Related: Best Cheap Earbuds for Small Ear Canals: What Survived My Ears
I held onto a 3.5mm jack for years, and I still think wired sounds better. That opinion has not changed. What changed is that the adapters kept dying on me, one after another, until I had a drawer full of dead dongles and a phone that stopped cooperating. So I made peace with wireless, went down the review rabbit hole like everybody else, and came out the other side with a short list of budget headphones and earbuds I actually trust.
Here is the context that matters. I do live sound and recording cleanup work around Nashville, and at the desk I run a serious reference pair that never leaves the house. Everything else in my life runs on cheap gear: walks, chores, the gym, phone calls, the grocery store. That gear has to survive being lost, sat on, and forgotten in a jacket pocket, and it has to be comfortable, because my ear canals are small and sore and almost everything has hurt me at some point.
So this is not a spec sheet roundup. It is the list I hand to friends who ask what to buy, with the reasoning attached.
The pair I would buy first: Sony WH-CH720N
This is the most comfortable shape of the three Sonys on this list, and comfort is not a small thing. Over-ear cups surround your ear instead of resting on it. If you have ever taken a pair off after two hours because the top of your ear felt bruised, you already know why that matters. The WH-CH720N is the model I point people toward when they want one pair to do everything: wireless, over-ear, and noise cancelling.
Noise cancelling is the headline feature, and it is also the one people buy for the wrong reasons. The question is not whether the demo in a store goes quiet. The question is whether the noise cancelling helps with your specific noise, which is usually a bus engine, a lawnmower, a fan, or a coworker. Judge it on the sounds you actually fight.
There is a second thing to check on any noise cancelling headphone, and it is the reason I never recommend buying blind. Some implementations add a faint hiss, and some make your ears feel pressurized, like the start of a yawn you cannot finish. Neither problem shows up in a product listing. Both will drive you up a wall within a week. Buy from somewhere with a return window, and give it a real week before you decide.
The other reason this is the top pick: it is a headphone, not a pair of earbuds. Nothing goes inside your ear canal. If your ears are sore and small like mine, that alone settles the argument. 
Visit on Amazon →.
The value pick: Sony WH-CH520
If you want to spend as little as possible and still get a real headphone from a company that has been making them for decades, this is the one. Wireless, on-ear, with a microphone for calls. It is the pair I would hand to a teenager, a commuter, or anyone who loses things.
On-ear is the tradeoff, and it is worth understanding before you buy. The cups rest on your ear rather than around it. That makes the headphone lighter and cheaper, and it also means the pressure shows up later in the day. Hour three is where you find out. If you wear headphones for an entire workday, step up to the over-ear model. If you wear them for a walk, a bus ride, and a few calls, on-ear is fine, and "fine" is high praise from me.
The microphone matters more than people expect. Calls are half of what these things do. A headphone that sounds great and makes you sound like you are calling from the bottom of a well is not a good headphone, and the only way to know is to make actual phone calls with it. Not voice memos. Calls.
Battery is the other spec I check before anything else, and the reason is simple: a pair that dies after two hours is useless no matter how good it sounds. Ignore the number on the box. Run your own drain test at the volume you actually listen at, over a few days, and see whether it matches. 
Visit on Amazon →.
The colorway question: WH-CH520 in Cappuccino
This is the same headphone as the black WH-CH520, in a different finish. I am listing it separately because color is the one spec nobody mentions and everybody cares about. Black plastic looks like gear. Cappuccino looks like something you would not mind wearing to a coffee shop. If the choice comes down to two listings with identical hardware, buy the one you will actually put on your head, because a pair that stays in the drawer is the most expensive pair you own. 
Visit on Amazon →.
The wired holdout: Apple EarPods with USB-C
I resisted this one for years on principle, and the principle was correct: wired still sounds better, and there is no latency, no pairing, no charging case, and no battery to age out. The EarPods plug into USB-C, which means the port that killed the headphone jack is now the port that brings wired back. That is a strange turn of events and I am not complaining.
Here is what wired buys you that no wireless pair can. It cannot run out of charge in the middle of a call. It cannot drop out when you walk past a busy intersection. It cannot pair to the wrong device in your bag. And it cannot greet you with a dramatic voice announcement when you turn it on, because there is nothing to turn on. You plug it in. That is the whole interaction, and honestly it is the most reliable audio experience I own.
The built-in remote handles music, phone calls, and volume from the cable, so you are not reaching for your phone every time a song ends. The catch is the cable itself. Cables snag on doorknobs, get chewed by cats, and get yanked out of your ear when you stand up. That is why wired lost, and it is worth being honest about it before you buy. 
Visit on Amazon →.
How I test
Every pair goes through the same gauntlet, and it is the same one I would hand you if you were standing in my kitchen.
Battery first. How long does it actually last at normal listening volume, not the volume in the marketing photo? A pair that dies after two hours is a paperweight with a driver in it.
