typically book 3-4 months before, because I find if I book earlier than that I end up having to change dates. At the moment I have trips booked out until end of September.

At the moment fares are a bit higher than usual, but not crazy - at the upper end of what I would call the normal range.

As soon as we know we’re going, I start watching fares and schedules. When the price is about what I expected, I book. We almost always fly on Delta so if the fare drops later, I can reissue the ticket (or cancel, if necessary) and receive a credit for future travel. I always keep checking after I book to see whether the fare has decreased.
For example, last week I found a good fare and schedule for Seattle to Nice on January 31–March 3 and went ahead and purchased it. So I don’t really have a specific purchase window that I aim for.