Jeremy’s 2019 Apple holiday shopping guide

As the holiday shopping season is officially kicking off this week with major deals across the United States, it’s time to sort this year’s best Apple gifts from some of the company’s less-than-ideal alternatives. That’s where I come in.

Apple released quite a few great products over the past year, and there are already some hot deals on both new 2019 and discontinued 2018 options. My goal isn’t to point you in the direction of specific discounts, but rather to help you focus on what your lucky gift recipients will enjoy the most — with the fewest problems.

Here are my holiday 2019 suggestions, sorted by major Apple product line. I’ll also note items that I’d suggest skipping this year, though some of them may be worth considering anyway if you come across a particularly excellent deal.

My top pick: AirPods

Building on the strength of its original AirPods — completely wireless earphones — Apple released two new AirPods models in 2019: second-generation AirPods ($159) with the option of a Qi wireless charging case ($199), and AirPods Pro canalphones ($249) with a Qi wireless charging case included. Each AirPods bundle includes four pieces: left and right earphones, a charging case, and a Lightning charging cable.

I’m a big fan of AirPods in general, but my buying advice here is a little nuanced. If you have the cash for the Pro model, just do it. They sound better, fit better, and have active noise cancellation that the standard AirPods lack. I love my Pros, and since I plan to use them quite a bit, Apple’s optional $29 AppleCare+ warranty package for headphones struck me as an all but mandatory addition to the package.

That said, my family members love their hand-me-down standard first- and second-generation AirPods; I would recommend them to anyone who doesn’t want to spend the extra money on the Pros. You’ll be just fine picking the $159 model unless your gift recipient already has or plans to buy a Qi wireless charging pad.

Solid options: Apple Watches + accessories

There’s good and bad news if you’re considering buying an Apple Watch right now. Good: The two-year-old Apple Watch Series 3 is now being offered for the lowest prices ever, starting at $199 for the 38mm GPS model, with sales occasionally pushing the GPS + Cellular version down to that price. Walmart (and possibly Apple) will be selling this model for as little as $129 on Black Friday, which is a remarkable — arguably must-grab — deal.

My personal feeling is that this is the best time in history to purchase a non-flagship Apple Watch, regardless of the model you choose. With Series 3, you get features such as a respectably fast Apple S3 processor, true waterproofing, and barometric altimeter for the price.

The bad news is that Apple Watch Series 5 isn’t much of a step up from the great Series 4 model it replaced this September. Series 5 has an always-on screen that drains battery life, and an iffy compass, but not much else to set it apart. While you can buy it, my advice is to pay less for a discontinued Series 4 model instead and get 95% of the performance at a nice price savings. Best Buy is offering Series 4 on Black Friday for $299 (aluminum/GPS) or $399 (steel/GPS plus cellular), which gives you access to a bigger screen than Series 3, EKG functionality, and a faster processor.

If your gift recipient already has an Apple Watch, an official Apple Milanese Loop band in silver, black, or gold would be a superb accessory. The Loop has dropped in price to only $99, and it makes it incredibly easy to get the Watch on and off your hand. Although you can find knock-offs cheaper on Amazon, every one I’ve tested has developed issues during its first six months of use, while Apple’s have lasted years without problems.

iPhones + Accessories

If you don’t care about the next-generation cellular network technology 5G, which is already rolling out in the United States, Europe, and China, Apple’s latest iPhone 11 models are great. For most people, the $699 to $749 iPhone 11 models with 64 or 128GB of RAM (and twin cameras) are more than enough phone for now, so only consider the $999 and up iPhone 11 Pro with triple cameras if you really need a 2X rear zoom lens. They’re all nice devices, but not major steps up from the iPhone XR and XS models they replaced.

Apple is well established to be working on 5G phones for 2020 — most likely both midrange and high-end models called the iPhone 12 and iPhone 12 Pro — so I generally would not advise the purchase of a new iPhone right now. Holding off until September 2020’s release of the first 5G iPhones will result in tremendous cellular performance gains, as well as complete redesigns with screen, camera, and A-series chip improvements. So if you must upgrade this year, consider putting less cash into a discontinued iPhone X, XR, or XS you can trade in next year; carriers and shops are offering nice deals on these 2017-2018 phones.

This year, there are two categories of iPhone accessories that I’d recommend that you consider as long-term investments. First up are Qi wireless charging pads, which have really come into their own over the past year or so. Thanks in part to Apple’s decision to announce and then abandon its own AirPower multi-device charger, a company called Betafresh released a similar-looking but simpler option called AirUnleashed. The vinyl-covered pad is designed to simultaneously charge the iPhone, Apple Watch, and AirPods (in that order) in one straight line, fueling all with a (too short) power cord and included wall charger. Normally, AirUnleashed is sold only in white, but this black version will be available starting on Black Friday.

