Halloween remains more than three weeks away and some retailers have skipped right to Christmas. Technically, it’s the “holiday shopping season,” and that’s something that used to begin pretty clearly on Black Friday, the day after Thanksgiving. Then, that began to creep into actual Thanksgiving and then the week of Thanksgiving, before it became the month of November, and now, early October.

Retailers want to maximize their holiday sales even if that means lowering prices well before most people have considered what to get friends and family for whatever winter holidays they celebrate. Called “holiday creep,” it’s a relatively new phenomenon that exploded in recent years coming to its ultimate destination this year where the holiday season starts not long after the back-to-school season ended.

In theory, this helps retailers capture more dollars, but, in reality, it just magnifies the advantage held by Amazon (NASDAQ: AMZN) and other large retail players.

Deals where you don’t need them

About 13 years ago, I ran a very large toy store in Connecticut that did massive holiday business. We kicked off our seasonal sale on Black Friday, even though it was really the weeks after that when business picked up. In many cases, the items we sold at deal prices were not our bread and butter items that we sold all year. Instead, we brought in radio-controlled cars, planes, and helicopters in bulk where we could offer a good price and still maintain margins. We did similar things with model train sets, dollhouses, toys of all kinds, and slot car sets (an item that sold well for the holidays but barely moved the rest of the year).

In addition, we brought in a large selection of stocking stuffer items — very high margin products — that we largely did not sell the rest of the year. Basically, we offered good value on what people wanted during the holiday season without undercutting our value proposition for the rest of the year.

A customer who bought the exact train set or RC helicopter he or she wanted a few months before did not begrudge us selling specific models that we clearly purchased by the hundreds at lower prices. That protected our relationship with our regular customers and kept people from feeling the need to “wait for a deal” in order to get our best prices.

Amazon (and a very few other retailers) don’t need to do that. The online giant can undercut its own prices to capture more dollars knowing that consumers will still shop there and that, for some reason, those who paid full price a few weeks or days ago won’t feel betrayed (though they may think twice next year).

Basically, the big boys can say “I’m willing to sell a TV, a streaming device, or some other item to a person who needed one and would have paid full price so I can make sure more people who just want one for a holiday-related reason buy from me.”

Smaller retailers can’t sacrifice months of margin just to capture more sales. With the largest players doing exactly that, it’s very likely that the rich get richer this holiday season, and the growing retail divide between winners and losers continues.

How do you shop?

An elongated holiday season makes it impossible to know when the best deals are. That’s also good for the biggest retailers because, if a consumer makes a major purchase from Best Buy in October, he’s not likely going to notice or care if a desperate Sears discounts the same item to a lower price in mid-December.

In a three-month holiday season, it’s much harder for consumers to know when to buy. That actually might lead to more retailers selling items at really good, but not incredibly good deals. There may, of course, be some desperation pricing as Christmas draws closer, but are you really going to return an appliance or a sofa just because there’s a better deal?

The endless holiday season means that you should buy when an item becomes available at a price you feel comfortable paying. You can also monitor that same retailer — as many offer price matching if they lower prices over varying periods of time — but mostly, you should focus on getting good deals, not trying to get the best possible price when it’s something you actually need.

How does this impact long-term investors?

The companies that were strong heading into the winter should emerge as the winners after the holidays. These are largely the players with the most buying power, the most versatile supply chains, and the ability to roll with ever-changing demand in what has been a very strange year.

It’s also possible (it usually happens) that the holiday season will produce a surprise winner or two. The challenge there as an investor is determining the “why.” Did a struggling company do well because its bigger/more successful rival dropped the ball in some area? Or, did it succeed because it actually meets a need for customers that will continue past the holiday season?

Holiday creep only benefits a few retailers — mostly the ones doing well already. For the rest of the field, it can lead to either missing out on sales or over-discounting and having good comps but lousy margins or even losses. This should, however, provide investors some added data points as to whether some of the middling retail players — think Macy’s and Kohl’s — will stack up compared to the big boys.

Already a 7investing member? Log in here.