My Favorite Things: Headphones Edition

As someone who spends most of my day in meetings, I've gone through way too many headphones trying to find ones that actually work for long wear times and professional calls. These are the headphones that have actually stuck around and proven themselves useful in my daily life

Quick Picks: No Fluff

Here are the best headphones that are in my regular rotation:

Best Everyday Headphones - Shokz OpenRun Pro 2 Mini

Best Compact Headphones - AirPods Pro 2

Best Travel Headphones - Sony WH-1000XM4

Here's a detailed review of each one, including what I like, what's annoying, and when I actually use them.

Shokz OpenRun Pro 2 Mini Review

Best Everyday Headphones for Work

Buy Here

Best Buy | REI

These bone conduction headphones have become my go-to choice for daily use. I originally discovered these after my Airpods 3 stopped working, and I needed headphones I could wear all day without ear fatigue.

I went with the Mini version because I have a small head, but the regular OpenRun Pro 2 works just the same if you need a larger fit. The functionality and features are identical between the two sizes.

Like many remote workers, I spend most of my day on video calls, and earbuds start hurting my ears and making them sweat after a couple of hours. These completely solved that problem while delivering excellent call quality.

This headphone removes every excuse I had about wearing headphones all day. Plus, I can stay aware of my surroundings during outdoor activities.

Pros

• Open-ear design means no ear fatigue or sweating during long work days

• Excellent microphone quality that doesn't pick up background noise

• Good battery life for all-day use

• Can wear them at comfortable volume without disturbing others nearby

• Perfect for outdoor workouts and walks where situational awareness matters

Cons

• Can only pair with 2 devices at a time, and switching out those devices can be annoying

• Bulky design makes them less ideal for travel packing

• No button to skip to the next song

• Sound can be heard by others nearby if volume is very loud

When I use them:

• Work Zoom meeting and calls all day

• Outdoor walks when I want to hear traffic and people around me

• Any time I need to wear headphones for extended periods of time without ear fatigue

AirPods Pro 2 Review

Best Compact Headphones for Travel

Buy Here:

Best Buy | Apple

When I need noise cancellation on the go, these are my first choice. The compact size makes them easy to throw in any bag, and I don't have to worry about them taking up space.

The transparency mode is great for running errands when I want to listen to music but still chat with sales clerks or stay aware of what is happening around me.

Pros

• Active noise cancellation

• Seamless integration across all Apple devices (iPhone, iPad, MacBook)

• Effective transparency mode for situational awareness

• Compact size

• Great for workouts with secure fit

Cons

• Some ear discomfort after 1-2 hours of continuous wear

• Shorter battery life than other headphones

When I use them:

• Working out

• Running errands

• Traveling (I will bring both these and the Sony WH)

  
  

Sony WH-1000XM4 Review

Best Travel Headphones with Noise Cancellation

Buy Here:

Best Buy | Sony

Anytime I'm on an airplane or want to completely block out noise for a longer period of time, these over-ear headphones are unmatched. The noise cancellation is incredible at drowning out engine noise and general airport chaos, and the comfort allows for hours of continuous use during long flights.

Pros

• Incredible noise cancellation technology

• Comfortable fit

• Long battery life

• Over-the-ear design

Cons

• Transparency mode isn't great

• Touch controls can be overly sensitive

• Larger size takes up significant space when traveling

When I use them:

• Reading a book or playing video games where I want full immersion

• ANY airplane ride - even though they take up bag space, these come with me on every flight

Headphone Reviews: What Didn't Work

Bose Ultra Open Earbuds

The sound quality was impressive, but the microphone picked up excessive background noise. Since I am on calls or in meetings all the time, these weren't a good fit for me. With the price point, I wasn't interested in these if I couldn't use them for calls. I've talked to people who don't need to use the microphone feature who speak highly of these.

AirPods 4

I wanted these to replace my beloved Airpod 3, but the slightly larger size caused discomfort after 1-2 hours. Given the comfort limitations, the AirPods Pro 2 offers better value for similar wearing time.

Airpods 3

These were actually excellent and part of my regular rotation until they stopped working. I traded them for the Airpods 4, which led me to discover the Shokz as a better long-term solution.

Original Beats by Dre

These were my first premium over-ear headphones that I received as a gift, and they really started my headphone journey. I actually enjoyed the sound quality, but the padding started chipping after about a year. This was several years ago, so they may use different materials in the new models. For comparison, my Sony headphones are in their fifth year and are just now starting to lose some cushioning, but no material cracking.

How I Think About Headphone Selection

I've found that having different headphones for different situations works better than trying to find one perfect pair. My work day looks different from my travel day, which looks different than my cozy-at-home day.

What matters most is matching the headphones to how you'll actually use it. I spend most of my day in meetings, so all-day comfort and microphone quality are non-negotiable. When I'm traveling, size and noise cancellation become priorities. For focused work or entertainment, sound immersion wins.

I completely understand that not everyone wants or can have multiple headphones, and I know people have different comfort preferences and use cases. What works for my particular combination of long work calls, outdoor activities, and varied environments might be totally different from what works for you.

Keep in mind: Be sure to advocate for yourself when it comes to fit and comfort. What works for one person's ear shape might not work for yours. Also, if you take a lot of calls for work, test the microphone quality before committing to a pair.

One thing that made my headphone testing possible: many retailers offer 10-30 day return policies. Be sure to check your store's specific policy and ask about any restocking fees upfront. This is how I was able to try different options, decide they weren't right for me, and exchange them for something better.

Every person approaches audio gear differently, and I've learned that my research-everything tendency actually serves me well here. These three cover all my bases, and honestly, I've stopped trying to find the one perfect headphone that does everything.

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Coming from someone who researches everything thoroughly, I hope this breakdown helps you think through what might work for your specific situation. I'm constantly learning what works best for different scenarios, and it's an ongoing journey rather than finding the perfect system.