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How to Win Cyber Monday With The Best Deals And Discounts in 2021

Trae Bodge  |  November 25, 2021

The sales, bargains and shopping strategies you need to know about for 2021 Black Friday, Cyber Monday and into December.

Ready to shop for the best sales and discounts during Black Friday and Cyber Monday? Whether you’re looking to update your own wardrobe (following a very long sweat-pants heavy pandemic ) or you’re looking to gift the people you love with some incredible holiday finds, we’ve got a rundown on exactly what you should be shopping for in 2021 to score the best possible deals and bargains.

What categories should we focus on over Black Friday and on Cyber Monday?

You’ll be able to find deals across all categories, but the categories to really watch are tech, like laptops and tablets, small home appliances, like robotic vacuums, and beauty & fall apparel/footwear. Because of potential supply chain issues, I would also look for deals on any specific items you happen to have on your holiday gift list.

What offers are you most excited about?

If you’ve hesitated to spring for those pricey Airpods, as I have, now is your chance to save on them. The Apple Store doesn’t tend to offer very exciting discounts around this time, but sometimes other retailers will.  Amazon is planning to offer $50 off Airpods Pro, which is a nice deal, but visit other retailers that carry Airpods, like Best Buy, Target, and Walmart to compare sale prices.  You’ll find great deals on other phone accessories as well.

Small home appliances are also a hot category, so you’re curious about air frying, multi-use cooking appliances, like the Instapot, or hands-free vacuuming, now is your chance. For example, I love the robotic vacuum that I bought on Cyber Monday a couple of years ago, and Amazon will be offering $100 off the iRobot Roomba this year.

Okay. Let’s get real about Cyber Monday.  What do we need to know?

Cyber Monday is a great day for broad discounts – both category-wide or even site-wide. Retailers also often offer slightly deeper discounts on Cyber Monday, so if you hesitated to get something on Black Friday, check again – you might find a better deal!

But if you are looking for travel deals, wait for Tuesday. According to data of over 25B flight and hotel prices from the travel site, Hopper, Travel Tuesday has consistently been the best day in the post-Thanksgiving shopping period for travel deals with 30 percent more deals than the average day.

What about in December, after all the shopping holidays are over – what will be on sale?

Historically, winter apparel, toys, and holiday-themed merchandise and gift sets are better-priced in December especially on the following days: Green Monday (Dec. 13), Free Shipping Day (Dec. 14), and Super Saturday (Dec. 18). But keep in mind that you won’t see as many discounts good as what will be on offer for Black Friday or Cyber Monday, but it’s worth looking!

This November is supposed to be a good time for apparel deals… Any favorites?

You’ll find deep discounts at lots of popular sites – I would look for discounts in the 25-40% off range. For example, Target is offering 30% off sweaters and cold-weather accessories (which is exciting because cold weather apparel is usually more deeply discounted in Dec. but don’t forget to check deal sites for additional ways to save., which is a real-time coupon code search engine and directory will have lots of exclusive deals, including 20 percent off TipsyElves holiday-themed merchandise with code CF20OFF, and 15 percent off apparel brand Missguided with code NEXTGEN. They also have a very helpful browser extension called Cently, which will automatically alert you to savings as you browse online.

What are some surprising ways to save?

We will need to try a bit harder to save in December, so pay attention to what retailers are offering, but you can often sweeten any sale by checking deal sites to see what they’re doing. For instance, CouponCabin, which is already great for cash-back offers, has a new 5X Cash Back page, where 20 stores each day will be offering 5X their regular Cash Back for a few days at a time. I would also look at exclusive discounts that your credit card is offering and, if you’re into the new Live Shopping Trend on platforms like Facebook and Instagram, there will be exclusive offers during Live Streams.

How do we avoid stress and save money as we work through our shopping lists?

If you have lots of gifts to buy, consider signing up for SmartyPlus, from deal site Smarty. It functions like a shopping assistant, getting you double cash-back and access to exclusive sales, plus it helps you compare prices, get credits for price drops and rebates for shipping & return costs, and it has travel perks, like car rental protection and rebates for air-travel purchases. They also just added food delivery rebates of up to $15 a month. If you have food delivered regularly, this benefit alone almost covers the monthly cost of the membership.  SmartyPlus is $19 per month and you get $15 cash-back for signing up.


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