+1. I have a pair of Deer shoes I'm very happy with.
MTM or from your own last or off the rack standard?
I walk past the Cloakroom in Sydney super regularly -- what are the prices like for Grenson? I've always been reluctant to head on inside -- I feel like they dick-ride virtually every online trend they can, and a little too late at that.
The Pistols at Dawn stuff looks okay, though.
A few random thoughts
Sadly, as you have already discovered it is a wasteland when it comes to fine menswear in Australia. Visiting a mtm or bespoke tailor will only land you in more debt and disapointment. Your best bet is to wander into Harrolds in Melbourne and actually try everything on there. I have tried most options in Sydney and found myself frustrated and deluded. Try Raffaele Caruso, soft shoulder construction their cheaper of their RTW collection, then jump into Brioni, Kiton and Tom Ford. Don't look at the prices, take the garments to the dressing room and take photos of the tags in the inside jacket pocket of the garments that fit you best.
If there in anything remotely working for you, say thanks and jump on style forum and e-bay and look for that sports coat, blazer or suit in that size. You will often find garments NWT at a fraction of the cost. Let me give you an example. I tried a Tom Ford suit in Harrolds at list $7700.00. It was lovely and my exact size was 44 Regular. Only fools would be silly to pay list at Harrolds... Instead I found the exact suit, here in SF, NWT for $2800 (make an offer). I offered $2300! He accepted..
The suit was shipped and was exactly as described. Tom Ford is made in the Zegna factory and I have two mtm Zegna that are really well constructed so i knew I was getting something that will last for 3-4 years with gentle wear. A good cost per wear.
Ironically the best cost per wear item is still a bespoke navy blazer I did have made by a tailor in Sydney, named Victor Allacqua in Double Bay. The fabric is Holland and Sherry Cashmere wool and it is the best staple in my wardrobe, although it is heavily laden with the 1950's style shoulder pads, making it hard to wear with denim or casually with chinos and the like. Navy blazer teamed with incotex trousers in different shades of charcoal is the best ensemble for mating ties, pocket squares and of course brown shoes. If you are going bespoke try and find out who is making the garment for you. It is unlikely to be the charming guy seducing you in the store. Instead it is likely to be a dinosaur of an old European who may or may not be skilled in the art of jacket making. If he has a hunchback, speaks abominable English then you may actually be in luck.
On another note:
What I do find is that posture is paramount when it comes to finding garments that work. The minute you start to do more regular exercise that assists in creating a more universal posture the more likely you will get a ready to wear garment to work for you. This has been my experience, which has meant I have been able to venture into to RTW garments having taken up yoga 4 years ago.
As for Herringbone, you might find yourself better off admiring the skilful merchandising from outside the store and walking on by...