Most people know me as an audiophile. That's great and all, but most people wouldn't know what to get an audiophile for the holidays. (Hint: Don't get Beats.)
But seriously though, if you have an audiophile in your family, or know someone who is an audiophile, here's a list of things they'll probably want, especially if they're just starting out.
The PM-3s are my go-to closed-back headphones. They're neutral but have a slight boost in the bass department. They can easily be driven by a phone's built-in headphone jack (or dongle, if you have the iPhone 7). But they will open up a bit more with proper amplification. They're also stylish as well, but that's not why an audiophile gets a set of headphones. They're admittedly pricy at the $400 price point but if you can find them for lower, these are personally my favorite set of closed-back headphones. They don't offer features such as noise cancelation but they seal well enough that you wouldn't need it in most cases. They come in black, white, and a blue color but retail for $400.
On the other end, the HD 600s are by far my favorite overall headphones. They're open-back meaning you probably shouldn't use them outside of your house unless you want everyone to hear the Taylor Swift you're listening to. Being open-back means sound will leak beyond your imagination but the trade off is worth it as a desk headphone. These things can technically be driven by your iPhone and do an adequate job but I would highly advise against it. An amp/dac combo is definitely required for this headphone. But once you drive them right, you'll finally understand what music is. They're priced at $300 brand new but I would get them used or refurbished for around the $200-250 range, there's a pretty good used market for these. Not the most stylish headphone, but sound trumps looks any day.
So now that you've got a great pair of headphones for your family member or friend, now it's time to talk about amps/dacs to drive them. For a mobile setup, I can't recommend the DragonFly series enough. The DragonFly Black does wonders for the aforementioned Oppo PM-3s. The DragonFly Red will drive harder headphones if need be. An important thing to understand about amps/dacs are the impedance (better known as ohms) rating. The lower the number, the easier they are to drive. For example, the EarPods are rated at 45 ohms which means they can be driven by pretty much any device. But something like the Sennheiser HD 600s have an impedance rating of 300 ohms which would require external amplification to drive them. The Oppo PM-3s have a 26 ohms rating, which means they can be driven from a mobile device such as a Google Pixel or an iPhone rather easily. The DragonFly Black should be able to drive most consumer-grade headphones, and the Red is really only needed for something more tougher to drive, like the HD 600s. The DragonFly Black retails for $100, while the DragonFly Red goes for $200.
As a bonus, you can pick up the Apple Lighting to Camera Kit adapter and plug that into your iPhone and use the DragonFly that way. A similar solution for microUSB phones is also available.
For a desktop setup, the OriGen+ is for those who are looking for a simple amp/dac setup. It has a volume knob and works strictly off of a single microUSB cable for both power and data. It offers both a 1/4-inch and 3.5mm port on the front and while you can use both of them at once, it's probably not a good idea as both headphones would likely need their own individual volumes. It also offers a 3.5mm port on the back if you'd want to amp your powered speakers. However, you'll need an external power source for the OriGen+ if you want to go that route. The Micca OriGen+ retails for $110 and for that price, is a must for any audiophile setup.
Runners-up
I realize that most people will only want easy to drive headphones that they want to power straight from their smartphone or laptop, so here are a few headphones I can recommend for that group of people.
First and foremost, the Audio-Technica MSR7. The MSR7 are similar to the PM-3s in the sense that they are fairly neutral headphones. Though, they do have a slightly recessed bass and a bit of emphasis on the treble, but not enough to drive you absolutely insane. You can't go wrong with either or. At $190, these are an absolute bargain for what you're getting. Though, there is a slightly more expensive version of the MSR7 with active noise cancelation if you’re into that.
The Philips SHP9500 are a pretty good set of easy to drive open-back headphones as well. They perform similarly to the HD600s with a tad more soundstage and bass, but for a fraction of the price. For $80, these are incredible.
