The first strategy is to segment your customers by their shopping behaviors. Do they tend to gravitate toward discounts, or are they frequent buyers of premium items? Group your customers into categories like “bargain hunters” or “luxury lovers” and create gift guides that reflect their preferences.

For example, a discount shopper may appreciate a guide focused on holiday sales or accessories, while high-end customers might prefer a selection of your premium products. This way, you’re creating a guide around their past behavior that is much more likely to result in a sale.

Another way to personalize your gift guides is by segmenting your customers by their favorite product collections. Group your customers based on the collections or categories they have shopped in the past, and send them a gift guide from the same category of products.

Let’s say a customer has purchased several products from your outerwear collection. You can create a holiday gift guide featuring more outerwear, or introduce them to a collection that pairs well with what they’ve already bought. This strategy helps you highlight what they love while offering fresh options.

The final segmentation strategy is to group customers by their specific purchases. You can use past purchases to recommend complementary products, similar styles, or the same product again if it’s an item that needs replaced more regularly.

For example, if someone recently bought a cozy sweater, you could send them a guide featuring scarves, boots, or jackets that pair well with it. This not only feels personal but also encourages add-on purchases that boost your sales.

Another way to send gift guides (without relying on specific segmentation) is just to ask customers what they're looking for. It may seem too simple, but directly asking what they’re shopping for feels personal and is likely to get a response. A quick message like, “Hey Ben, are you looking for anything specific this holiday season? I’d love to put together a personalized gift guide for you!” opens up a conversation that leads to meaningful engagement.

This approach is highly personal and makes the customer feel valued. Plus, once they tell you what they’re searching for or who they’re shopping for, you can quickly whip up a tailored guide that drives conversions.

Finally, if you want to keep things easy while still being personal, just send a guide of your favorite products. This utilizes the trust and expertise that you’ve built with your customers. It can be as simple as creating a guide called “Store Staff Picks” or “My Favorite Products.” Some brands personalize this further by having their associates send a picture of them wearing their top outfit followed by a gift guide with all the individual pieces.

This is best for customers who have shopped with you in-store before and will feel like they’re getting an inside look. By offering your expert recommendations, you create an authentic, personal touch that builds trust.