Short answer: pick podiatrist-designed / orthotic-friendly brands and low, wider heels. Top comfortable heel options available in Australia right now are:

1. FRANKIE4 (Australian, podiatrist‑designed) — best for everyday work heels and pumps (models like Juliett, Marlow, Cleo). Their shoes use multi‑layer cushioning, arch support and removable/adjustable insoles so you can use your own orthotic if needed. (frankie4.com)

2. Sole Bliss — specialises in “pain‑free” heels (memory‑foam layers, a bunion‑bed stretch panel and shock‑resistant heels). The brand is sold to Australian customers (AU shipping) and is widely recommended for people who need extra padding/room up front. Good pick if you need extra forefoot cushioning or have bunions. (style.nine.com.au)

3. Vionic — an orthotic/biomechanics brand that now makes heels (kitten and block heels) with built‑in supportive footbeds (deep heel cup, forefoot cushioning). They have an Australian site and heels with moderate heights (≈2–2.5"). Great if you need built‑in arch support. (au.vionicshoes.com.au)

4. Clarks — classic comfort brand with cushioned footbeds, wedges and low block heels (their Arla/Cloudsteppers tech is popular). Ideal if you want softer insoles and a stable heel. (clarks.com.au)

5. Bared Footwear (AU) — podiatrist‑founded Australian brand that designs “dressy” heels with hidden support and removable insoles for orthotics. Good for stylish event heels that are kinder on feet. (baredfootwear.com)

6. Hush Puppies — widely available in Australian department stores (Myer etc.) and known for padded insoles and moderate, wearable heel styles (block/low pumps). Good budget‑friendly option. (myer.com.au)

How to choose the least‑hurting heel (quick checklist)

• Aim for lower heels: podiatrists generally recommend around 2" (≈5 cm) or less for long wear; anything higher increases pressure on the forefoot. Choose kitten heels, low blocks, wedges or platforms. (health.yahoo.com)
• Prefer a block heel or platform over a stiletto (more surface area = less pressure, more stability). (byrdie.com)
• Look for: cushioned insole, arch support, roomy/wider toe box (avoid very pointy toes), leather/suede uppers that will stretch a little. (instyle.com)
• Removable footbeds are a bonus (lets you drop in orthotics). (shannonsshoes.com.au)

Practical comfort hacks (use with any heels)

• Add a thin gel metatarsal pad or full‑length cushioned insole for ball‑of‑foot relief.
• Use heel grips to stop slipping and blisters.
• Buy late afternoon/evening when feet are slightly swollen so fit is true. (byrdie.com)
• Break new heels in at home on carpet for short periods before a long event.
• Rotate shoes; don’t wear the same pair every day.

If you want, I can:

• Pick 3‑5 exact models in your size range or price point (I can check current stock/prices at The Iconic, Myer, David Jones, Vionic AU, Frankie4, Sole Bliss and link product pages).
• Or suggest specific gel inserts/brands that work well in heels (thin met pads, full‑length memory foam or orthotic 3/4 insoles).

Which would you prefer?