Short answer — buy ankle boots with a roomy toe box, a cushioned/removable insole and low/moderate heel, and pick one of these comfort-focused models that reviewers and podiatrists recommend:

Top comfortable ankle-boot picks (by need)

• ECCO Shape / Sculpted ankle boots — leather, anatomical footbed and ECCO’s FluidForm cushioning: great for all‑day walking and city wear. (us.ecco.com)
• Clarks Orinoco (Orinoco 2/3) — cushioned Contour Cushion footbed, removable insole and a forgiving sole; widely recommended for comfort. (clarks.com)
• Vionic (e.g., Vienna / Rhiannon zip ankle boots) — built‑in orthotic arch support and a stable sole; good if you need serious arch/heel support. (amazon.com)
• HOKA Anacapa (Breeze Mid / Anacapa line) — a very cushioned, lightweight mid/ankle boot with HOKA foam and Vibram outsole (best if you walk/hike a lot). Note: some users report hardware around the ankle can rub — try them on and walk around before buying. (hoka.com)
• Orthofeet / Aetrex — models with removable/customizable insoles and multiple width options; podiatrist‑recommended for plantar fasciitis or other foot conditions. (verywellfit.com)
• Dr. Scholl’s Rate Zip — good budget pick with branded cushioning and generally roomy fit for everyday wear. (realsimple.com)

Why these work

• Removable insoles let you swap in custom orthotics or a better over‑the‑counter insert.
• Roomy toe box + correct width prevents pinching and bunion pain.
• Cushioned midsole and stable heel reduce impact on heels, knees and forefoot. (These are the features podiatrists and orthopaedic groups recommend.) (orthoinfo.aaos.org)

Fit & buying tips so boots don’t hurt

• Try them at the end of the day (feet swell) and wear the socks you’ll actually use. (orthoinfo.aaos.org)
• Walk at least 5–10 minutes in the store (or during the trial period) to check for rubbing at the collar/ankle and pressure points. (stridewise.com)
• Look for: removable footbed, a stable low heel (≤1–1.5"), padded collar/tongue, and a roomy/rounded toe box. (verywellfit.com)
• If leather is stiff, soften/stretch before long wear (boot stretcher, leather conditioner, or short home break‑in under guidance). Baylor College of Medicine/podiatrists give safe break‑in tips. (bcm.edu)
• Keep returns/exchanges in mind — buy from retailers with free returns so you can test at home.

If you have a specific issue

• Plantar fasciitis or heel pain: Aetrex, Vionic or Orthofeet models with strong arch support and removable orthotics are good starting points. (livestrong.com)
• Wide feet: choose brands that offer wide sizes (Orthofeet, some Clarks, ECCO, Dr. Scholl’s). (verywellfit.com)

If you want, tell me roughly your budget and whether you need them for daily walking, commuting, work (standing all day), or hiking — I’ll narrow these recommendations to 2–3 specific models and where to buy them with the best return policy.