Issue #163: Christmas shopping with a PSL in hand

It’s fall! Time for leaf peeping, spooky Twitter names, Halloweentown, dark lipstick, pumpkin cream cold brew, listening to “All Too Well (10-Minute Version) (Taylor's Version)” on repeat and, yes, eating candy corn every single chance I get.

I love October for many reasons, not least of which is that it kicks off the holiday season. The holidays are fun because every year, I spend weeks shopping for my family and friends. I’m on a mission to find the best — and, in most cases, dumbest — Christmas gifts I possibly can. It’s a lengthy process… and one that’s thoroughly enjoyable.

In fact, I’m so excited that I want to start my shopping now, even though we’re barely out of September. But I don’t know if my enthusiasm is going to end up biting me in the butt. What if, by jumping the gun, I’m missing out on sales that happen later in the year? I can’t risk that with inflation the way it is.

Let’s ask the experts. Is it too early to start my holiday shopping?

According to Julie Ramhold, consumer analyst with DealNews, no.

“It’s never too early,” she tells me. “If you find a good deal in April and you know it’s something you want to give to someone, why not? If it’s in your budget and you have a place to store it, go ahead and get it.”

That’s especially true now thanks to Christmas creep, a trend that’s emerged in the past few decades in which retailers start setting out their holiday items — and rolling out their holiday sales — as early as Oct. 1.

I don’t have to look any further than Amazon for proof of this: The company just announced another Prime Day for Oct. 11 and 12. Target, on the other hand, is holding its Deal Days this Thursday through Saturday.

“Retailers have seen that people are willing to shop for the holidays in October,” Ramhold says. “By stretching the season out, they're encouraging people to spend more.”

Black Friday be damned, I guess. A recent survey from the National Retail Federation found that 44% of holiday shoppers aim to buy gifts now because they believe inflation will drive up prices later on.

There’s a legit financial reason to begin my shopping in October, too: “It allows you to manage your cash flow and spread out those purchases,” says consumer savings expert Andrea Woroch. “If you plan to save and you don’t, come December you’re trying to buy all those gifts at once. You only have a couple of paychecks left, you go into debt and interest starts piling up.”

The only pitfall? By starting early, I may end up shopping more. Unless I’m smart about it, that is.

Ramhold says I should do some research ahead of time, putting together a rough list of presents I’m sure I want to buy and taking note of what they generally cost. That way, “when those deals do start popping up, you can know, ‘oh, that’s definitely a good deal’” and not worry about missing out, she says.

For Amazon, the price tracker camelcamelcamel provides historical price data. Woroch likes the browser extension Droplist, which alerts me when the price of something drops below a certain amount, and Santa’s Bag, which helps me budget and keep track of what I’ve bought.

Another trick for shopping early is to patronize retailers with price match guarantees. Target, for example, has a policy that if I buy something in store or online between Thursday and Dec. 24, 2022, I can request a price match. Last year, Best Buy had a price guarantee during its October sales in which it promised prices wouldn’t go lower before Black Friday.

It’s important to read the fine print on these policies, but they can provide some peace of mind.

“If a store is telling you ‘this is the lowest [price] it’s going to be,’ you can usually trust that,” Ramhold says.

I should also be strategic about what I buy when. Ramhold says that October is a good month to buy leftover summer items like grills, patio furniture and camping gear, but I’ll likely want to wait until Black Friday to purchase sweaters and boots because the deals will be better. Ditto electronics — with the exception of Amazon-branded products like Kindles and Fire TV devices, which will probably be at their cheapest on Prime Day 2.0.

Woroch says to buy hot holiday toys as soon as I see them in stores because they’ll probably run out, but if I’m flexible, I can wait until early December for deeper discounts. Postponing gift card purchases until right before the holidays is smart, too.

It’s all about being diligent.

“Retailers know that people are feeling the pinch with inflation, and they know people are planning to start early,” Woroch adds. “They’re going to be offering sales to get you to buy with them.”