Short answer: look for ankle boots with a roomy toe box, low or block heel (≤3–4 cm), cushioned/removable insoles with good arch support, and a flexible shock‑absorbing sole. Brands that regularly meet those criteria and are worth trying in Australia are Blundstone, ECCO, Clarks and podiatrist‑recommended lines such as Vionic — plus styles with removable footbeds so you can insert your own orthotic if needed. (CleverHiker.com)

Recommended boots to try (why they’re comfortable)

• Blundstone (Original/Classic and work styles) — slip‑on Chelsea designs with cushioned footbeds, shock‑absorbing midsoles and roomy toe boxes; many wearers find them comfortable for long days on their feet. Good for everyday walking and Aussie conditions. (CleverHiker.com)
• ECCO (ankle/chelsea ranges) — engineered footbeds (FluidForm/Fluidform technology), soft leathers and flexible soles that aim to reduce pressure and give a more anatomical fit. Often have removable insoles. Good if you want a soft, supportive leather boot. (au.ECCO.com)
• Clarks — many Clarks ankle boots use cushioned “Cloud” or Cushion Soft footbeds and are frequently recommended by foot experts for everyday comfort and shock absorption. Good choice if you need soft step‑in comfort. (people.com)
• Vionic (and other podiatrist‑endorsed lines) — designed with built‑in orthotic support and arch contouring; especially helpful if you have plantar fasciitis, high arches or need extra arch support. (people.com)

How to pick a pair that won’t hurt

• Measure and try late afternoon: feet swell during the day; shop in the afternoon for the truest fit.
• Leave ~1 cm (a thumb’s width) of toe room for walking; avoid pointy toes if comfort is priority.
• Choose block/low heels (≤3–4 cm) or flat platforms — they cut strain on forefeet and ankles.
• Look for removable insoles so you can insert custom orthotics or a higher‑quality insole.
• Prioritise a firm but cushioned midsole and a sole with some flex at the ball of the foot (too stiff or too floppy both cause issues).
• Check return policy: buy from stores with easy returns so you can test at home and return if they rub or hurt.

Quick fitting checklist when you try them on

• Walk 10–15 minutes on a hard surface in the store (or at home if ordering online).
• Make sure no rubbing at the Achilles, ankle bone or toe seams.
• Heel should slip a little on first wear but not more than ~1 cm; excessive slip causes blisters.
• Test the width — many comfortable boots come in wide options or have a stretch panel (elastic gore).

If you have a foot condition

• Bunions/wide forefoot: choose wide‑toe‑box styles (look for brands offering wide fits).
• Plantar fasciitis/arch pain: favour boots with built‑in arch support (Vionic, podiatrist lines) or use your orthotics.
• Sensitive skin/rubbing: soft leather or textile linings and seamless toes help reduce hotspots.

Where to try/buy in Australia

• Blundstone and ECCO have official stores and online AU sites (try in person for fit). Clarks and Vionic models are widely available at major shoe retailers and department stores — shop where returns/exchanges are easy. (CleverHiker.com)

If you want, I can:

• Pick 6 specific ankle‑boot models for your needs (walking, standing all day, wide feet or dressy) and include Australian retailers and price ranges.