I’ve struggled to find an answer to that myself. I think this year I’m going with a leather trucker-style jacket with a shirt and tie underneath and a pair of single layer jeans with hip armour. At least that offers a bit more protection that a Harris Tweed!
You can’t really. I’ve ridden from Winchester down to Poole in Dorset three times in a suit, tweed jacket and once in plus fours.
I’ve worn an old sheepskin flying jacket and a striped blazer.
Just don’t fall off 
I suppose the only sensible option is to get a set of armoured under garments and wear ‘normal’ clothes over the top.
I did try that last year with my Tweed jacket but I looked like a complete Knob! So I settled for a less dapper leather jacket instead (with no armour)
I have some Knox armoured shorts, which I have worn to at least two DGR’s. They are getting a bit tight now!
I will be wearing single layer jeans this time with hip armour, not sure about the jacket yet.
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I now have a solution to my dilemma regarding being protected on the ride to and from the DGR start and finish.
Duh, I have a van so the bike will be going in the back and I have prearranged parking at the finish. 
However, I was then telling Mrs B and she said “why don’t I come with you and bring the dog?” This may not seem like a revelation but she hasn’t been with me on the ride since 2018 so I didn’t think she would be interested in tagging along, or driving the van for that matter.
Bonus, all sorted for the 21st then 
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It’s about a 48 mile ride into York for me if I avoid the A19 and go via Helmsley.
I think there are four of us from our local bike group going from this area, so we may ride down together. Main problem will be keeping warm in none bike gear at that time in the morning!
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The Aberdeen ride went passed me today, about 30 of em, mostly Triumphs. Saw one going ahead of the rest, with a surprise in store, a custom Harley, side stand on the right, and DOWN. Dont know how it ended.
9.00 am start from Thornaby for the York DGR.
Decent turn-out at A1 Moto Triumph - about 220 riders and a good mix of bikes.
Me half way round at Cliffords Tower
Finished at Dick Cravens motorcycle museum and then a stop off at Helmsley on the way back
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Thank you - yes we did a very enjoyable day in the sunshine and somehow the four of us more or less kept together
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I kinda like that Tart’s handbag Valkyrie 
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I know what you mean, not my thing at all but there’s definitely something about it. It belongs to my mate Des and it is immaculate for it’s age
He changed the exhaust baffles for more open ones and as it’s a flat six, it sounds like an old Porsche when he accelerates. 
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Shinko crossply?