There is an old saying in the shopping world that says that if you want to find the best deal on something, you want to wait until the middle of its season to do so. In most cases, this could not be any more true. And when it comes to seasonal clothing such as hats, gloves and shorts, you are going to find the best deals of any point in the year at the midway point in the most relevant season. This is because the early part of the season sees the mad rush of the folks who did not plan ahead for it, and the later part of the season only sees the occasional liquidation sale of the stuff that nobody really wants in the first place.
At the first stages of any season, there are going to be a lot of people who simply did not remember that the season was starting up soon. So naturally, they are going to flood into the stores, intent on getting what they want no matter what the price might be for it. And of course, this is the time when the selection will end up getting snapped up, and the prices will be at their worst. So if you have any seasonally appropriate wear during this time, use it until it wears out, to avoid paying the “can’t plan ahead” price for it.
At the end of the season, the vultures have essentially picked the aisles clean of the best stuff for the season. While you might find some deep discounts, they will usually be on something that is out of style (or just plain ugly), does not fit very well, and is on the shelf because they simply could not find anybody who was willing to buy it. At this point, it is really too late, and you might as well just stock up for next season and suffer for the remainder of the season.