Though it’s $40 more expensive, I’d lean towards Mophie’s 3-in-1 Wireless Charger, which has a more Apple Watch band-friendly charging puck, and more room for the AirPods and iPhone, though centering the phone can be a hassle. I haven’t seen any Black Friday deals on this unit yet. If you can choose between the glossy plastic or fabric versions, I’d suggest the latter.

While multi-device chargers strike me as the best option, Totallee is selling single-device chargers at lower prices. It recently released a motorized Qi charger built into a car vent mount, using sensors to automatically clamp your phone and begin charging. It also offers a handsome fabric and metal single-device pad that you can use to alternate charging between supported devices. Each sells for $59, and the company is offering 10% off through its website.

The other big category is camera accessories. Apple has spent the past few years really enhancing iPhone cameras to compete with point-and-shoot cameras, such that iPhone X, XS, XR, and 11 series devices all can capture great-looking photos and videos. But they can’t do everything on their own, which is why companies such as Moment have developed camera add-ons that go further, adding more zoom capability ($120), cinematic optics ($150), and polarizing filters ($40-$50) that can remove shadows and glare from glass and water, making them look clear.

I’m highly impressed by everything I’ve tested from Moment, and that’s not something I say lightly. The build and optical quality of the lenses and filters are the best I’ve yet seen in any smartphone accessories, comparable to add-on lenses offered by major camera vendors for point-and-shoots. Each metal-bodied lens ships with a rubber lens cap and carrying case. The lenses and filters are device-agnostic, attaching to cases that are custom-fit to each iPhone.

Versions for prior iPhones are available now, with iPhone 11 and Pro versions arriving in early December. I was able to test one of the iPhone 11 Pro cases early, and it’s a case I would use on my personal iPhone every single day — something I’ve generally hesitated to say in the past about lens adapter accessories for iPhones. That said, iPhone 11 users will likely need to use Moment’s $6 Pro Camera app to take full advantage of the lenses, rather than Apple’s own Camera app; additionally, Moment supports only 1X and 2X lenses, not the 11’s ultra-wide-angle lens.

If you’re really into shooting cinematic video, DJI recently released the $119 Osmo Mobile 3, a battery-powered gimbal that lets you smoothly track subjects with and rotate your device while moving around. The standard version is purely handheld, folding down into a tiny size for carrying, while a $20 tripod accessory (sold in a $139 combo pack) lets you place the gimbal on a stationary mount as needed. Amazon is already offering $10 off on each version, and DJI will offer a similar promo in December.

Apple TV: Probably pass this year

Apple currently sells three versions of its standalone Apple TV media player, starting at $149 for a 1080p version (Apple TV HD), and $179 to $199 for 4K versions (Apple TV 4K) with 32GB or 64GB of storage. For the time being, I wouldn’t recommend buying any of them. Put the same dollars towards a smart 4K TV, instead.

Up until this year, only Apple devices could play back movies and TV shows purchased or rented from iTunes. That changed after Apple expanded direct iTunes video streaming support to free apps for Samsung smart TVs, Roku TVs and players, and Amazon Fire TV devices, with AirPlay 2 streaming support for other televisions. Since tvOS-specific apps and games for the Apple TV have been a bust, hold off on buying an Apple TV until Apple shows what it has in store for 2020 — a new model is expected to debut in the first half of the year.

Mixed bag: iPads + Accessories

2019 was a pretty big year for iPads: Apple replaced the entry-level $329 9.7-inch iPad with an otherwise unchanged 10.2-inch model, updated the $399 iPad mini to a faster and Apple Pencil-compatible fifth-generation model, and re-introduced the iPad Air as a $499 option with a 10.5-inch screen. On the high end, it left last year’s 11- and 12.9-inch iPad Pros untouched, still with $799 and $999 entry price tags.

If I was buying an iPad today, I’d lean towards either the iPad mini 5 or iPad Air 3, depending on the screen size you need. I still love the mini’s form factor and 7.9-inch screen size, but if you’re using a Plus- or Max-sized iPhone, there’s not enough difference to justify having both devices. So if you’re an adult with no need to use the device for work, go with the iPad Air instead. For kids, go with the entry-level iPad or mini 5, depending on the physical size you prefer.

The only reason I would hold off on buying an iPad Pro right now is that new models are coming in 2020. My 11-inch iPad Pro is unquestionably the best iPad I’ve ever owned in every regard — fast, with a beautiful screen, and fairly long-lasting in the battery department — but the price tag remains high, and it’s a year behind in both chips and cameras compared with the latest iPhones. Consider a Pro if you can get a nice enough deal to avoid feeling jealous when next year’s model comes out; otherwise hold off and see what Apple does in 2020. (For Black Friday, Amazon is offering $125 off the normally $799 base Pro model with 64GB, and there may be better deals.)

