Look to Past Years’ Sales for Guidance - Retailers don’t exactly recycle Cyber Monday deals from year to year, largely because consumers are so fickle and product life cycles are too short. But you can reliably predict the types of products on which you’ll find the best deals. Electronics, clothing and apparel, and cosmetics are all Cyber Monday stalwarts. For more specific guidance on retailers’ wheelhouses, check out prior-year Cyber Monday flyers. Just Google the retailer’s name and “Cyber Monday [year] flyer.” Look for flyers on retailers’ official websites. Screenshotted flyers on shopping blogs and discount aggregators are more likely to have errors or inaccuracies, as retailers sometimes release multiple versions of flyers before Cyber Monday hits.
Bookmark Your Favorite Retailers’ Websites - Bookmark each useful retail website as you go. If you’re shopping for multiple people, you’ll probably accumulate a pretty long list of options. Create a separate Cyber Monday or “online shopping” folder to sequester your retailer bookmarks. For memory’s sake, I customize my bookmarks’ names with words or phrases reminding me why they’re useful – for instance, my Fry’s Electronics bookmark says, “PC accessories and home entertainment.”
Follow Your Favorite Retailers on Social Media - The best way to stay up-to-date on late-breaking retail promotions at any time of year is to follow your favorite retailers on social media. This strategy is especially fruitful during the holiday shopping season and just after, when clearance sales are common. (Fun fact: The best time of year to shop for a new TV is actually January, when retailers rush to offload their remaining stock of prior-year models that didn’t sell during the holidays.) Twitter is probably the best venue for information about time-limited deals and sales on specific products or product categories. I recommend creating a Twitter list specifically for the retailers you follow.
Sign Up for Retail Newsletters - This old-fashioned strategy is no less useful than following your favorite retailers’ social media profiles. It costs nothing and takes five seconds of your time to sign up for an email newsletter. Do it for every retailer you’re seriously considering patronizing this holiday season. Being a newsletter junkie has an obvious downside: lots of promotional emails, especially around the holidays. Your email client probably allows you to create a special folder to keep them sequestered, though, or uses an automatic filter anyway. Gmail shunts all emails deemed promotional into its Promo folder, keeping them out of your main inbox. Set aside a few minutes every couple of days to sort through your promotional emails en masse.
Make Your Holiday Gift List as Early as Possible - Use your social follows, newsletter memberships, and old-fashioned research skills to build your holiday gift list as early as possible. Rather than manually monitor websites for updates, you can use an app that automatically alerts you when a specific page’s content changes. App quality varies, and they’re sometimes harder to work with than they sound, so do your research before you select one. The best apps generally aren’t free, though they may follow freemium models that allow a limited number of alerts before the pricing structure kicks in.
Stock Up on Discounted Gift Cards - Don’t wait until the holiday shopping season kicks off to start stocking up on discounted gift cards. The best places to find cut-rate gift cards from your favorite retailers (rather than paying full price in the grocery store checkout line) are online clearinghouses like Raise and CardCash. Both stock physical gift cards and online coupon codes from hundreds of popular retailers, including some of the biggest names in the business. DealsPlus focuses more on online coupon codes, again for some of the biggest U.S. retailers around.
Research Shipping Policies and Fees - Many retailers offer free shipping on Cyber Monday, even if they don’t at other times of year – “free shipping on all orders” is a very powerful temporary selling point. Unless you’re shopping for products that aren’t available on free-shipping sites, I’d recommend avoiding retailers that charge for shipping on most or all orders. If your preferred retailer offers free shipping on orders above a certain size, determine whether it’s feasible to spend that much (meaning, whether you would have spent that much anyway) before you place your order.
Research Return Policies and Fees - Before you buy, look into retailers’ return policies and fees. Most clearly state their return policies on their websites, but it’s worth calling customer support if there’s any confusion at all. Return shipping charges and restocking fees really eat into refunds or store credits, leaving less left over to rectify the mistake and fund the rest of your holiday shopping. They also distort consumers’ decision-making processes. I recently purchased several pairs of bike shorts from a New York State bike shop’s online store in preparation for a long-distance bike ride. Two pairs were a size too large; I saw chafing and discomfort in my future. I looked up the shop’s return policy for online sales and, lo and behold, I’d be responsible for return shipping charges – just under half the total cost of each pair. I decided the added expense wasn’t worth it and held onto the shorts.
