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When Is the Best Time To Do Your Holiday Shopping?

Holiday shopping used to be relatively simple. Consumers celebrated Thanksgiving with a traditional turkey dinner, went to sleep, and then got up early for the big deals on Black Friday, the one-time biggest sales day of the year.

However, over the past few years Black Friday has become not just a day, but also a season. Some retailers, including online colossus Amazon.com (NASDAQ: AMZN), barely waited until Halloween had ended before kicking off its holiday sales. In addition to early November promotions, consumers now must contend with big chains offering sale events on Thanksgiving, and the online sales bonanza on the Monday after Thanksgiving known as Cyber Monday.

It's no longer an easy thing to know when to get the best deal on what. That has confused consumers and led to a greatly extended shopping season. In fact, 31% of holiday shoppers started shopping before November, according to research from Adobe, a 5% increase over 2015. In addition, 27% will start buying holiday gifts and other items before Thanksgiving while only 22% will wait until after Black Friday to begin shopping.

Starting early may help spread out expenses, but there are specific days when consumers are likely to get the best deals overall and others when it's better to buy certain items. It's not an exact science, but knowing when the biggest savings are offered should help you save some money.

Amazon has been adding warehouse help to get ready for the holiday season. Image source: Amazon.

When should you shop?

In general, shopping before Black Friday makes little sense. In many cases, retailers, including Amazon, have simply repurposed their regular weekly sales labeling them as special holiday deals. The only exception for this is if an early November sale offers an item you need for use now at more than 20% off its normal price. You might get a better deal by waiting, but if you need a new laptop, printer, or winter coat, you have to balance actually being able to use the item versus the potential to pay a little less later in the season.

When it comes to the best day to shop overall, of the three big named shopping days, Black Friday actually offers the worst deals.

"If you were to pick just one day to shop, our research shows that it is not Black Friday that you should choose, but Thanksgiving," DealNews.com wrote. "Last year 38% of the deals published on Thanksgiving were Editors' Choice deals, compared to only 31% for Black Friday -- making Thanksgiving the deal champ. And not to be outdone, Cyber Monday boasted 36% Editors' Choice deals."

Thanksgiving may be the best day to shop, but Black Friday and Cyber Monday have their share of top savings as well. In a broad sense, Thanksgiving Day through the following weekend are the best days to shop at department stores and big box retailers, according to Real Simple.

Cyber Monday offers the best online deals, with the caveat that Amazon specifically stretches out the holiday season throughout November and December. Finding the best deals on the online retail leader requires vigilance as some of its best offers are "Lightning Deals," limited-time offers that last only a few hours.

While the big three shopping days offer the best deals overall, if you want big-ticket items like televisions, furniture, and jewelry you're better off waiting until Dec. 21 or even later, Real Simple wrote. If you want a specific TV or other item, playing holiday chicken might mean not getting it, but if you're looking for "a big TV for the living room," or a new kitchen table, waiting until stores get desperate is the best strategy.

One thing that could change all of this

All of the advice above should prove valuable if the holiday season goes as expected. If, however, sales start slowly and the Thanksgiving through Cyber Monday period does not produce the desired results, retailers may panic, sending prices lower.

That's unlikely to happen on a large scale, but it's certainly possible that some chains will not have the early results they hope for. If, for example, a struggling chain like Sears has a slow start to the season, it may ramp up its sales in order to not get stuck with inventory. That's hard to plan for when it comes to buying gifts, but it could lead to buying some wanted, but not-exactly needed items for yourself.

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Daniel Kline has no position in any stocks mentioned. He's probably not buying you a Christmas gift. The Motley Fool owns shares of and recommends Amazon.com. The Motley Fool recommends Adobe Systems. Try any of our Foolish newsletter services free for 30 days. We Fools may not all hold the same opinions, but we all believe that considering a diverse range of insights makes us better investors. The Motley Fool has a disclosure policy.