The coolest iPad accessory I’ve seen all year is Kanex’s 6-in-1 Multiport Docking Station, which adds SD and microSD card slots, 4K HDMI, USB 3.0, and 3.5mm headphone ports to the latest iPad Pros in a single iPad-matching housing. Since it can also be used with USB-C laptops, it’s now a must-carry item for iPad and MacBook users. Kanex is offering 10% off its $100 MSRP for first-time customers.

Macs + Accessories

This hasn’t been either a great or especially bad year for Apple’s Mac computer lineup, which used to see regular yearly updates but has more recently settled into 1.5 year or longer cycles. As laptop and desktop computers don’t change form factors or major components as often as phones and tablets, it isn’t critical to buy the very latest Mac, but it’s hard to recommend investing $1,000 or more in something that’s about to be discontinued.

To that end, the long-in-the-tooth Mac Pro is finally getting both a complete redesign and new XDR Pro Display monitor in December, even if most people wouldn’t think of spending over $10,000 to buy them. Then there’s the just-released 16-inch MacBook Pro, which seems comparatively affordable at only $2,400, and finally has a properly designed laptop keyboard. If you’re able to get or give one of these as a holiday gift, consider yourself lucky indeed.

The rest of the Mac lineup hasn’t changed much over the past year, and I’d expect most of the models to see non-trivial upgrades in 2020. Apple’s top-selling 13-inch laptops, the MacBook Pro and MacBook Air, are currently both saddled with keyboards that have serious reliability problems. Improved “Magic Keyboards” are likely to come to both models in 2020, but Apple promises to fix current and earlier machines for free when they fail, if you want to take the risk. (My own MacBook Pro keyboard has failed twice now, so it’s not an abstract concern as far as I’m concerned.)

Apple gave the iMac only a small bump in early 2019 ahead of an expected major redesign in 2020. Apart from the risk of replacement, it’s otherwise a great overall machine, as is the Mac mini, which stayed the same throughout 2019. It’s unclear whether the iMac Pro will remain in Apple’s lineup after the Mac Pro hits shelves this year.

I’d originally planned to purchase either a new iMac or Apple monitor this year, but decided to hold off. Instead, I bought an LG 27UK850-W 4K HDR display for my laptop, scoring a 27-inch screen with (small) internal speakers, USB-C connectivity, and USB-A ports for around $400. It’s a step below all-in-one Apple display perfection but offers great performance for the price, and it provides a one-cable connectivity and charging solution for my current 13-inch MacBook Pro. It’s the best Mac accessory I’ve tested all year.

HomePod: Once again, probably skip it

Last year, I named Apple’s “smart speaker” HomePod as Apple’s holiday lump of coal and strongly advised users to “just say no” to purchasing it. Since then, HomePod sales apparently flatlined, leading Apple to uncharacteristically drop its price. And though the company recently updated its software with new features, it’s still a mess.

If you’re not familiar with HomePod, it’s a small, barrel-shaped speaker that uses AirPlay 2 to stream audio wirelessly from Apple devices and iTunes-equipped PCs. It’s not capable of actual stereo sound unless you buy and pair two units, but each unit has solid bass performance and can be turned up quite loud. Almost everything is controlled by a Siri voice command system, which is … well, Siri, so you’re best off not expecting too much and occasionally being pleasantly surprised.

I still wouldn’t recommend HomePod to most users, but Best Buy is offering it for $199 — a less terrible purchase than it was at its original $349 and $299 MSRPs. If you’re in the market for an all-in-one speaker, and comfortable waiting on Apple to fix its non-trivial remaining bugs, $199 is at least closer to right-priced than it was before.

Stocking stuffers

Looking to spend less money on Apple-related gifts? Here are a few other items to look out for over the next few weeks.

• Discounted iTunes gift cards. If you can get them for 15% off, that’s a nice savings on the cost of videos, Apple Music, or Apple TV Channels subscriptions you might be considering. Costco is currently offering $15 off a $100 card through December 2.
• A new iPhone or iPad case. I personally do all my case shopping for myself and my family through Amazon, focusing on Spigen iPhone cases and “fun” but highly-rated iPad cases for the kids. But after my positive experiences with Moment’s camera accessories, I’d suggest considering one of their Filmmaker Cases, if you enjoy iPhone photography.
• A PlayStation 4 DualShock 4 controller. Now compatible with everything from Apple TVs and iPhones to iPads and Macs, these rechargeable Bluetooth controllers are often on sale for $40 during the holidays, and are exceptionally well-made.

Regardless of the holidays you celebrate, I hope you and yours have a wonderful time giving, receiving, and using these gifts!