Best headphone deals ahead of Black Friday, sourced by an expert tester

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I pretty much spend every day I'm at work testing out headphones and earbuds, which means I've become relatively well-versed in which headphones are actually worth your money.

This year has been an especially noteworthy year for headphones, with flagship releases from Sony, Bose, and Bowers & Wilkins. Flagship headphones are often the ones that get recommended on best of lists — ours included — but considering the new norm for a starting price is $449, they're not exactly the most affordable choice out there. Enter: early Black Friday deals, when tech deals abound.

As of Nov. 19, I've spotted five especially noteworthy headphones and earbuds on sale — all of which Mashable has recommended in some capacity. As we approach Black Friday proper on Nov. 27, and the start of Amazon's Black Friday sale on Nov. 20, I expect more deals to go on sale. But for the time being, here are the best headphones and earbuds deals ahead of Black Friday.

One of the most comfortable pairs of noise-cancelling headphones

The first time I put the Bose QuietComfort Ultra headphones on, I knew they were the most comfortable headphones I'd ever worn (Mashable's Sam Mangino had a similar experience). That belief became even firmer over years of use (and testing them against new competitors). Although the new second-generation headphones feel ever so slightly more comfortable, the originals still hold up.

On sale for $298, they're a much better value than the $449 second-gen Ultras. Their main quirks include no passive playback and the occasional difficulty pairing to more than one device. However, when I compared them directly against their newer counterpart, I found the ANC and sound to be very similar, making it easy to recommend grabbing these over the second gens if they happen to go on sale.

Sony headphones that sound incredible

The thing about Sony flagship headphones is that they're going to sound incredible. With the release of the XM6s, the WH-1000XM5 headphones are the former flagship headphones, but their sound profile remains one of the best in the game. I particularly like the "find your equalizer" feature that guides the less audiophile inclined among us through the process of finding their perfect custom EQ sound, which really helps these headphones shine. More generally speaking, when I tested the XM6s and XM5s head-to-head, I didn't find any huge discrepancies in performance. Plus, the XM6s got a $50 price bump to their list price, meaning that even if they were to get a $50 price drop over Black Friday (a markdown we've only spotted once before), they'll still be $150 more than the XM5s at this price point.

Mid-range headphones for under $100

Noise-cancelling headphones with great sound quality from a reputable brand don't need to cost several hundred dollars, and the Sony WH-CH720N are proof of exactly that. Mashable named them Sony's best headphones under $100, with Mashable contributor Alex Bracetti singing their praises after two years of use. He deemed their sound quality "near flagship" level, and was impressed by the 35 hours of battery life with ANC on, which beats out the current flagship models of both Bose and Sony.

Though you can often find them on sale for $98 (a feat on its own, considering their $179.99 list price), it's slightly less common to find them on sale for $89.99, making this a great deal ahead of Black Friday. As an added bonus, the pink colorway is more unique than you might find from other budget headphones options under $100.

The best sounding open earbuds

Open earbuds are great if you prefer staying somewhat aware of the world around you, but in my experience, that can come in the form of less-than-stellar sound quality. In the case of the Bose Ultra Open earbuds, you get the best of both worlds. I suspect that's a large part of the reason behind their $299 price tag (which feels more appropriate for noise-cancelling earbuds). That's why I recommend them as an upgrade pick for open earbuds, and why I'm an especially big fan of this $100 off deal. In addition to their surprisingly rich sound, I especially like their small charging case, smartly placed on-ear controls, comfortable clip-on design, and many options for colorways.

Excellent mid-range noise-cancelling earbuds

Rounding out my picks is maybe the most underrated Bose product — the QuietComfort earbuds. Though their design isn't the most elegant, that's pretty much where their underwhelming features end. For starters, these earbuds have incredible battery life — in my weeks of testing them, I rarely had to charge them, and easily squeezed in a five-hour day of use, with ANC on and battery life to spare.

Sound and noise-cancellation-wise, they don't wow quite as much as the QC Ultra earbuds, but they're also significantly cheaper, even at full price. For their $129 sale price, they're less than half the price of the premium earbuds, and I promise, their performance doesn't reflect that. If I had to put a number to it, I'd say there's more of a $50 to $75 performance discrepancy between the two earbuds, which is why we've named these the best mid-budget earbuds currently on the market. Though we've seen them drop to $129 before, it is their lowest price ever, making this a great grab ahead of Black Friday.