Set a Firm Budget - The first rule of Cyber Monday shopping is simple: Stick to your budget. Figuring out how that budget should look in the first place is another matter. The L.A. Times offers some general guidelines on holiday spending: $20 and up for siblings and cousins, $25 and up for nieces and nephews, $20 and up for parents and in-laws. But there’s obviously a big difference between spending $25 on a nice new tableware set for your mother-in-law and shelling out $200 (or more) for a new table. Your broader financial picture plays a crucial role too. As the Times itself notes, paraphrasing consumer spending blogger Leah Ingram, “A surgeon earning six figures will have a different budget than an elementary school teacher.”
Use a Price Comparison Tool - Don’t pull the trigger on a Cyber Monday purchase until you’re (reasonably) sure you’re getting the best possible deal. Use a price comparison app or toolbar (if you’re shopping on a desktop) to see which retailers are offering the lowest prices on the big shopping day. Shopify has a good roundup of legitimate price comparison apps, including some free options. (The article is written for merchants, but the same rules apply to shoppers.) One of the best-regarded is PriceGrabber.
Create a Spreadsheet With Sale Information and Links - If you’re a “spreadsheet person,” this is an evergreen strategy that can save you serious money on online shopping throughout the year. Create a spreadsheet with site descriptions, links to interesting products (or examples thereof), price ranges and comparisons with competing retailers, discounts and promotions (including Cyber Monday sales), shipping policies, and other pertinent information. Update it whenever you come across a new retail website. In no time, you’ll have an encyclopedic resource customized to your online shopping preferences (and your holiday gift recipients’).
Avoid Sites With Poor Security Practices - Don’t gamble with your identity. Stay away from retail sites with lackadaisical security practices. Two key practices stand out in particular: SSL certificates and Verisign domain protection. SSL is an encryption protocol that renders it much more difficult (though not impossible) for bad actors to steal payment card information and other personal data during the payment process. Look for “https” at the beginning of the site’s URL. You should never enter payment card information on non-“https” pages, period. If you’re shopping on a mobile device, download your favorite retailers’ verified apps too. Apps downloaded from a legitimate source, such as the Google Play Store, are much less likely to be compromised.
Rise Early or Stay Up Late the Night Before - Most retailers run Cyber Monday sales for at least 24 hours. Many begin them before Cyber Monday itself, or fold them into longer “cyber weeks” or Black Friday weekend sales. If you’re shopping for common products for which demand is measured, you probably don’t have to get up at (or stay up until) 1am to snag the best deals. However, if you’re worried about items running out of stock – a common problem on the weekend after Thanksgiving – then you’ll want to shop as early as practically possible.
Shop in Incognito or Private Mode - Do your actual shopping anonymously(ish) using your browser’s private or incognito mode. This isn’t a foolproof way to mask your identity to retailers, but it can render you eligible for deals not available to someone with your browsing or purchasing history. (Yes, retailers know way more about you than you realize.) Using your browser’s private mode reduces your exposure when you shop at inappropriate times – like, ahem, at work. Even if it doesn’t directly save you money, avoiding your boss’s ire (and potential disciplinary consequences) is obviously a good thing in the long-term.
Use a Rewards Credit Card - The right rewards credit card can significantly reduce the cost of your holiday shopping campaign. I usually recommend flat-rate cash back credit cards, such as Barclaycard CashForward World Mastercard (unlimited 1.5% cash back) or Citi Double Cash Card (unlimited 2% cash back). In this instance, though, cards with rotating rewards categories really shine. Every quarter, Chase Freedom and Discover it pay 5% cash back on up to $1,500 in net purchases in one or two rotating categories – up to $75 in bonus cash back per quarter. Department stores routinely appear in the mix, and the category is broad enough to encompass many of Cyber Monday’s most popular retailers.
Monitor Your Bank Accounts, Credit Cards, and Credit Profile for Suspicious Activity - The holiday shopping season is the busiest time of year for credit card fraudsters and identity thieves. If you avoid sites with poor security practices and keep your eyes peeled for potential scams, you’ll reduce your likelihood of victimization, but it’s impossible to cut your chances down to zero. As long as you shop online, the risk is there.