"Right now, boots are going to be at their most expensive," says Andrea Woroch, savings expert with CouponSherpa.com. "When everyone is thinking about buying boots, that's when prices will be the highest."
When to expect better deals: At the holidays. You'll start seeing deals on Black Friday and Cyber Monday, she says. And check for deals in the weeks leading up to Christmas, she adds.
"In January and February, you'll start seeing anything that didn't sell at the holidays marked down in the clearance section," Woroch says. That's when "retailers are clearing out for spring merchandise."
What is on sale this month: "Summer sandals, peep-toe pumps and anything that was big for summer," Woroch says. Sizes will be limited, but you can find huge deals -- 60 percent to 80 percent off, she says.