Consider this your Holiday planning guide. If you are in the retail industry we will have fun getting into the weeds together — fashion nerds unite! If you are an influencer, creator, stylist, or personal shopper you can use this to help guide your work. And aren’t we all shoppers? For those that are shopping I’m bringing you into the stockroom to explain why we retailers think the way we do. Sure, some things should change (okay, fine, many things…) and there is always a case of last-year-itis but this helps explain where we get these retail quirks from.

Useful tip for retail industry insiders: did you know you can purchase a group package for Private Label? I’ve already seen some of the smartest, most innovative retailers purchasing for their teams. Three or more subscriptions get you 20 percent off. Use this template to request expensing your subscription at work.

What Merchants Already Know About Holiday 2026

Halloween is next weekend but the Q4 plans have been locked and loaded since July. At least. As soon as Holiday 2025 ended, retros (a critical look back at the season) kicked off. I’ve had CEOs, executives, founders and retail analysts messaging me asking what I’ve been seeing. Here is what I’ve noticed during Channel Checks:

Christmas and Hanukkah decorations are already up. In some stores it feels like we skipped Halloween and fall and moved right to the main event — Thanksgiving through Christmas.
Saks has had their Christmas trees and decor up for the past few weeks (at least at the 5th Avenue location where I spotted them). Paper Source has Hanukkah decorations front and center. I’ve seen plenty of Holiday jammies (see here, here and here).
And retailer gift guides are in the website navigation. See J.Crew, Free People, Bloomingdale’s, Mytheresa and Moda Operandi as a few early birds. See below for an example of how adding the star icons to either side of “Gifts” and using a different color helps it to stand out.1

Private Label PSA

To keep everything organized this holiday season I’ll use this as Holiday Gift Guide central location (Gift Guides 2026). As the season progresses I will highlight Gift Guides and Trackers here. Currently we have:

More to come! Any special requests?

Calendar Planning

2026 holiday calendar with Black Friday, Cyber Monday, Hanukkah, Super Saturday, Christmas and New Year’s Eve circled

If you think (U.S.) Thanksgiving is always the last Thursday of November, and Christmas is always on the 25th of December, and New Year’s Eve is always December 31st and that’s the calendar, you would actually be wrong because the nuance is more than that. Sorry. Every year the calendar moves around — where the weekend falls in relation to Christmas, exactly how many days fall between Thanksgiving and Christmas, and how many weekends there are to shop.

Every year there are some quirks you need to highlight. Let’s look at 2026. Christmas and New Year’s Day both fall on a Friday. Cyber Monday is back in November. Hanukkah starts the first week of December (thankfully for my planning, it doesn’t fall in November like it did in 2021 and we are safe from that again until 2032). And the 2026 calendar is a match to one year no merchant can use as a comparison (more on that below).

Let’s walk through the calendar the way a merchant would and then you can also translate it for your own holiday shopping. This is the cheat sheet you should save and reference back to all season. One of my goals with Private Label is that retailers should understand customers better and customers should understand retailers better. I want us to all be on the same (digital) page.

The quick math: Thanksgiving is Thursday, November 26. That gives us 29 days from Thanksgiving to Christmas, just one more day than last year, with the same four Saturdays in between. This isn’t a “shortened Holiday season” year like 2024 but we’ve still got nuance.

Let’s look closer at the last few years:

How the Retail Calendar stacks up 2021 to 2026

In 2024 Thanksgiving fell on the latest possible date and we had five fewer selling days than 2023. An adjustment like that is something that retailers need to plan to make up in some form. Depending on revenue performance this is one reason we have seen Black Friday promos starting earlier. This year is pretty similar to 2025 in length. But every date shifted by a day, and that one day moves Cyber Monday back into November and Christmas onto a Friday. Another quirk to 2026, while it isn’t a Presidential election year, the mid-term elections with political ads and so much uncertainty around possible control of Congress adds event more complexity.2

The 2026 Dates Worth Noting

Sat, Oct 31: Halloween. The Holiday floor set is already done at most stores.
Tue, Nov 3: Election Day (midterms) Have you mailed your ballot or made a plan?
Wed, Nov 11: Veterans Day, a popular “Pre Black Friday” sale date
Thu, Nov 26: Thanksgiving
Fri, Nov 27: Black Friday
Sat, Nov 28: Small Business Saturday
Mon, Nov 30: Cyber Monday
Tue, Dec 1: Giving Tuesday
Fri, Dec 4 to Sat, Dec 12: Hanukkah (begins at sundown on the 4th)
Sat, Dec 19: Super Saturday, the last Saturday before Christmas
Thu, Dec 24: Christmas Eve
Fri, Dec 25: Christmas
Sat, Dec 26: Kwanzaa begins and the post-Christmas weekend kicks off
Thu, Dec 31: New Year’s Eve
Fri, Jan 1: New Year’s Day

What Merchants Know (and Are Planning Around)

Behind the paywall:

My shopping tips for this holiday season — from someone with 25 years of experience in retail
Hanukkah markdown timing and my personal shopping strategy
The year 2026 mirrors, and why no retailer can use it as a comparison
Retail nerding out with the 4-5-4 calendar (and why Cyber Monday throws off the monthly numbers)

Retail 101: The 2026 Holiday Calendar

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