Volume floor second. This is the test nobody runs and everybody suffers through. Can the quietest setting actually get quiet? If the minimum volume is still loud enough to blast my eardrums, the pair is useless for night listening, and no amount of good sound fixes it.
Comfort third, over at least a week, on walks and workouts. Not in a chair for ten minutes. Real use. If it hurts my ear canals or slides out mid-walk, nothing else about it matters, and I will say so.
Calls fourth. Actual phone calls, on a street, with traffic. Microphone quality is half the product.
And the small stuff last, because the small stuff is what you live with. Any obnoxious power-on announcement. Any touch control that ignores you so you grab your phone anyway. Any charging case marketed as extending playtime when it is really just recharging. Those annoyances do not show up in a spec comparison, and they are the reason people stop using a pair they paid for.
What the tradeoffs actually look like
Three of these four are wireless, and I still believe wired sounds better. That contradiction is the whole point of this guide. Wireless is the practical reality, so the job is picking the wireless pair that annoys you least.
Over-ear versus on-ear is the biggest comfort decision here, and it is not close. Over-ear surrounds the ear. On-ear presses on it. If you have sensitive ears or you wear headphones for hours, pay for the over-ear model. If you wear them in short bursts, the on-ear model is lighter and cheaper and you will never think about it again.
Noise cancelling is worth it only if you have a specific noise problem. It is genuinely useful on a plane, a bus, or in a loud office. It is dead weight if you listen at home in a quiet room, and it is one more thing to charge.
Wired is the reliability play. No battery, no pairing, no latency, no dropouts, and no charging case to lose. The cable is the entire downside, and it is a real one.
The thing I would tell you to ignore is the marketing language. Magic cases, dramatic voice greetings, and spec sheets that promise the world are noise. What matters is whether the pair is still comfortable in week two, whether the battery survives a normal day, and whether the quietest volume setting is quiet enough to fall asleep to. That is the test, and no listing answers it for you.
The headphones and earbuds reference table
This is the table I keep for the pairs I recommend, with the tradeoff written next to each one. Battery figures and prices change, so check the listing before you buy.
| Pair | Type | Charging | Best for | The tradeoff |
|---|---|---|---|---|
| Visit on Amazon → Sony WH-CH720N |
Over-ear, wireless, noise cancelling | Rechargeable, run your own drain test | Long listening, commuting, loud rooms | Costs the most here, and noise cancelling is one more thing to charge |
| Visit on Amazon → Sony WH-CH520 (Black) |
On-ear, wireless, with mic | Rechargeable, run your own drain test | Walks, chores, calls, losing them without grief | The cups rest on your ears, so hour three is the test |
| Visit on Amazon → Sony WH-CH520 (Cappuccino) |
On-ear, wireless, with mic | Rechargeable, run your own drain test | Same as the black pair, different finish | Identical hardware, so buy the color you will actually wear |
| Visit on Amazon → Apple EarPods (USB-C) |
Wired earbuds, USB-C plug, built-in remote | None, and that is the point | Calls, editing, any device with a USB-C port | The cable, which snags on everything and dies first |
Should you buy the Sony WH-CH720N?
Yes, if you want one pair to cover the whole day and your ears are the sensitive part of your body. Over-ear cups surround the ear instead of pressing on it, and that is the difference between a pair you forget about and a pair you take off every two hours. Noise cancelling is the other reason to buy it, and it is genuinely useful on a bus, a plane, or in a loud office.
Buy it from somewhere with a return window, and give it a full week. Check whether the noise cancelling hisses or makes your ears feel pressurized, and check whether the battery survives your normal day at your normal volume. If both answers are good, you are done. If either one bothers you, send it back and buy the on-ear model instead. Visit on Amazon →.
Should you buy the Sony WH-CH520?
Yes, if you want to spend as little as possible without buying junk. Wireless, on-ear, with a microphone, in black or cappuccino. It is the pair I would hand to a commuter, a student, or anyone who has lost headphones before and will lose them again. Losing a cheap pair is annoying. Losing an expensive pair ruins your week.
Just know what you are getting. On-ear means pressure on your ear, and if you wear headphones for six hours straight you will feel it. It also means no noise cancelling, so a loud bus is still a loud bus. If those two things do not bother you, this is the best value on the list, and the cappuccino finish is the same headphone for anyone who does not want another black plastic pair. Visit on Amazon →.
Should you buy the Apple EarPods with USB-C?
Yes, if your phone still has a port and you are tired of charging things. This is the pair for the person who wants to plug in and be done: no pairing, no battery, no latency, no dropouts when you walk past a busy intersection, and a built-in remote for music, calls, and volume on the cable itself.
I still think wired sounds better, and I own the wireless reality anyway. If you split your listening between a desk, a phone, and a laptop that all have USB-C, this is the least complicated audio purchase you can make. The cable is the whole catch, and it is a real one, but it is also the only part of this list that will never need to be charged before a call. Visit on Amazon →.