Google just released its annual When to Buy Guide, analyzing historical promotions, search trends and discount data across U.S. merchants to predict when holiday deals are likely to peak. The findings are compelling—but they also complicate our annual Black Friday cart sprint. Shoes, for example? Buy them over Black Friday weekend, when both selection and discounts are strongest. Fragrance? Shop within the two weeks afterward. Personalized gifts (read: and !) need securing early—as in now. As for designer bags, late December brings the deepest discounts on whatever remains. Emphasis on whatever is left. The Row just re-released its Idaho bag—and it’s already sold out. I ended up snapping up a very good on Amazon, below. This led to another useful discovery: is selling many of its bestsellers at up to 40% off right this minute—and only for the next three days! Apparently smarter holiday shopping requires both historical data and the occasional well-timed scroll. Some of my picks: the best-selling jacket, above, that my sister stole from me and needs to buy for herself (hint, hint!), ’s zipper-trimmed sweatshirt, ’s knee-high boots, plus galore.