As of 2025 (today: Sept 10, 2025), these are widely recommended as the most comfortable headphones — grouped by use case so you can pick what matters most to you:

Top comfortable picks

• Sony WH‑1000XM6 — Best overall for long wear + top-tier ANC; lighter headband and low clamping force make them easy to wear for many people. (rtings.com, techgearlab.com)
• Bose QuietComfort Ultra (Gen 2) — Plush, very glasses‑friendly earcups and one of the softest fits for travel/office use; Bose refreshed the Ultra line this year. (rtings.com, theverge.com)
• Meze 99 Classics — Exceptionally comfortable, lightweight build and plush pads that reviewers and retailers often nominate as “most comfortable” for long home listening. (crutchfield.com)
• Sennheiser HD 660S2 — Open‑back audiophile option with velour pads and low fatigue for long critical listening sessions (great at home/studio). (rtings.com)
• Anker / Soundcore Life Q20 — Best budget pick for all‑day comfort (memory‑foam pads, very light and affordable). Good option if you want comfort without premium price. (rtings.com, techradar.com)
• Apple AirPods Max — Very roomy earcups and premium materials (comfortable for many), but heavier than rivals so comfort varies by user/head/neck strength. Good if you prioritize build and Apple ecosystem. (techgearlab.com, theverge.com)

Quick buying tips (comfort-focused)

• Try with glasses or your usual hairstyle: clamping force and pad shape affect glasses wearers differently. Retail tests & fit factors matter. (crutchfield.com)
• Consider ear‑cup depth: shallow cups can press on ears during long sessions (important for people with larger ears). (rtings.com)
• Weight vs. clamp trade‑off: lighter cans often feel less fatiguing, but too‑loose fit can reduce isolation and stability. (rtings.com)
• Use return windows: comfort is personal — buy from retailers with easy returns or try in‑store when possible. (Many reviewers recommend this approach.) (techgearlab.com, rtings.com)

If you tell me which you care most about (travel, flights, glasses, audiophile listening, budget), I’ll narrow this to 2–3 best picks for your exact needs and typical use.