Look for seasonal deals.
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If you're out to get a deal on something for yourself, it pays to think in product cycles. Since fashion works a season ahead, for instance, it's already getting late for a lot of winter items. That means it's an opportunity to look for items that would be costly otherwise. Thoreson says in particular to keep an eye out for a solid pair of boots. "Whether technical and hiking-inspired, or a version of a dress shoe, like a brogue or wingtip pattern in a boot form, more and more guys are wearing boots with suits now," he says. As the season to buy winter-weather footwear is quickly coming to an end, that also means sellers will be looking to clear out inventory. "[Boots] can run you several hundred dollars at full price," Thoreson says, "so this is exactly the moment to be looking for a deal."